methanesulfonic acid (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl ester | 367922-41-6

• 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: methanesulfonic acid (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl ester
• 英文别名: (S)-3,5-bis(trifluoromethyl)benzylmesylate；[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl] methanesulfonate
• CAS: 367922-41-6
• 化学式: C₁₁H₁₀F₆O₃S
• 分子量: 336.255
• InChiKey: WDTALWFHDQEXJL-LURJTMIESA-N

物化性质

• 沸点：
  298.8±40.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲胺 、 methanesulfonic acid (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl ester 以 水 、 甲苯 为溶剂， 70.0 ℃ 、200.0 kPa 条件下， 反应 24.0h， 生成 (S)-N-甲基-1-[3,5-二(三氟甲基)苯基]乙胺
  参考文献：
  名称：

  WO2006/67395

  摘要：

  公开号：
• 作为产物：
  描述：

  (S)-1-[3,5-二(三氟甲基)苯基]乙醇 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到methanesulfonic acid (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl ester
  参考文献：
  名称：

  Stereoselective Preparation of a Cyclopentane-Based NK1 Receptor Antagonist Bearing an Unsymmetrically Substituted Sec−Sec Ether

  摘要：

  A highly efficient synthesis of the potent and selective NK-1 receptor antagonist 1 is described. The key transformation involved the etherification reaction between cyclopentanol 12 and chiral imidate 30 which was catalyzed by HBF4 to initially give ether 14 as a 17:1 mixture of diastereomers and in 75% combined yield. The diastereoselectivity was upgraded to 109:1 by crystallization of the triethylamine solvate 44 which was isolated in 54% yield from 12. Mechanistic studies confirmed that the etherification reaction proceeds through an unprecedented S(N)2 reaction pathway under typical S(N)1 reaction conditions.

  DOI：

  10.1021/jo061268x

文献信息

• Process
  申请人：Hodges George Robert

  公开号：US20100029985A1

  公开（公告）日：2010-02-04

  A process for the preparation of a compound of Formula (1) wherein Ar represents an optionally substituted hydrocarbyl or an optionally substituted heterocyclyl group comprising an aromatic moiety; and R 1 and R 2 each independently represent an optionally substituted hydrocarbyl or an optionally substituted heterocyclyl group; said process comprising: a) reducing a compound of Formula (2) to form a compound of Formula (3): b) activating the compound of Formula (3) to form a compound of Formula (4): wherein OX represents a leaving group; and c) coupling the compound of Formula (4) to a compound of Formula (5): to form a compound of Formula (1). A stereoselective reduction of ketones to alcohols is also disclosed.
• Stereoselective Preparation of a Cyclopentane-Based NK1 Receptor Antagonist Bearing an Unsymmetrically Substituted Sec−Sec Ether
  作者：Jeffrey T. Kuethe、Jean-Francois Marcoux、Audrey Wong、Jimmy Wu、Michael C. Hillier、Peter G. Dormer、Ian W. Davies、David L. Hughes

  DOI：10.1021/jo061268x

  日期：2006.9.1

  A highly efficient synthesis of the potent and selective NK-1 receptor antagonist 1 is described. The key transformation involved the etherification reaction between cyclopentanol 12 and chiral imidate 30 which was catalyzed by HBF4 to initially give ether 14 as a 17:1 mixture of diastereomers and in 75% combined yield. The diastereoselectivity was upgraded to 109:1 by crystallization of the triethylamine solvate 44 which was isolated in 54% yield from 12. Mechanistic studies confirmed that the etherification reaction proceeds through an unprecedented S(N)2 reaction pathway under typical S(N)1 reaction conditions.
• WO2006/67395
  申请人：——

  公开号：——

  公开（公告）日：——