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[ CAS No. 104594-70-9 ] {[proInfo.proName]}

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Chemical Structure| 104594-70-9
Chemical Structure| 104594-70-9
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Product Details of [ 104594-70-9 ]

CAS No. :104594-70-9 MDL No. :MFCD00866470
Formula : C17H16O4 Boiling Point : -
Linear Structure Formula :- InChI Key :SWUARLUWKZWEBQ-VQHVLOKHSA-N
M.W : 284.31 Pubchem ID :5281787
Synonyms :
Caffeic acid phenethyl ester;CAPE;BAF-IN-C09;β-Phenylethyl Caffeate;2-Phenylethyl Caffeate;Caffeic Acid phenylethyl ester;Phenylethyl Caffeate
Chemical Name :Phenethyl 3-(3,4-dihydroxyphenyl)acrylate

Safety of [ 104594-70-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104594-70-9 ]

* 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 [ 104594-70-9 ]

[ 104594-70-9 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 60-12-8 ]
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
  • N,N'-dicyclohexyl-O-(3,4-dihydrocinnamoyl)isourea [ No CAS ]
  • 2
  • [ 331-39-5 ]
  • [ 538-75-0 ]
  • [ 104594-70-9 ]
  • N,N'-dicyclohexyl-O-(3,4-dihydrocinnamoyl)isourea [ No CAS ]
  • 3
  • [ 60-12-8 ]
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
YieldReaction ConditionsOperation in experiment
48% With ytterbium(III) triflate; In nitromethane; at 120℃; for 0.666667h;Catalytic behavior; To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol, 1.0 equiv.),alcohol (5.56 mmol, 1.0 equiv.) in nitromethane (125 mL) was addedytterbium triflate (34.4 mg, 0.056 mmol, 0.01 equiv.). After 5 min inan ultrasonic bath the mixture without protective gas was stirred ona 120 C oil bath for a given time. The reaction mixture was cooled toroom temperature, washed with deionised water (30 mL), 2% NaHCO3(30 mL) and brine, dried over anhydrous Na2SO4 and evaporated underreduced pressure to give the crude product, which was purified on asilica gel column to give the compounds 1-5 and 8-30.2-Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (1): Whitesolid; yield 758 mg, 48.0%; m.p. 128-130 C (lit.20 116-123 C);IR (KBr) numax 3480, 3328, 1683, 1601, 1362, 1301, 1279, 1182 cm-1;1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16 Hz, CH=CHCO),7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz,6-ArH), 6.77 (1H, d, J = 8.0 Hz, 5-ArH), 6.24 (1H, d, J = 16 Hz,CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz,OCH2CH2) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3,145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8,64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found283.0966.
48% With ytterbium(III) triflate; In nitromethane; at 120℃; General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH3NO2 (125 mL) was added Yb(OTf)3 (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2% NaHCO3 (30 mL) and brine, dried over anhydrous Na2SO4, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61% yields. Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (CAPE). White solid (48% yield for esterification reaction); Mp 128-130 C; 1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16.0 Hz, CH=CHCO), 7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz, 5-ArH), 6.77 (1H, d, J = 8.0 Hz, 6-ArH), 6.24 (1H, d, J = 16.0 Hz, CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz, CH2C6H5) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3, 145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8, 64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found 283.0966.
9% With ytterbium(III) triflate; In nitromethane; for 1.5h;Reflux; Caffeic acid (0.5 g, 2.78 mmol) and 2-phenylethanol (0.35 mL,2.78 mmol) were dissolved in nitromethane (62.5 mL). Yb(OTf)3(0.017 g, 0.028 mmol) was added, and the suspension was stirredfor 5 min in an ultrasonic bath followed by an additional 1.5 hstirring under reflux [4]. The reaction mixture was stirred at roomtemperature overnight and washed with NaHCO3-solution (2%,15 mL) and brine (15 mL). The organic phase was dried over Na2SO4and concentrated under reduced pressure. The crude product waspurified by column chromatography (silica gel; chloroform/methanol,99:1), and compound 17 was obtained as a white solid (0.07 g,9%); RF 0.04 (silica gel; chloroform/methanol, 99:1); m.p.128-130 C (lit.: [19]: 126-128 C); IR (KBr): nu 3480s, 1685m,1636m, 1602s, 1535w, 1442w, 1363w, 1302m, 1279s, 1182s cm1;UV-vis (CHCl3): lambda (log epsilon) 250 (4.06), 320 (4.21), 353 (4.28) nm; 1HNMR (500 MHz, CDCl3): delta 7.56 (d, J 15.9 Hz, 1H, 3-H), 7.34-7.30(m, 2H, 2-H), 7.27-7.22 (m, 3H, 3-H4-H), 7.07 (d, J 2.0 Hz, 1H, 50-H), 7.01 (dd, J 8.2, 2.0 Hz, 1H, 20-H), 6.87 (d, J 8.2 Hz, 1H, 60-H),6.25 (d, J 15.9 Hz, 1H, 2-H), 4.42 (t, J 7.1 Hz, 2H, 1-H), 3.01 (t,J 7.1 Hz, 2H, 2-H); 13C NMR (125 MHz, CDCl3): delta 167.8 (C-1),146.5 (C-40), 145.2 (C-30), 143.9 (C-3), 138.0 (C-1), 129.1 (C-3), 128.7(C-2), 127.7 (C-10), 126.8 (C-4), 122.7 (C-60), 115.7 (C-2), 115.6 (C-50),144.6 (C-20), 65.3 (C-1), 35.4 (C-2) ppm; MS (ESI, MeOH): m/z(%) 285.0 ([MH], 45), 302.2 ([MNH4], 23), 307.1 ([MNa],100), 446.1 ([3 MKH]2, 44), 580.1 ([4 MNaH]2, 23), 588.0([4MKH]2, 50), 590.8 ([2MNa], 42), 599.9 ([4MZn]2, 48);analysis calcd for C17H16O4 (284.31): C 71.82, H 5.67; found: C 71.69,H 5.83.
With toluene-4-sulfonic acid; In benzene; Synthesis of Cinnamic Acid Analogues. The synthesis of cinnamic acid analogues was achieved by straight forward application of literature techniques. Two general approaches, designated "method A" and "method B" were utilized: Method A: Synthesis of Caffeic acid beta-phenylethyl ester (CAPE, 67H-42-A). A solution of 1.80 g (10.0 mmol) of caffeic acid, 17.9 mL (150 mmol) of beta-phenylethyl alcohol and 100 mg of p-toluenesulfonic acid in benzene (100 mL) were stirred overnight at reflux with a Dean Stark trap. Solvent and excess alcohol were removed by distillation and residue purified by silica gel chromatography (petroleum ether/CHCl3). Product was crystallized (ether/petroleum ether) to provide 67H-42-A as snow-white crystals, 1.0 g (35%): mp 128.0 C. 126-128 C.) (Grunberger, D. et al., Experimentia, (1988) 44:230-2).
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 48h; General procedure: Cinnamicacid esters (13-22) were synthesized according to a modified previous procedure.31) To a mixture of cinnamic acid derivatives (Ia-d, 3.0 mmol) and the appropriate alcohol (2.0 mmol)in dry tetrahydrofuran (6mL) were added triphenylphosphine (3.0 mmol) and diisopropyl azodicarboxylate (DIAD(3.0mmol). The reaction mixture was stirred for 48h at room temperature and the whole mixture was extracted with AcOEt and saturated NaHCO3 solution, and the organic extract was washed with brine.The organic layer was dried overNa2SO4 and the solvent was evaporated under reduced pressure. The residue was then purified by silica gel column chromatography (hexane:AcOEt=2:1)to give the title compound.

  • 4
  • [ 104594-70-9 ]
  • 2-phenylethyl 3-(3,4-dihydroxyphenyl)propanoate [ No CAS ]
  • 5
  • [ 331-39-5 ]
  • [ 103-63-9 ]
  • [ 104594-70-9 ]
YieldReaction ConditionsOperation in experiment
67% General procedure: To a stirredsolution of the acid (1 mmol) in dry hexamethyl phosphoramide (5 mL), Nua2CO3 (126 mg, 1.19 mmol) wasadded and stirring continued for 30 min. At the end of this period, thecorresponding bromide (1.14 mmol) was added to the reaction mixture followed bya catalytic amount of potassium iodide. The mixture was stirred at room temperaturefor 48 h, after which EtOAc (30 ml) and HCl 0.5 N (5 mL) were added. Theorganic phase was washed with brine, dried over Na2SO4,filtered and concentrated under reduced pressure. The crude product waspurified by column chromatography.
  • 7
  • [ 139-85-5 ]
  • [ 848598-50-5 ]
  • [ 104594-70-9 ]
YieldReaction ConditionsOperation in experiment
With piperidine; pyridine; at 20℃; General procedure: The Meldrum?s acid (3.6g, 25mmol) was added into toluene (50ml), then added alcohol or phenol (25mmol). The mixture was heated and refluxed for 5 hrs. When the mixture was cooled to room temperature, added substituted benzaldehyde (10mmol), pyridine (2.5ml) and piperidine (0.25ml). The stirring continued at room temperature, using TLC to trace the reaction until the reaction completely finished. The solvents were distilled out in vacuum; the residue was dissolved in diethyl ether (about 30ml), washed with saturated solution of sodium bicarbonate two times (20ml×2), then diluted hydrochloride acid and distilled water, respectively. The ether phase was driedby anhydrous MgSO4 overnight. After removal of the drier, the solvent was distilled out to get crude solid. (If the crude product was oil, dissolved in dichloromethane (10ml) and then was subjected to chromatograph on a silica gel column (15 g), eluted with ethyl acetate and petroleum ether 1:15. The eluted fraction was distilled outto get crude product. ) The crude solid was recrystallized from a mixture of benzene and diethyl ether (8:2) to afford pure product.
270 g With piperidine; In pyridine; toluene; at 95℃; for 15h; Add 1L of toluene to the 3L reaction flask,SM1 (cyclopropane (isopropyl) isopropyl ester, 240 g, commercially available) was added in succession under mechanical stirringAnd SM2 (phenylethanol, 202 g, commercially available),After the addition,Warm up to 100C to start timingStop the reaction after 8 hoursCool naturally to cool down to room temperatureSM3 (3,4-dihydroxybenzaldehyde, 160 g, commercially available) was added while stirring was continued.Then add pyridine 166ml and piperidine 17ml,Then it warms up to an internal temperature of 95C.The reaction was stopped after 15 hours of reaction.Cool down to room temperatureAfter adding 1 L of ethyl acetate, the organic phase was washed successively with 1 L of 1M hydrochloric acid solution and 1 L of saturated saline, and the organic phase was dried over anhydrous sodium sulfate for 30 minutes, filtered, and the organic solvent was evaporated in vacuo to obtain a crude product. 2L n-hexane was filtered after beatingThe cake was vacuum dried in a box at 40C for 24 hours to give 270 g of a product of caffeic acid phenylethyl ester.
General procedure: The desired amount of malonic acid mono esters (0.6 mmol, 1.2 equiv.) was dissolved in toluene (1 mL) followed by the addition of pyridine (12.5 mmol, 25 equiv., 1 mL) and piperidine (0.80 mmol, 1.6 equiv., 79 muL). This mixture was stirred at r.t. for 10 min to form enolates before the desired aldehyde (0.5 mmol,1.0 equiv.) was added at 0C. The reaction mixture was continued to bestirred at r.t. for 1?6 days. TLC was used to monitor the reaction progress. Once the reaction was complete, the reaction mixture was transferred to a separatory funnel using EtOAc (15 mL) and washed with 5% HCl (10 mL×2) and distilled water (10 mL×2). After removalof the ethyl acetate by rotatory evaporation, the crude product was purified by automated flash chromatography, eluting with an ethylacetate/hexanes or methanol/methylene chloride gradient to afford the desired products.
  • 8
  • [ 104594-70-9 ]
  • C17H15O4 [ No CAS ]
  • C17H14O4(1-) [ No CAS ]
  • 10
  • [ 92778-42-2 ]
  • [ 104594-70-9 ]
  • 12
  • C30H24O3 [ No CAS ]
  • [ 104594-70-9 ]
  • 14
  • [ 118971-54-3 ]
  • [ 104594-70-9 ]
YieldReaction ConditionsOperation in experiment
75% With pyrrolidine; In tetrahydrofuran; at 20℃; for 0.5h; To a solution of (E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate 11a (474 mg, 1.29 mmol, 1 eq) in anhydrous THF (15 mL) was added pyrrolidine (cat). After stirring at room temperature for 30 min, water (10 mL) was added and the reaction mixture was extracted with EtOAc (20 mL). The combined organic layers were washed with 1 N HCl (7 * 20 mL), brine. After drying (Na2SO4) and concentration under reduced pressure, CAPE 3 was obtained as a yellow powder (36.7 mg, 75%). Mp 125.5 C. Rf = 0.75 (SiO2, 40% EtOAc/cyclohexane). 1H NMR (400 MHz, Acetone-d6) delta 8.36 (br s, 1H), 8.08 (br s, 1H), 7.6 (d, J = 15.0 Hz, 1H) 7.40 (dd, J = 9.0, 2.0 Hz, 1H), 7.35-7.28 (m, 5H), 7.25 (d, J = 2.0 Hz, 1H), 7.20 (d, J = 9.0 Hz, 1H), 6.30 (d, J = 15.0 Hz, 1H), 4.35 (t, J = 7.0 Hz, 2H), 2.90 (t, J = 7.0 Hz, 2H). 13C NMR (101 MHz, Acetone-d6) delta 167.4, 148.9, 148.4, 145.9, 139.4, 129.9, 129.4, 127.7, 127.3, 122.6, 116.5, 115.6, 115.3, 65.4, 35.9.
  • 15
  • [ 88623-81-8 ]
  • [ 104594-70-9 ]
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