(+/-)-3-(acetoxymethyl)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]benzonitrile | 674806-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-3-(acetoxymethyl)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]benzonitrile
• 英文别名: monoacetyl cyanodiol ester；4-(4-dimethylamino)-1-(4'-fluorophenyl)-1-(hydroxybutyl)-3-(acetoxymethyl)benzonitrile；3-[(Acetyloxy)methyl]-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-benzonitrile；[5-cyano-2-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]phenyl]methyl acetate
• CAS: 674806-15-6
• 化学式: C₂₂H₂₅FN₂O₃
• 分子量: 384.451
• InChiKey: PYYMVUJDWUKYPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁二酸 、 (+/-)-3-(acetoxymethyl)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]benzonitrile 以 丙酮 为溶剂， 以4 g的产率得到monoacetyl cyanodiol ester succinate
  参考文献：
  名称：

  [EN] NOVEL RECOVERY AND RECYCLING PROCESS OF RACEMIC 4-(4-DIMETHYLAMINO)-1-(4'-FLUOROPHENYL)-1-(HYDROXYBUTYL)-3-(HYDROXYMETHYL)-BENZONITRILE
  [FR] NOUVEAU PROCÉDÉ DE RÉCUPÉRATION ET DE RECYCLAGE DE 4- (4-DIMÉTHYLAMINO)-1-(4 '-FLUOROPHÉNYL)-1-(HYDROXYBUTYL)-3-(HYDROXYMÉTHYL)-BENZONITRILE RACÉMIQUE

  摘要：

  本文披露了一种新颖的对消旋4-(4-二甲氨基)-1-(4'-氟苯基)-1-(羟丁基)-3-(羟甲基)-苯甲腈（以下简称为氰二醇）的回收和循环利用过程。消旋氰二醇是一种中间体，用于制备西酞普兰、艾司西酞普兰或其药用可接受的盐。

  公开号：

  WO2017009866A1
• 作为产物：
  描述：

  乙酸酐 、 4-(4-二甲胺基-1-对氟苯基-1-羟基丁基)-3-(羟甲基)苯腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到(+/-)-3-(acetoxymethyl)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]benzonitrile
  参考文献：
  名称：

  Enzymatic resolution of a quaternary stereogenic centre as the key step in the synthesis of (S)-(+)-citalopram

  摘要：

  The enzymatic resolution of 4-[(4-dimethylamino)-1-(4'-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile, a useful intermediate in the synthesis of enantionterically pure citalopram, has been studied. Candida antarelica lipase B (CAL-B) catalyzes the enzymatic acetylation of the primary benzylic alcohol with high en anti oselectivity at the quaternary stereogenic centre. The enzymatic en anti oselective hydrolysis of the 3-acetyloxymethyl derivative catalyzed by CAL-B is also possible. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.022

文献信息

• Chemo-enzymatic process for the preparation of escitalopram
  申请人：Cotticelli Giovanni

  公开号：US20070238887A1

  公开（公告）日：2007-10-11

  A process for preparing an intermediate for synthesizing escitalopram and the pharmaceutically acceptable salts thereof from 4-(4-dimethylamino)-1-(4′-fluorophenyl)-1-(hydroxybutyl)-3-(acyloxymethyl) benzonitrile is described. The process involves converting said intermediate into the (S+) enantiomer of citalopram by means of enzymatic enantiomeric resolution.

  本发明描述了一种制备用于合成艾司西酞普兰及其药物可接受的盐的中间体的方法，所述中间体为4-(4-二甲氨基)-1-(4'-氟苯基)-1-(羟丁基)-3-(酰氧甲基)苯甲腈。该方法涉及通过酶对映体分辨将所述中间体转化为(S+)环舒尼普兰对映体。
• US7470526B2
  申请人：——

  公开号：US7470526B2

  公开（公告）日：2008-12-30
• [EN] NOVEL RECOVERY AND RECYCLING PROCESS OF RACEMIC 4-(4-DIMETHYLAMINO)-1-(4'-FLUOROPHENYL)-1-(HYDROXYBUTYL)-3-(HYDROXYMETHYL)-BENZONITRILE<br/>[FR] NOUVEAU PROCÉDÉ DE RÉCUPÉRATION ET DE RECYCLAGE DE 4- (4-DIMÉTHYLAMINO)-1-(4 '-FLUOROPHÉNYL)-1-(HYDROXYBUTYL)-3-(HYDROXYMÉTHYL)-BENZONITRILE RACÉMIQUE
  申请人：IPCA LABORATORIES LTD

  公开号：WO2017009866A1

  公开（公告）日：2017-01-19

  Disclosed herein is a novel recovery and recycling process of racemic 4-(4- dimethylamino)-1-(4'-fluorophenyl)-1-(hydroxybutyl)-3-(hydroxymethyl)- benzonitrile (hereinafter referred as cyanodiol). The racemic cyanodiol is an intermediate useful for preparation of Citalopram, Escitalopram or pharmaceutically acceptable salts thereof.

  本文披露了一种新颖的对消旋4-(4-二甲氨基)-1-(4'-氟苯基)-1-(羟丁基)-3-(羟甲基)-苯甲腈（以下简称为氰二醇）的回收和循环利用过程。消旋氰二醇是一种中间体，用于制备西酞普兰、艾司西酞普兰或其药用可接受的盐。
• Enzymatic resolution of a quaternary stereogenic centre as the key step in the synthesis of (S)-(+)-citalopram
  作者：Laura F. Solares、Rosario Brieva、Margarita Quirós、Isidro Llorente、Miguel Bayod、Vicente Gotor

  DOI：10.1016/j.tetasy.2003.10.022

  日期：2004.1

  The enzymatic resolution of 4-[(4-dimethylamino)-1-(4'-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile, a useful intermediate in the synthesis of enantionterically pure citalopram, has been studied. Candida antarelica lipase B (CAL-B) catalyzes the enzymatic acetylation of the primary benzylic alcohol with high en anti oselectivity at the quaternary stereogenic centre. The enzymatic en anti oselective hydrolysis of the 3-acetyloxymethyl derivative catalyzed by CAL-B is also possible. (C) 2003 Elsevier Ltd. All rights reserved.