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Chemical Structure| 18362-64-6 Chemical Structure| 18362-64-6
Chemical Structure| 18362-64-6

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CAS No.: 18362-64-6

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Product Details of [ 18362-64-6 ]

CAS No. :18362-64-6
Formula : C9H16O2
M.W : 156.22
SMILES Code : CC(C)C(CC(C(C)C)=O)=O
MDL No. :MFCD00015040
InChI Key :CEGGECULKVTYMM-UHFFFAOYSA-N
Pubchem ID :87597

Safety of [ 18362-64-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1224
Packing Group:Ⅲ

Application In Synthesis of [ 18362-64-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 18362-64-6 ]

[ 18362-64-6 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 563-80-4 ]
  • [ 97-62-1 ]
  • [ 18362-64-6 ]
YieldReaction ConditionsOperation in experiment
77.3%Chromat. With potassium tert-butylate; In DMF (N,N-dimethyl-formamide); at 50℃; for 11h;Heating / reflux; In a 1-liter four-necked flask, 103 g of DMF and 1.33mol (149 g) of tert-butoxypotassium were placed, and theywere heated up to 50C with stirring by a mechanicalstirrer. Then, a liquid mixture consisting of 2.64 mol(307 g) of ethyl isobutyrate and 0.88 mol (75.6 g) of 3-methyl-2-butanone, was added by a dropping funnel over aperiod of 3 hours, followed by further stirring for 8hours under heating. It was confirmed by gaschromatography that 2,6-dimethyl-3,5-heptanedione was produced in an amount of 0.68 mol (107 g) in the solution(yield: 77.3% (based on 3-methylbutanone)).
  • 2
  • [ 18362-64-6 ]
  • [ 65534-62-5 ]
  • [ 125873-95-2 ]
  • 3
  • [ 18362-64-6 ]
  • (-)-5-hydroxy-2,6-dimethyl-3-heptanone [ No CAS ]
  • [ 128899-83-2 ]
  • [ 125873-95-2 ]
  • 6
  • [ 18362-64-6 ]
  • [ 17536-00-4 ]
YieldReaction ConditionsOperation in experiment
100% With hydrazine; In ethanol; at 20℃; for 2h; Hydrazine (330 mg, 10 mmol) was added to a solution of 2,6-dimethylheptane-3,5- dione (1.6 g, 10 mmol) in ethanol (40 mL) at room temperature. After 2 hours, the reaction was concentrated in vacuo to afford 3, 5-diisopropyl-lH-pyrazole (1.5 g, 10 mmol, yield: 100%) which was used in the next step without further purification. MS: m/z 153.1 (M+H+).
  • 8
  • [ 5153-67-3 ]
  • [ 18362-64-6 ]
  • 3-isopropylcarbonyl-5-methyl-1-nitro-2-phenyl-4-hexanone [ No CAS ]
  • 9
  • [ 187737-37-7 ]
  • [ 18362-64-6 ]
  • 3-isobutyryl-2-isopropyl-5-methylfuran [ No CAS ]
  • 3-isopropylidene-2,6-dimethyl-3,5-heptanedione [ No CAS ]
  • 10
  • [ 74-85-1 ]
  • [ 18362-64-6 ]
  • 2,6-dimethyl-4-ethylidene-3,5-heptanedione [ No CAS ]
  • 11
  • [ 5162-44-7 ]
  • [ 18362-64-6 ]
  • 2,6,6-trimethyl-9-decene-3,5-dione [ No CAS ]
  • 12
  • [ 18362-64-6 ]
  • [ 91110-24-6 ]
  • 4-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2,6-dimethyl-heptane-3,5-dione [ No CAS ]
  • 13
  • [ 18362-64-6 ]
  • [ 112197-15-6 ]
  • [ 924312-02-7 ]
YieldReaction ConditionsOperation in experiment
20% With caesium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 120℃; for 60h; (1) Production of 2-methoxy-3-(4-(trifluoromethoxy)phenoxy]pyridine: 2,6-Dimethylheptane-3,5-dione (0.019 mL, 0.085 mmol), copper(I) chloride (43 mg, 0.43 mmol) and cesium carbonate (554 mg, 1.70 mmol) were added to an NMP (2 mL) solution of 3-iodo-2-methoxypyridine (200 mg, 0.85 mmol), and stirred for 2.5 days in the presence of nitrogen at 120C. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, then the insoluble matter was removed by filtration through Celite, followed by extraction with ethyl acetate. The obtained organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, then dried with anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure, then the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:0 to 17:3) to obtain the entitled compound (49 mg, 20 %). Mass Spectrum (ESI): 286.0 (M+H).
  • 14
  • [ 18362-64-6 ]
  • copper(II) nitrate [ No CAS ]
  • 2,6-dimethyl-heptane-3,5-dione; copper(2+) chelate (2:1) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.2% With sodium methylate; In methanol; at 20℃; for 1h; In 20 g of methanol, 7.20 g (0.0400 mol) of a sodiummethylate methanol solution of 30% purity was dissolved,and the resulting solution was cooled to room temperature. Then, 7.19 g (0.0400 mol) of <strong>[18362-64-6]2,6-dimethyl-3,5-heptanedione</strong> of 87% purity was dropwise added withstirring. Then, 4.83 g (0.0300 mol) of Cu (N03) 2- 6H20 wasadded. After the reaction was conducted for 1 hour, 100g of water was added over a period of 30 minutes,followed by stirring for 1 hour. The resulting crystalswere filtered off and dried. Thus, 7.23 g (yield: 88.2%)of bis(2,6-dimethyl-3,5-heptanedionato)copper wasobtained.
  • 15
  • [ 18362-64-6 ]
  • [ 7782-61-8 ]
  • tris(2,6-dimethylheptane-3,5-dionato)iron(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.9% With sodium methylate; In methanol; at 25 - 28℃; for 1.5h; In 178 g of methanol, 66.9 g (0.372 mol) of a sodiummethylate methanol solution of 30% purity was dissolved,and the resulting solution was cooled to room temperature.Then, 66.0 g (0.377 mol) of <strong>[18362-64-6]2,6-dimethyl-3,5-heptanedione</strong>of 88% purity was dropwise added with stirring. To themixture, a solution obtained by dissolving 50.0 g (0.124mol) of Fe(N03)3-9H20 of 99% purity in 12.0 g of methanolwas added at a temperature of 25 to 28C over a period of30 minutes. The reaction was conducted for 1 hour, andthe crystals precipitated were filtered off. To theresulting solution, 400 g of water was dropwise addedover a period of 1 hour and 30 minutes. After thedropwise addition was completed, stirring was performedfor 1 hour. The resulting crystals were taken out by centrifugation and then dried. Thus, 62.0 g (yield:95.9%) of tris(2, 6-dimethyl-3,5-heptanedionato)iron wasobtained.
  • 16
  • [ 18362-64-6 ]
  • [ 10026-11-6 ]
  • tetrakis(2,6-dimethyl-3,5-heptanedionato)zirconium [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.5% In methanol; at 20℃; for 1.08333h; To 300 g of methanol, 77.1 g (0.429 mol) of <strong>[18362-64-6]2,6-dimethyl-3,5-heptanedione</strong> of 87% purity was dropwiseadded with stirring. To the resulting solution, asolution, which had been obtained by dissolving 25.0 g(0.106 mol) of ZrCl4 of 99% purity in 100 g of methanoland cooled to room temperature, was dropwise added over aperiod of about 5 minutes. The reaction was conductedfor 1 hour with stirring, and 1000 g of water was addedover a period of 1 hour. Then, stirring was performedfor 1 hour. The resulting solution was adjusted to pH6.6 with a 20% NaOH solution. The resulting crystalswere collected by centrifugation and then dried. Thus,74.5 g (yield: 97.5%) of tetrakis (2, 6-dimethyl-3,5-- heptanedionato) zirconium was obtained.
  • 17
  • [ 13494-98-9 ]
  • [ 18362-64-6 ]
  • yttrium tris(2,2,6,6-tetramethyl-3,5-heptanedionate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.2% With sodium methylate; In methanol; at 25 - 28℃; for 1.5h; In 51.4 g of methanol, 14.5 g (0.081 mol) of asodium methylate methanol solution of 30% purity wasdissolved with stirring, and the resulting solution wascooled to room temperature. Then, 12.65 g (0.081 mol) of<strong>[18362-64-6]2,6-dimethyl-3,5-heptanedione</strong> of 97% purity was addedlittle by little. To the mixture, a solution obtained bydissolving 12.63 g (0.0268 mol) of Y(N03)3-6H20 of 81.3% purity (determined by quantitative analysis) in 63.2 g ofmethanol was added at a temperature of 25 to 28C over aperiod of 30 minutes. The reaction was conducted for 1hour, and the crystals precipitated were filtered off.The separated crystals were subjected torecrystallization using ethyl butyrate as a solvent.Thus, 7.46 g (yield: 50.2%) of tris(2,6-dimethyl-3,5-heptanedionato)yttrium was obtained
  • 18
  • [ 18362-64-6 ]
  • C84H88Cl2Ir2N4 [ No CAS ]
  • C51H59IrN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium carbonate; In 2-ethoxy-ethanol; at 20℃; for 24h; [0117] Example 3: Synthesis of Compound 3Compound 3[0118] Synthesis of Compound 3. Iridium dimer (2.6 g, 1.616 mmol) from the previous step, <strong>[18362-64-6]2,6-dimethylheptane-3,5-dione</strong> (2.6 g, 16.16 mmol), Na2C03 (1.713 g, 16.16 mmol) and 2- ethoxyethanol (60 mL) were stirred at room temperature for 24 h. The precipitate was filtered and washed with methanol. The solid was further purified by passing it through a silica gel plug (that was pretreated with 15% triethylamine in hexanes) and eluted with methylene chloride. 2- Propanol was added to the filtrate. The filtrate was concentrated, but not to dryness. 2.2 g of product (73%) was obtained after filtration. The product was confirmed by LC-MS.
  • 19
  • [ 18362-64-6 ]
  • di-μ-chloro-tetrakis{4,6-dimethyl-2-[3,5-bis(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}diiridium(III) [ No CAS ]
  • bis{4,6-dimethyl-2-[3,5-bis(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O')iridium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium carbonate; In 2-ethoxy-ethanol; for 4h;Inert atmosphere; Microwave irradiation; Heating; Step 4: Synthesis of Bis{4,6-dimethyl-2-[3,5-bis(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O′)iridium(III) (abbreviation: [Ir(dmtppr)2(dibm)]) [0395] Further, into a recovery flask equipped with a reflux pipe were put 30 mL of 2-ethoxyethanol, 0.89 g of [Ir(dmtppr)2Cl]2 (abbreviation) that is the dinuclear complex obtained in Step 3, 0.20 g of <strong>[18362-64-6]diisobutyrylmethane</strong> (abbreviation: Hdibm), and 0.47 g of sodium carbonate, and the air in the flask was replaced with argon. Then, irradiation with microwaves (2.45 GHz, 200 W) was performed for 60 minutes. Here, 0.20 g of Hdibm was added, and irradiation with microwaves (2.45 GHz, 200 W) was performed again for 60 minutes. The solvent was distilled off and 0.20 g of Hdibm, 0.47 g of sodium carbonate, and 30 mL of 2-ethoxyethanol were added. The air in the flask was replaced with argon. After that, heating was performed by irradiation with microwaves (2.45 GHz, 200 W) for 2 hours. The solvent was distilled off, and the obtained residue was suction-filtered with ethanol. The obtained solid was washed with water and ethanol. The obtained solid was dissolved in dichloromethane and filtered through a filter aid in which Celite, alumina, and Celite were stacked in that order. Then, recrystallization was carried out with a mixed solvent of dichloromethane and ethanol; thus, [Ir(dmtppr)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, was obtained as a dark red powder in a yield of 73%. A synthesis scheme of Step 4 is shown in (f-4). [0396] An analysis result by nuclear magnetic resonance (1H-NMR) spectroscopy of the dark red powder obtained in Step 4 is described below. FIG. 47 shows the 1H-NMR chart. These results revealed that [Ir(dmtppr)2(dibm)](abbreviation), the organometallic complex which is one embodiment of the present invention represented by Structural Formula (123), was obtained in Synthesis Example 6. [0397] 1H-NMR. δ(CDCl3): 0.78 (d, 6H), 0.99 (d, 6H), 1.41 (s, 6H), 1.96 (s, 6H), 2.24-2.30 (m, 2H), 2.35 (s, 12H), 2.42 (s, 12H), 5.07 (s, 1H), 6.46 (s, 2H), 6.78 (s, 2H), 7.04 (s, 2H), 7.18 (s, 2H), 7.47 (s, 2H), 7.49 (s, 2H), 7.67 (s, 4H), 8.77 (s, 2H). [0398] Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as an “absorption spectrum”) of a dichloromethane solution of [Ir(dmtppr)2(dibm)](abbreviation) and an emission spectrum thereof were measured. The measurement of the absorption spectrum was conducted at room temperature, for which an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation) was used and the dichloromethane solution (0.068 mmol/L) was put in a quartz cell. In addition, the measurement of the emission spectrum was conducted at room temperature, for which a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics K. K.) was used and the degassed dichloromethane solution (0.31 μmol/L) was put in a quartz cell. Measurement results of the obtained absorption and emission spectra are shown in FIG. 48, in which the horizontal axis represents wavelength and the vertical axes represent absorption intensity and emission intensity. In FIG. 48 where there are two solid lines, the thin line represents the absorption spectrum and the thick line represents the emission spectrum. Note that the absorption spectrum in FIG. 48 is the results obtained in such a way that the absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the absorption spectrum measured by putting the dichloromethane solution (0.068 mmol/L) in a quartz cell. [0399] As shown in FIG. 48, [Ir(dmtppr)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, has an emission peak at around 629 nm, and reddish orange light emission was observed from the dichloromethane solution. [0400] Next, [Ir(dmtppr)2(dibm)](abbreviation) obtained in this example was analyzed by liquid chromatography mass spectrometry (LC/MS). [0401] In the analysis by LC/MS, liquid chromatography (LC) separation was carried out with ACQUITY UPLC (manufactured by Waters Corporation) and mass spectrometry (MS) analysis was carried out with Xevo G2 T of MS (manufactured by Waters Corporation). ACQUITY UPLC BEH C8 (2.1×100 mm, 1.7 μm) was used as a column for the LC separation, and the column temperature was 40 C. Acetonitrile was used for Mobile Phase A and a 0.1% formic acid aqueous solution was used for Mobile Phase B. Further, a sample was prepared in such a manner that [Ir(dmtppr)2(dibm)](abbreviation) was dissolved in chloroform at a given concentration and the mixture was diluted with acetonitrile. The injection amount was 5.0 μL. [0402] In the LC separation, a gradient method in which the composition of mobile phases is changed was employed. The ratio of Mobile Phase A to Mobile Phase B was 90:10 for 0 to 1 minute after the start of the measurement. Then,...
  • 20
  • [ 18362-64-6 ]
  • di-μ-chloro-tetrakis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}diiridium(III) [ No CAS ]
  • bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O')iridium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate; In 2-ethoxy-ethanol; for 1h;Inert atmosphere; Microwave irradiation; Heating; Step 4: Synthesis of Bis{4,6-dimethyl-2-[3-(3,5-dimethylphenyl)-5-phenyl-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O′)iridium(III) (abbreviation: [Ir(dmdppr-P)2(dibm)]) [0278] Further, into a recovery flask equipped with a reflux pipe were put 30 mL of 2-ethoxyethanol, 0.94 g of [Ir(dmdppr-P)2Cl]2 that is the dinuclear complex obtained in Step 3, 0.23 g of <strong>[18362-64-6]diisobutyrylmethane</strong> (abbreviation: Hdibm), and 0.52 g of sodium carbonate, and the air in the flask was replaced with argon. After that, heating was performed by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent was distilled off, and the obtained residue was suction-filtered with ethanol. The obtained solid was washed with water and ethanol and recrystallization was carried out with a mixed solvent of dichloromethane and ethanol, so that [Ir(dmdppr-P)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, was obtained as a dark red powder in a yield of 75%. A synthesis scheme of Step 4 is shown in (a-4). An analysis result by nuclear magnetic resonance (1H-NMR) spectroscopy of the dark red powder obtained by the above-described synthesis method is described below. FIG. 9 shows the 1H-NMR chart. These results revealed that [Ir(dmdppr-P)2(dibm)](abbreviation), the organometallic complex which is one embodiment of the present invention represented by Structural Formula (100), was obtained in Synthesis Example 1. [0280] 1H-NMR. δ(CDCl3): 0.79 (d, 6H), 0.96 (d, 6H), 1.41 (s, 6H), 1.96 (s, 6H), 2.24-2.28 (m, 2H), 2.41 (s, 12H), 5.08 (s, 1H), 6.46 (s, 2H), 6.82 (s, 2H), 7.18 (s, 2H), 7.39-7.50 (m, 10H), 8.03 (d, 4H), 8.76 (s, 2H). [0281] Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as an “absorption spectrum”) of a dichloromethane solution of [Ir(dmdppr-P)2(dibm)](abbreviation) and an emission spectrum thereof were measured. The measurement of the absorption spectrum was conducted at room temperature, for which an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation) was used and the dichloromethane solution (0.062 mmol/L) was put in a quartz cell. In addition, the measurement of the emission spectrum was conducted at room temperature, for which a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics K. K.) was used and the degassed dichloromethane solution (0.010 mmol/L) was put in a quartz cell. Measurement results of the obtained absorption and emission spectra are shown in FIG. 10, in which the horizontal axis represents wavelength and the vertical axes represent absorption intensity and emission intensity. In FIG. 10 where there are two solid lines, the thin line represents the absorption spectrum and the thick line represents the emission spectrum. Note that the absorption spectrum in FIG. 10 is the results obtained in such a way that the absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the absorption spectrum measured by putting the dichloromethane solution (0.062 mmol/L) in a quartz cell. [0282] As shown in FIG. 10, [Ir(dmdppr-P)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, has an emission peak at around 640 nm, and reddish orange light emission was observed from the dichloromethane solution. [0283] Further, weight loss percentage of [Ir(dmdppr-P)2(dibm)](abbreviation) was measured by a high vacuum differential type differential thermal balance (TG/DTA 2410SA, manufactured by Bruker AXS K. K.). The temperature was increased at a rate of 10. C./min under a degree of vacuum of 1×10-3 Pa. As a result, the weight loss percentage of [Ir(dmdppr-P)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, was found to be 100% as shown in FIG. 37, which indicated a favorable sublimation property of the organometallic complex. As a comparative example, the weight loss percentage of Compound A in which methyl groups are not bonded to the 3-position and the 5-position is shown. A comparison with a weight loss percentage of 78% of Compound A revealed that the organometallic complex that is one embodiment of the present invention has an improved sublimation property by having the methyl groups at the 3-position and the 5-position.
  • 21
  • [ 18362-64-6 ]
  • di-μ-chloro-tetrakis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κN3]-4,6-dimethylphenyl-κC}diiridium(III) [ No CAS ]
  • bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κN3]-4,6-dimethylphenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O')iridium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With sodium carbonate; In 2-ethoxy-ethanol; for 1h;Inert atmosphere; Microwave irradiation; Heating; Step 3: Synthesis of Bis{2-[6-(3,5-dimethylphenyl)-4-pyrimidinyl-κN3]-4,6-dimethylphenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O′)iridium(III) (abbreviation: [Ir(dmdppm)2(dibm)]) [0288] Further, into a recovery flask equipped with a reflux pipe were put 30 mL of 2-ethoxyethanol, 1.09 g of [Ir(dmdppm)2Cl]2 (abbreviation) that is the dinuclear complex obtained in Step 2, 0.32 g of <strong>[18362-64-6]diisobutyrylmethane</strong> (abbreviation: Hdibm), and 0.72 g of sodium carbonate, and the air in the flask was replaced with argon. After that, heating was performed by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent was distilled off, and the obtained residue was suction-filtered with ethanol. The obtained solid was washed with water and ethanol and recrystallization was carried out with a mixed solvent of dichloromethane and ethanol, so that [Ir(dmdppm)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, was obtained as a red powder in a yield of 62%. A synthesis scheme of Step 3 is shown in (b-3). [0289] An analysis result by nuclear magnetic resonance (1H-NMR) spectroscopy of the red powder obtained by the above-described synthesis method is described below. FIG. 11 shows the 1H-NMR chart. These results revealed that [Ir(dmdppm)2(dibm)](abbreviation), the organometallic complex which is one embodiment of the present invention represented by Structural Formula (107), was obtained in Synthesis Example 2. [0290] 1H-NMR. δ(CDCl3): 0.69 (d, 6H), 0.82 (d, 6H), 1.51 (s, 6H), 2.17-2.23 (m, 2H), 2.31 (s, 6H), 2.45 (s, 12H), 5.19 (s, 1H), 6.61 (s, 2H), 7.17 (s, 2H), 7.56 (s, 2H), 7.82 (s, 4H), 8.11 (d, 2H), 8.88 (d, 2H). [0291] Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as an “absorption spectrum”) of a dichloromethane solution of [Ir(dmdppm)2(dibm)](abbreviation) and an emission spectrum thereof were measured. The measurement of the absorption spectrum was conducted at room temperature, for which an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation) was used and the dichloromethane solution (0.072 mmol/L) was put in a quartz cell. In addition, the measurement of the emission spectrum was conducted at room temperature, for which a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics K. K.) was used and the degassed dichloromethane solution (0.072 mmol/L) was put in a quartz cell. Measurement results of the obtained absorption and emission spectra are shown in FIG. 12, in which the horizontal axis represents wavelength and the vertical axes represent absorption intensity and emission intensity. In FIG. 12 where there are two solid lines, the thin line represents the absorption spectrum and the thick line represents the emission spectrum. Note that the absorption spectrum in FIG. 12 is the results obtained in such a way that the absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the absorption spectrum measured by putting the dichloromethane solution (0.072 mmol/L) in a quartz cell. [0292] As shown in FIG. 12, [Ir(dmdppm)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, has an emission peak at around 609 nm, and reddish orange light emission was observed from the dichloromethane solution.
  • 22
  • [ 18362-64-6 ]
  • di-μ-chloro-tetrakis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}diiridium(III) [ No CAS ]
  • bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O')iridium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With sodium carbonate; In 2-ethoxy-ethanol; for 1h;Inert atmosphere; Microwave irradiation; Heating; Step 4: Synthesis of Bis{4,6-dimethyl-2-[5-(2,6-dimethylphenyl)-3-(3,5-dimethylphenyl)-2-pyrazinyl-κN]phenyl-κC}(2,6-dimethyl-3,5-heptanedionato-κ2O,O′)iridium(III) (abbreviation: [Ir(dmdppr-dmp)2(dibm)]) [0411] Further, into a recovery flask equipped with a reflux pipe were put 30 mL of 2-ethoxyethanol, 0.80 g of [Ir(dmdppr-dmp)2Cl]2 (abbreviation) that is the dinuclear complex obtained in Step 3, 0.19 g of <strong>[18362-64-6]diisobutyrylmethane</strong> (abbreviation: Hdibm), and 0.42 g of sodium carbonate, and the air in the flask was replaced with argon. After that, heating was performed by irradiation with microwaves (2.45 GHz, 120 W) for 60 minutes. The solvent was distilled off, and the obtained residue was dissolved in dichloromethane and filtered through a filter aid in which Celite, alumina, and Celite were stacked in that order. Then, recrystallization was carried out with a mixed solvent of dichloromethane and methanol; thus, [Ir(dmdppr-dmp)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, was obtained as a red powder in a yield of 48%. A synthesis scheme of Step 4 is shown in (g-4). [0412] An analysis result by nuclear magnetic resonance (1H-NMR) spectroscopy of the red powder obtained in Step 4 is described below. FIG. 50 shows the 1H-NMR chart. These results revealed that [Ir(dmdppr-dmp)2(dibm)] (abbreviation), the organometallic complex which is one embodiment of the present invention represented by Structural Formula (124), was obtained in Synthesis Example 7. [0413] 1H-NMR. δ(CDCl3): 0.80 (d, 6H), 0.81 (d, 6H), 1.47 (s, 6H), 1.95 (s, 6H), 2.10 (s, 12H), 2.23-2.28 (m, 2H), 2.34 (s, 12H), 5.19 (s, 1H), 6.48 (s, 2H), 6.81 (s, 2H), 7.06 (d, 4H), 7.11 (s, 2H), 7.16 (t, 2H), 7.40 (s, 4H), 8.22 (s, 2H). [0414] Next, an ultraviolet-visible absorption spectrum (hereinafter, simply referred to as an “absorption spectrum”) of a dichloromethane solution of [Ir(dmdppr-dmp)2(dibm)](abbreviation) and an emission spectrum thereof were measured. The measurement of the absorption spectrum was conducted at room temperature, for which an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation) was used and the dichloromethane solution (0.059 mmol/L) was put in a quartz cell. In addition, the measurement of the emission spectrum was conducted at room temperature, for which a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics K. K.) was used and the degassed dichloromethane solution (0.059 mmol/L) was put in a quartz cell. Measurement results of the obtained absorption and emission spectra are shown in FIG. 51, in which the horizontal axis represents wavelength and the vertical axes represent absorption intensity and emission intensity. In FIG. 51 where there are two solid lines, the thin line represents the absorption spectrum and the thick line represents the emission spectrum. Note that the absorption spectrum in FIG. 51 is the results obtained in such a way that the absorption spectrum measured by putting only dichloromethane in a quartz cell was subtracted from the absorption spectrum measured by putting the dichloromethane solution (0.059 mmol/L) in a quartz cell. [0415] As shown in FIG. 51, [Ir(dmdppr-dmp)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, has an emission peak at around 616 nm, and reddish orange light emission was observed from the dichloromethane solution. [0416] Further, weight loss percentage of [Ir(dmdppr-dmp)2(dibm)](abbreviation) was measured by a high vacuum differential type differential thermal balance (TG/DTA 2410SA, manufactured by Bruker AXS K. K.). The temperature was increased at a rate of 10 C./min under a degree of vacuum of 1×10-3 Pa. As a result, the weight loss percentage of [Ir(dmdppr-dmp)2(dibm)](abbreviation), the organometallic complex that is one embodiment of the present invention, was found to be 100% as shown in FIG. 52, which indicated a favorable sublimation property of the organometallic complex. [0417] Next, [Ir(dmdppr-dmp)2(dibm)](abbreviation) obtained in this example was analyzed by liquid chromatography mass spectrometry (LC/MS). [0418] In the analysis by LC/MS, liquid chromatography (LC) separation was carried out with ACQUITY UPLC (manufactured by Waters Corporation) and mass spectrometry (MS) analysis was carried out with Xevo G2 T of MS (manufactured by Waters Corporation). ACQUITY UPLC BEH C8 (2.1×100 mm, 1.7 m) was used as a column for the LC separation, and the column temperature was 40 C. Acetonitrile was used for Mobile Phase A and a 0.1% formic acid aqueous solution was used for Mobile Phase B. Further, a sample was prepared in such a manner that [Ir(dmdppr-dmp)2(dibm)](abbreviation) was dissolved in chloroform at a given concentration and the mixture was diluted with acetonitrile. The injection amount was 5.0 μL. [0419] In the LC separation, a gradient method in which the composition of mobile phases is c...
  • 23
  • [ 18362-64-6 ]
  • [ 95-54-5 ]
  • [ 5851-43-4 ]
YieldReaction ConditionsOperation in experiment
55% With sodium iodide dichloride; In tetrahydrofuran; water;Reflux; General procedure: To a mixture of o-substituted (-NH2 or -SH or -OH) anilines(1.0 mmol) and appropriate 1,3-diketones (1.1 mmol) in THF(5 mL) was added 30%w/w aqueous NaICl2 (0.2 mmol, 20mol%). The reaction was allowed to remain stirred at refluxtemperature for 2-3 h. After the reaction was complete, asindicated by TLC, the mixture was cooled to room temperature.The volatiles were removed under reduced pressureand treated successively with aqueous sodium thiosulphatesolution and saturated solution of NaHCO3, and extractedby ethylacetate (2×10 mL). The combined organic phaseswere washed with brine and dried over Na2SO4 and evaporatedunder vacuum. The crude reaction mixture was purifiedby column chromatography on silica gel using petroleumether/ethyl acetate as eluents.
  • 24
  • [ 18362-64-6 ]
  • [ 60805-11-0 ]
  • 4-(2,2-bis(trifluoromethylsulfonyl)ethyl)-2,6-dimethylheptane-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In dichloromethane; at 20℃; for 2.5h;Inert atmosphere; General procedure: To a solution of carbonyl compound (1.0-2.0 equiv) in CH2Cl2 or 1,2-dichloroethane, Tf2CHCH2CHTf2(5, 0.50 mmol) was added at room temperature. After stirring at room temperature to 80 C, the reaction mixture was concentrated under reduced pressure. The resultant residue was purified by bulb-to-bulb distillation using a Kugelrohr oven to give bis(triflyl)ethylated product 4.
  • 25
  • [ 18362-64-6 ]
  • [ 40473-50-5 ]
  • [ 1632130-86-9 ]
  • [ 1632130-87-0 ]
YieldReaction ConditionsOperation in experiment
63%; 6% With sodium bisulfate supported on silica gel; In 1,2-dichloro-ethane; at 80℃; for 5h; General procedure: A mixture of -diketones 1 (6 mmol), o-hydroxybenzyl alcohols 2 (2 mmol) and NaHSO4/SiO2 (2.1mmol, 1.0 g) in dichloroethane (10 mL) was stirred at 80 C for 5 h, and then the used supportedreagent was removed by filtration. The filtrate was evaporated to leave crude product, which waspurified by column chromatography (hexane/ethyl acetate) to obtain 3.
  • 26
  • [ 18362-64-6 ]
  • C14H22O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41.2% With oxidobis(quinolin-8-olato)vanadium(IV); oxygen; In 1,2-dichloro-ethane; at 80℃; under 760.051 Torr; for 72h; General procedure: A mixture of acetylacetone (58 mmol) and catalyst (0.07-0.14 mmol,unless otherwise stated) was placed into a three-necked flask. Then theone-pot tandem reactionwas performed at 80 C or specific temperaturefor the appropriate time under1 atmO2 supplied continuously by a commonlyusedwater-seal system[18]. A small amount ofmixture was takenout using a syringe. After centrifugation, the mixture was analyzed withan Agilent-6890 gas chromatograph. The identification of products wasdone by GC-MS (Varian Saturn 2100T; injector temperature: 250 C, columntemperature from 80 C to 200 C for β = 7 C/min). The resultingproduct was purified by silica gel column chromatography usingamixedsolvent of n-hexane and ethyl acetate (3:1, v/v) as the eluent. The isolatedproduct was determined by 13C NMR (125 MHz, CDCl3), 1H NMR(500 MHz, CDCl3), GC-MS and FT-IR analysis. Transformation of otherβ-diketones was performed according to the procedure described above.
  • 27
  • [ 18362-64-6 ]
  • [ 24137-06-2 ]
  • 1-allyl-3-isobutyryl-3-isopropyl-1H-benzo[f]indole-2,4,9(3H)-trione [ No CAS ]
  • (4-isobutyryl-5,10-dioxo-5,10-dihydrobenzo[g]quinolin-3-yl)methyl isobutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
15%; 44% With copper diacetate; manganese triacetate; In acetonitrile; at 80℃; General procedure: A mixture of 2-(allylamino)-1,4-naphthoquinone (1; 405 mg, 1.90mmol), pentane-2,4-dione (2a; 772 mg, 7.72 mmol), Cu(OAc)2(463 mg, 2.32 mmol), and Mn(OAc)3 (2.57 g, 9.58 mmol) in MeCN(35 mL) was stirred at 80 C for 5 h [the dark brown color ofMn(OAc)3 disappeared], which was followed by the addition ofpentane-2,4-dione (2a; 779 mg, 7.79 mmol) and Mn(OAc)3 (2.53 g,9.44 mmol). The reaction mixture was stirred for another 3 h. Afterworkup as described as above, the residue was chromatographedover silica gel (40 g, eluted with CH2Cl2-hexane), followed by crystallization(EtOAc-hexane), to give 3a [yield: 28 mg (5%)] and 4a[yield: 307 mg (50%)].
 

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