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[ CAS No. 428855-17-8 ] {[proInfo.proName]}

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Chemical Structure| 428855-17-8
Chemical Structure| 428855-17-8
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Product Details of [ 428855-17-8 ]

CAS No. :428855-17-8 MDL No. :MFCD07367843
Formula : C18H21NO Boiling Point : No data available
Linear Structure Formula :- InChI Key :QILKRCMMHALAJX-UHFFFAOYSA-N
M.W : 267.37 Pubchem ID :15514370
Synonyms :

Safety of [ 428855-17-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 428855-17-8 ]

* 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 [ 428855-17-8 ]

[ 428855-17-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 77385-90-1 ]
  • [ 925-90-6 ]
  • [ 428855-17-8 ]
YieldReaction ConditionsOperation in experiment
84.3% With titanium(IV) isopropylate; In tetrahydrofuran; at 10℃;Inert atmosphere; Under an atmosphere of nitrogen, 2- (dibenzylamino) acetate (IV-1) (2.0 g, 7.0 mmol) was dissolved in tetrahydrofuran (10 ml)Tetraisopropyl titanate (0.5 g, 1.7 mmol) was added,A solution of 1M ethylmagnesium bromide in tetrahydrofuran (21 ml, 21.0 mmol) was added at 10 C,Plus,Continue stirring.TLC monitoring reaction end,Saturated ammonium chloride solution quenched,Solid precipitation.filter,The filter cake was washed with ethyl acetate (50 ml x 2)The combined organic layers were washed with saturated sodium bicarbonate solution (50 ml)The organic layer was dried over anhydrous sodium sulfate,filter,Concentrated crude,Purification by flash column chromatography (petroleum ether: ethyl acetate = 5: 1)Get the oil,A total of 1.59g,The yield was 84.3%.
60% Step 2: Preparation of 1-((diphenylmethylamino)methyl)cyclopropan-1-ol Titanium isopropoxide (622 mg, 2.33 mmol) was added to a solution of ethyl N-(phenylmethylene)glycinate (3.0 g, 11 mmol) in diethyl ether (100 mL) at room temperature. Ethylmagnesium bromide (3.0 M Et2O solution, 10.6 mL, 31.8 mmol) was added dropwise and slowly, and the mixture was stirred for 12 hours at room temperature. After the reaction was cooled to 0C, hydrochloric acid (2M, 10mL) was added slowly, then the reaction was warmed up to room temperature slowly and stirred for 30 minutes. After addition of saturated NaHCO3 aqueous solution (60 mL), the reaction solution was stirred for 10 minutes, extracted twice with CH2Cl2, and concentrated. The resulting residue was subjected to column chromatography to obtain the title compound 1-((diphenylmethylamino)methyl)cyclopropan-1-ol (1.7 g, 60%). MS m/z (ESI): 268.2 [M+H]+.
2.05 g In tetrahydrofuran; at 0 - 35℃; for 16h;Inert atmosphere; Under a nitrogen atmosphere, a 3.0 M solution of ethylmagnesium bromide in THF (9.41 mL) was added dropwise to a solution of ethyl 2-(dibenzylamino)acetate (4.0 g) and tetraisopropyl titanate (827 μL) in THF (50 mL) at 0 C., and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.05 g) as a pale-yellow oil. (0864) 1H NMR (400 MHz, DMSO-d6) δ 0.26-0.38 (2H, m), 0.49-0.60 (2H, m), 2.53 (2H, s), 3.67 (4H, s), 5.01 (1H, s), 7.17-7.25 (2H, m), 7.31 (4H, t, J=7.5 Hz), 7.35-7.46 (4H, m).
6.59 g With titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; at 0 - 35℃;Inert atmosphere; (A) 1-((Dibenzylamino)methyl)cyclopropanol To a mixture of ethyl 2-(dibenzylamino)acetate (11.2 g), titanium tetraisopropoxide (2.398 mL) and THF (130 mL), a 3 M solution of ethyl magnesium bromide in diethyl ether (26.4 mL) was added dropwise at 0 C., and the resulting mixture was stirred overnight under nitrogen atmosphere at room temperature. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (6.59 g). 1H NMR (300 MHz, DMSO-d6) δ 0.19-0.39 (2H, m), 0.46-0.63 (2H, m), 2.53 (2H, s), 3.66 (4H, s), 5.04 (1H, s), 7.16-7.26 (2H, m), 7.27-7.35 (4H, m), 7.36-7.43 (4H, m).
With titanium(IV) isopropylate; In diethyl ether; at 0 - 20℃; for 24h; Ethyl dibenzyl glycinate (1 g, 3.5 mmol, 1.0 equiv) was dissolved in diethyl ether (10 mL) and cooled to 0 C. Ti(OiPr)4 (0.25 g, 0.88 mmol, 0.25 equiv) and EtMgBr (3.0 M in diethyl ether) (4.7 mL, 14.1 mmol, 4.0 equiv) were added, and the reaction mixture was stirred at RT for 24 h. The reaction mixture was cooled to 0 C., quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (5% EtOAc/hexane) to afford I-58A. LCMS (m/z): 268.3 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 7.39 (d, J=7.0 Hz, 4H), 7.32 (t, J=7.5 Hz, 4H), 7.23 (t, J=7.2 Hz, 2H), 5.06 (s, 1H), 3.64 (d, J=20.7 Hz, 4H), 2.53 (s, 2H), 0.57-0.54 (m, 2H), 0.33 (dd, J=6.7, 4.6 Hz, 2H).

  • 2
  • [ 428855-17-8 ]
  • 1-(aminomethyl)cyclopropan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 50℃; under 2585.81 Torr; for 12h; To a mixture of compound 32a (300 mg, 1.1mmol) , Pd/C (150 mg, 10%palladium on carbon wetted with 55%water) and MeOH (5 mL) was added acetic acid (1 mL) . The mixture was hydrogenated at 50 for 12 hrs under H2(50 psi) . The mixture was filtered and the filtrate was concentrated to dryness to afford the crude title product as colorless oil (97.6 mg, 100%yield) .1H NMR (CDCl3, 400 MHz) : δ 2.84 (s, 2H) , 0.77 -0.59 (m, 2H) , 0.55-0.54 (m, 2H) .
  • 3
  • [ 428855-17-8 ]
  • 1-((benzylamino)methyl)cyclopropan-1-ol [ No CAS ]
  • 4
  • [ 428855-17-8 ]
  • N,N-dibenzyl-1-(1-fluorocyclopropyl)methanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.38 g With diethylamino-sulfur trifluoride; In toluene; at 10 - 35℃;Inert atmosphere; (B) N,N-Dibenzyl-1-(1-fluorocyclopropyl)methanamine To a mixture of <strong>[428855-17-8]1-((dibenzylamino)methyl)cyclopropanol</strong> (6.59 g) and toluene (130 mL), DAST (7.16 mL) was added at room temperature, and the resulting mixture was stirred overnight under nitrogen atmosphere at the same temperature. Saturated aqueous sodium hydroxide solution was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (5.38 g). MS: [M+H]+270.0.
5.38 g With diethylamino-sulfur trifluoride; In toluene; at 20℃;Inert atmosphere; At room temperature,In 1 - ((dibenzylamino) methyl) cyclopropanol (6.59 g)And toluene (130 mL)Of the mixture was added DAST (7.16 mL)The resulting mixture was stirred overnight at room temperature under nitrogen atmosphere.A saturated aqueous solution of sodium hydroxide was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate.The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure.The residue was purified by silica gel column chromatography (ethyl acetate / hexane) to give the title compound (5.38 g).
  • 5
  • [ 103-49-1 ]
  • [ 428855-17-8 ]
  • 6
  • [ 100-44-7 ]
  • [ 428855-17-8 ]
  • 7
  • [ 3167-63-3 ]
  • [ 428855-17-8 ]
  • diethyl ({1-[(dibenzylamino)methyl]cyclopropoxy}methyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere; Under nitrogen protection,A solution of 1- (dibenzylamino) methylcyclopropanol (II-1) (2.3 g, 8.6 mmol) in dimethylformamide (20 ml)Potassium carbonate (1.18 g, 8.6 mmol) and diethyl alpha-chloromethylphosphonate (III-2) (1.68 g, 9.03 mmol) were added,The temperature was raised to 60 C.TLC monitoring reaction end,The solvent was distilled off under reduced pressure,Add water (20 ml)Extracted with ethyl acetate (10 ml x 2)Combined organic layer,Dried over anhydrous sodium sulfate,filter,Concentrated crude,Purification by flash column chromatography (petroleum ether: ethyl acetate = 2: 1)Get the oil,A total of 3.05g,The yield was 85%.
  • 8
  • [ 31618-90-3 ]
  • [ 428855-17-8 ]
  • diethyl ({1-[(dibenzylamino)methyl]cyclopropoxy}methyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.5% With lithium tert-butoxide; In tetrahydrofuran; at 60℃;Inert atmosphere; Under nitrogen protection,A solution of 1- (dibenzylamino) methylcyclopropanol (II-1) (1.15 g, 4.3 mmol) in tetrahydrofuran (10 ml)Lithium tert-butoxide (0.5 g, 6.2 mmol) and diethyl p-toluenesulfonyloxymethylphosphonate (III-1) (2.0 g, 6.2 mmol)The temperature was raised to 60 C.TLC monitoring reaction end,After cooling to room temperature, add saturated ammonium chloride solution (10ml)Solid precipitation.filter,The filter cake was washed with ethyl acetate (10 ml x 2)The combined organic layers were dried over anhydrous sodium sulfate,filter,Concentrated crude,Purification by flash column chromatography (petroleum ether: ethyl acetate = 2: 1)Get the oil,A total of 1.57g,The yield was 87.5%;
  • 9
  • [ 77385-90-1 ]
  • [ 428855-17-8 ]
YieldReaction ConditionsOperation in experiment
6.59 g With titanium(IV) isopropylate; methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 - 20℃;Inert atmosphere; At 0 C.To a solution of ethyl 2- (dibenzylamino) acetate (11.2 g)Titanium tetraisopropoxide (2.398 mL) and THF (130 mL)The mixture is added dropwiseEthyl magnesium bromide in diethyl etherSolution (26.4 mL),The resulting mixture was stirred in a nitrogen atmosphere,Stir at room temperature overnight.A saturated aqueous solution of ammonium chloride was added to the reaction mixture,And the aqueous layer was extracted with ethyl acetate.The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure.The residue was purified by silica gel column chromatography (ethyl acetate / hexane) to give the title compound (6.59 g).
  • 10
  • [ 428855-17-8 ]
  • [ 74-88-4 ]
  • N,N-dibenzylmethyl-1-(1-methoxycyclopropyl)methylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% Step 3: Preparation of N,N-dibenzylmethyl-1-(1-methoxycyclopropyl)methylamine NaH (60% in oil, 179 mg, 4.5 mmol) was added in batches to a solution of 1-((diphenylmethylamino)methyl)cyclopropan-1-ol (1.0 g, 3.7 mmol) in DMF (100 mL) in an ice bath. The mixture was stirred at this temperature for 60 minutes, followed by addition of methyl iodide (584 mg, 4.1 mmol), then warmed up to room temperature slowly and stirred for 2 hours. After addition of saturated NH4Cl aqueous solution (10 mL), the reaction solution was concentrated. The resulting residue was dissolved in CH2Cl2, washed with saturated NH4Cl aqueous solution and saturated brine successively, dried over anhydrous sodium sulfate, and concentrated. The resulting residue was subjected to column chromatography to obtain the title compound N,N-dibenzylmethyl-1-(1-methoxycyclopropyl)methylamine (350 mg, 33%). MS m/z (ESI): 282.2 [M+H]+.
14.1% To a stirred solution of 1-[(dibenzylamino)methyl]cyclopropan-1-ol (13.5 g, 50.5 mmol) in dry THF (200 mL) at 0C under Ar was added portionwise sodium hydride (3.03 g, 126mmol). The mixture was stirred for lh then iodomethane (10.8 g, 75.7 mmol, 4.71 mL) was added dropwise at 0C. The reaction mixture was stirred at r.t. overnight and carefully poured into brine (200 mL). The mixture was extracted with EtOAc (2 x 100 mL), the combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica with hexane-MTBE (40:1) as an eluent to afforddibenzyl[(1-methoxycyclopropyl)methyl]amine (2.0 g, 7.11 mmol, 14.1% yield) as a yellow oil.
With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20℃; for 3h; I-58A (2 g, 7.5 mmol, 1.0 equiv) was dissolved in THF (20 mL) and cooled to 0 C. NaH (60% suspension in mineral oil, 0.34 g, 8.98 mmol, 1.2 equiv) and iodomethane (1.6 g, 11.2 mmol, 1.5 equiv) were added, and the reaction mixture was stirred at RT for 3 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (3% EtOAc/hexane) to afford the title compound. LCMS (m/z): 282.2 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 7.31 (ddd, J=37.8, 14.1, 7.0 Hz, 10H), 3.63 (s, 4H), 3.13 (s, 3H), 2.56 (s, 2H), 0.68 (s, 2H), 0.39 (q, J=5.1 Hz, 2H).
  • 11
  • [ 100-39-0 ]
  • [ 428855-17-8 ]
  • 12
  • [ 94226-55-8 ]
  • [ 925-90-6 ]
  • [ 428855-17-8 ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate; magnesium; In diethyl ether; at 15 - 20℃;Inert atmosphere; To a solution of methyl 2-(dibenzylamino)acetate (20.0 g, 74.3 mmol) in dry diethyl ether (250 ml) under a stream of argon was added dropwise a solution of titanium tetraisopropoxide (5.28 g, 18.6 mmol, 5.5 mL) in diethyl ether (50 mL). Ethylmagnesium bromide in diethyl ether (1M solution freshly prepared from bromoethane (24.3 g, 222 mmol,16.6 mL) and magnesium (5.69 g, 234 mmol) was added dropwise at 15-20C under Ar. The reaction mixture was stirred overnight, then cooled to 0C and quenched by dropwise addition of sat. aq. NH4C1 solution (300 mL). The reaction mixture was stirred at r.t. for 2 h and filtered. The organic phase was separated and the aqueous phase was extracted with MTBE (100 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford crude 1-[(diben.zylamino)methyl]cyclopropan-1-ol (17.5 g, 50.0% purity, 32.73 mmol, 44% yield) as yellow oil, that was used in the next step without purification.
  • 13
  • [ 79-44-7 ]
  • [ 428855-17-8 ]
  • 1-((dibenzylamino)methyl)cyclopropyl dimethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20℃; for 5h; I-58A (5 g, 18.7 mmol, 1.0 equiv) was dissolved in THF (50 mL) and cooled to 0 C. NaH (60% suspension in mineral oil, 0.93 g, 24.3 mmol, 1.3 equiv) and dimethyl carbamic chloride (3 g, 28.1 mmol, 1.5 equiv) were added, and the reaction mixture was stirred at RT for 5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride and was extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (10% EtOAc/Hexane) to afford I-58B. The product was used without further purification. LCMS (m/z): 339.4 [M+H]. 1H NMR (400 MHz, DMSO-d6) δ 7.39-7.25 (m, 10H), 3.64 (d, J=15.8 Hz, 4H), 2.83 (d, J=28.9 Hz, 6H), 2.71 (d, J=22.3 Hz, 2H), 0.81-0.74 (m, 2H), 0.63 (dd, J=7.6, 5.7 Hz, 2H).
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