rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol | 521059-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol
• 英文别名: (RS)-1-[2-dimetylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol；rac-sila-venlafaxine；(RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol；Silacyclohexan-1-ol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-；2-(1-hydroxysilinan-1-yl)-2-(4-methoxyphenyl)-N,N-dimethylethanamine
• CAS: 521059-17-6
• 化学式: C₁₆H₂₇NO₂Si
• 分子量: 293.481
• InChiKey: KIXBFSFRCBHKLN-UHFFFAOYSA-N

物化性质

• 熔点：
  33 °C
• 沸点：
  409.5±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol 生成 (R)-Sila-venlafaxine hydrochloride
  参考文献：
  名称：

  (R)-Sila-venlafaxine: A selective noradrenaline reuptake inhibitor for the treatment of emesis

  摘要：

  Sila-substitution of drugs (the carbon/silicon switch) is a concept that is being successfully used for the development of new chemical entities. The (R)-sila-analogue of the antidepressant venlafaxine is devoid of the serotonin reuptake inhibition observed with the marketed drug, leading to a selective noradrenaline reuptake inhibitor displaying anti-emetic properties. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.062
• 作为产物：
  描述：

  1,1-二氯硅杂环己烷 在 盐酸 、 正丁基锂 、 四甲基乙二胺 、 2,4,6-triisopropylbenzenesulfonylhydrazone 、 potassium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 112.67h， 生成 rac-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol
  参考文献：
  名称：

  (R)-Sila-venlafaxine: A selective noradrenaline reuptake inhibitor for the treatment of emesis

  摘要：

  Sila-substitution of drugs (the carbon/silicon switch) is a concept that is being successfully used for the development of new chemical entities. The (R)-sila-analogue of the antidepressant venlafaxine is devoid of the serotonin reuptake inhibition observed with the marketed drug, leading to a selective noradrenaline reuptake inhibitor displaying anti-emetic properties. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.062

文献信息

• [EN] 1-(2-AMINO-1-PHENYL-ETHYL) 1- SILACYCLOHEXAN-1- OL DERIVATIVES AND USE THEREOF IN THE PREPARATION OF A MEDICAMENT<br/>[FR] DERIVES DE 1-(2-AMINO-1-PHENYL-ETHYL)-SILACYCLOHEXAN-1-OL ET UTILISATION DESDITS DERIVES POUR PREPARER UN MEDICAMENT
  申请人：AMEDIS PHARM LTD

  公开号：WO2004094436A1

  公开（公告）日：2004-11-04

  A compound selected from: (RS)-1-[2-methylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol; (R)-1-[2-methylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol; (S)-1-[2-methylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol; (RS)-1-[2-amino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol; (R)-1-[2-amino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol (S)-1-[2-amino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1-ol; (RS)-1-[2-dimethylamino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (R)-1-[2-dimethylamino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (S)-1-[2-dimethylamino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (RS)- 1-[2-amino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (R)-1-[2-amino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (S)-1-[2-amino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (RS)- 1-[2-methylamino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (R)-1-[2-methylamino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (S)-1-[2-methylamino-1-(4-hydroxyphenyl)ethyl]-1-silacyclohexan-1-ol; (RS)-1-[2-dimethyl amino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1,4-diol; (R)-1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-l,4-diol; and (S)-1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]-1-silacyclohexan-1,4-diol; or a pharmaceutically acceptable salt thereof or a prodrug form that is hydrolysable to a compound as defined above.

  从中选择的化合物：(RS)-1-[2-甲氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1-醇；(R)-1-[2-甲氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1-醇；(S)-1-[2-甲氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1-醇；(RS)-1-[2-氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1-醇；(R)-1-[2-氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1-醇；(S)-1-[2-氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1-醇；(RS)-1-[2-二甲基氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(R)-1-[2-二甲基氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(S)-1-[2-二甲基氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(RS)-1-[2-氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(R)-1-[2-氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(S)-1-[2-氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(RS)-1-[2-甲氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(R)-1-[2-甲氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(S)-1-[2-甲氨基-1-(4-羟基苯基)乙基]-1-硅环己烷-1-醇；(RS)-1-[2-二甲基氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1,4-二醇；(R)-1-[2-二甲基氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1,4-二醇；以及(S)-1-[2-二甲基氨基-1-(4-甲氧基苯基)乙基]-1-硅环己烷-1,4-二醇；或其药学上可接受的盐或可水解为上述定义的化合物的前药形式。
• (R)-Sila-venlafaxine: A selective noradrenaline reuptake inhibitor for the treatment of emesis
  作者：Graham A. Showell、Matthew J. Barnes、Jürgen O. Daiss、John S. Mills、John G. Montana、Reinhold Tacke、Julie B.H. Warneck

  DOI：10.1016/j.bmcl.2005.12.062

  日期：2006.5

  Sila-substitution of drugs (the carbon/silicon switch) is a concept that is being successfully used for the development of new chemical entities. The (R)-sila-analogue of the antidepressant venlafaxine is devoid of the serotonin reuptake inhibition observed with the marketed drug, leading to a selective noradrenaline reuptake inhibitor displaying anti-emetic properties. (C) 2006 Elsevier Ltd. All rights reserved.