3-[4-[(4-chlorophenyl)sulfanyl]-4-(2,5-difluorophenyl)cyclohexyl]propanoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-[4-[(4-chlorophenyl)sulfanyl]-4-(2,5-difluorophenyl)cyclohexyl]propanoic acid
• 英文别名: 3-[4-(4-chlorophenyl)sulfanyl-4-(2,5-difluorophenyl)cyclohexyl]propanoic acid
• 化学式: C₂₁H₂₁ClF₂O₂S
• 分子量: 410.912
• InChiKey: TVMRSFUCFAMWON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[4-[(4-chlorophenyl)sulfanyl]-4-(2,5-difluorophenyl)cyclohexyl]propanoic acid 在 三氟甲磺酸 、 双氧水 、 溶剂黄146 、 4-氯苯硫酚 作用下， 以 正庚烷 、 甲苯 为溶剂， 生成 cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanepropanoic acid
  参考文献：
  名称：

  A Novel Crystallization-Induced Diastereomeric Transformation Based on a Reversible Carbon−Sulfur Bond Formation. Application to the Synthesis of a γ-Secretase Inhibitor

  摘要：

  This paper describes a remarkably efficient process for the preparation of gamma-secretase inhibitor 1. The target is synthesized in only five steps with an overall yield of 58%. The key operation is a highly selective and practical, crystallization-driven transformation for the conversion of a mixture of tertiary benzylic alcohols into the desired sulfide diastereomer with 94:6 dr. This unprecedented process is based upon a reversible carbon-sulfur bond formation under acidic conditions.

  DOI：

  10.1021/jo0705925
• 作为产物：
  描述：

  3-[4-(2,5-difluorophenyl)-4-hydroxycyclohexyl]propanoic acid 、 4-氯苯硫酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到3-[4-[(4-chlorophenyl)sulfanyl]-4-(2,5-difluorophenyl)cyclohexyl]propanoic acid
  参考文献：
  名称：

  A Novel Crystallization-Induced Diastereomeric Transformation Based on a Reversible Carbon−Sulfur Bond Formation. Application to the Synthesis of a γ-Secretase Inhibitor

  摘要：

  This paper describes a remarkably efficient process for the preparation of gamma-secretase inhibitor 1. The target is synthesized in only five steps with an overall yield of 58%. The key operation is a highly selective and practical, crystallization-driven transformation for the conversion of a mixture of tertiary benzylic alcohols into the desired sulfide diastereomer with 94:6 dr. This unprecedented process is based upon a reversible carbon-sulfur bond formation under acidic conditions.

  DOI：

  10.1021/jo0705925

文献信息

• [EN] STEREOSELECTIVE SYNTHESIS OF A 4,4-DISUBSTITUTED CYCLOHEXANEPROPANOIC ACID<br/>[FR] SYNTHESE STEREOSELECTIVE D'UN ACIDE CYCLOHEXANEPROPANOIQUE 4,4-DISUBSTITUE
  申请人：MERCK SHARP & DOHME

  公开号：WO2005080309A1

  公开（公告）日：2005-09-01

  There is provided a stereoselective route to a compound of formula (1): wherein R represents H or an alkali metal, Ar1 represents 4-chlorophenyl and Ar2 represents 2,5-difluorophenyl.

  提供了一种立体选择性路线到一个化合物的结构式（1）：其中R代表H或碱金属，Ar1代表4-氯苯基，Ar2代表2,5-二氟苯基。
• Stereoselective Synthesis of a 4,4-Disubstituted Cyclohexanepropanoic Acid
  申请人：Brands Marie Joseph Karel

  公开号：US20070225520A1

  公开（公告）日：2007-09-27

  There is provided stereoselective route to a compound of formula I: wherein R represents H or an alkali metal, Ar 1 represents 4-chlorophenyl and Ar 2 represents 2,5-difluorophenyl.

  提供了一种立体选择性的合成路线，用于合成化合物I的式子：其中R代表氢或碱金属，Ar1代表4-氯苯基，Ar2代表2,5-二氟苯基。
• STEREOSELECTIVE SYNTHESIS OF A 4,4-DISUBSTITUTED CYCLOHEXANEPROPANOIC ACID
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP1718593B1

  公开（公告）日：2007-07-25
• US7411088B2
  申请人：——

  公开号：US7411088B2

  公开（公告）日：2008-08-12
• A Novel Crystallization-Induced Diastereomeric Transformation Based on a Reversible Carbon−Sulfur Bond Formation. Application to the Synthesis of a γ-Secretase Inhibitor
  作者：Antony J. Davies、Jeremy P. Scott、Brian C. Bishop、Karel M. J. Brands、Sarah E. Brewer、Jimmy O. DaSilva、Peter G. Dormer、Ulf-H. Dolling、Andrew D. Gibb、Deborah C. Hammond、David R. Lieberman、Michael Palucki、Joseph F. Payack

  DOI：10.1021/jo0705925

  日期：2007.6.1

  This paper describes a remarkably efficient process for the preparation of gamma-secretase inhibitor 1. The target is synthesized in only five steps with an overall yield of 58%. The key operation is a highly selective and practical, crystallization-driven transformation for the conversion of a mixture of tertiary benzylic alcohols into the desired sulfide diastereomer with 94:6 dr. This unprecedented process is based upon a reversible carbon-sulfur bond formation under acidic conditions.