2-(4-methoxyphenyl)acetonitrile; 4-methoxybenzeneacetonitrile -Drug Synthesis Database

【结构式】

【分子编号】23242

【品名】2-(4-methoxyphenyl)acetonitrile; 4-methoxybenzeneacetonitrile

【CA登记号】104-47-2

【分子式】C₉H₉NO

【分子量】147.1766

【元素组成】C 73.45% H 6.16% N 9.52% O 10.87%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The condensation of cyclohexanone (I) with 4 methoxyphenylacetonitrile (II) by means of n-butyllithium in THF gives 2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl) acetonitrile (III), which is reduced with H2 over Rh/A12O3 in ethanol-ammonia yielding 1-[2-amino-1-(4 methoxyphenyl)ethyl]cyclohexanol (IV). Finally, this compound is methylated with formaldehyde and formic acid in refluxing water.

参考文献中间体

合成目标

【1】 Husbands, G.E.; et al.; Novel phenethylamine antidepressants. 190th ACS Natl Meet (Chicago) 1985, 20, 29-30, Abst MEDI 80.
【2】 Morris, G.E.; Muth, E.A.; Yardley, J.P. (American Home Products Corp.); Phenethylamine derivs.. EP 0112669; ES 8702336; GB 2133788; JP 1991135948; JP 1991178953; US 4535186 .
【3】 Prous, J.; Castaner, J.; WY-45030. Drugs Fut 1988, 13, 9, 839.
【4】 Yardley, J.P.; Husbands, G.E.M.; Stack, G.; et al.; 2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: Synthesis and antidepressant activity. J Med Chem 1990, 33, 10, 2899-905.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(II)	23242	2-(4-methoxyphenyl)acetonitrile; 4-methoxybenzeneacetonitrile	104-47-2	C₉H₉NO	详情	详情
(III)	23243	2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetonitrile		C₁₅H₁₉NO₂	详情	详情
(IV)	23244	1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol	93413-77-5	C₁₅H₂₃NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The target product can be obtained either by condensation of phloroglucinol (I) with carboxylic acid (II) by means of zinc chloride (ZnCl2) and phosphoryl chloride (POCl3) (1) or by reaction of phloroglucinol (I) with acetonitrile derivative (III), boron trifluoride-etherate (BF3-Et2O) and hydrogen chloride in ether.

参考文献中间体

合成目标

【1】 Mohanty, S.; Grover, S.K.; An improved procedure for the acylation on phenols using boron trifluoride-etherate. Curr Sci 1988, 57, 10, 537.
【2】 Devi, N.; et al.; Synthesis of deoxybenzoins. Indian J Chem 1993, 32B, 8, 874.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11799	1,3,5-Benzenetriol; Fluoroglucinol	108-73-6	C₆H₆O₃	详情	详情
(II)	34793	2-(4-methoxyphenyl)acetic acid; p-Methoxyphenyl formate; Homoanisic acid; p-Methyl benzyl formate; 4-methoxyphenylacetic acid; 4-methoxybenzeneacetic acid; p-methoxyphenylacetic acid	104-01-8	C₉H₁₀O₃	详情	详情
(III)	23242	2-(4-methoxyphenyl)acetonitrile; 4-methoxybenzeneacetonitrile	104-47-2	C₉H₉NO	详情	详情

Extended Information