(+/-)-trans-3-oxo-2-(4-fluorophenyl)cyclopentane carboxylic acid methyl ester

• 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: (+/-)-trans-3-oxo-2-(4-fluorophenyl)cyclopentane carboxylic acid methyl ester
• 英文别名: methyl 3-keto-2-(4-fluorophenyl)cyclopentanecarboxylate；methyl (1S,2S)-2-(4-fluorophenyl)-3-oxocyclopentane-1-carboxylate
• 化学式: C₁₃H₁₃FO₃
• 分子量: 236.243
• InChiKey: PRCNOVNDQLDNEZ-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-3-oxo-2-(4-fluorophenyl)cyclopentane carboxylic acid methyl ester 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate
  参考文献：
  名称：

  Cyclopentane-based human NK1 antagonists. Part 2: Development of potent, orally active, water-soluble derivatives

  摘要：

  The synthesis and optimization of a cyclopentane-based hNK1 antagonist scaffold 3, having four chiral centers, will be discussed in the context of its enhanced water-solubility properties relative to the marketed anti-emetic hNK1 antagonist EMEND (R) (Aprepitant). Sub-nanomolar hNK1 binding was achieved and oral activity comparable to Aprepitant in two in vivo models will be described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.044
• 作为产物：
  描述：

  methyl 2-(4-fluorophenyl)-3-oxo-1-cyclopent-1-enecarboxylate 在 1,4-dihydronicotinamide adenine dinucleotide 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (+/-)-trans-3-oxo-2-(4-fluorophenyl)cyclopentane carboxylic acid methyl ester 、 methyl (1R,2R)-2-(4-fluorophenyl)-3-oxocyclopentane-1-carboxylate 、 Methyl trans-(+/-)-2-(4-fluorophenyl)cyclopentan-3-one-1-carboxylate
  参考文献：
  名称：

  Asymmetric bioreduction of α,β-unsaturated nitriles and ketones

  摘要：

  Two applications for the asymmetric reduction of activated alkenes employing isolated enoate reductases are reported. A series of alpha,beta-unsturated nitriles were shown to be converted to the optically active nitrile products in high yields and excellent enantioselectivities (up to 99% ee). In addition, the reduction of 2,3-disubstituted cyclopenteriones was shown to provide almost exclusively trans-2,3-disubstituted cyclopentanones in high yield and enantiopurity (94% ee). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.023

文献信息

• Expeditious synthesis of tri-substituted cyclopentane derivatives
  作者：Ranjit C Desai、Peter Cicala、Laura C Meurer、Paul E Finke

  DOI：10.1016/s0040-4039(02)00901-2

  日期：2002.5

  An efficient preparation of the cyclopentane scaffold 2, a key precursor to the potent human NK1 antagonist 1 having three contiguous chiral centers is described.

  描述了有效制备环戊烷支架2的方法，环戊烷支架2是具有三个连续手性中心的有效人NK1拮抗剂1的关键前体。
• QUINOLINE AND NAPHTHYRIDINE CARBOXYLIC ACID ANTIBACTERIALS
  申请人：ABBOTT LABORATORIES

  公开号：EP1226146A2

  公开（公告）日：2002-07-31
• ZWITTERIONIC TACHYKININ RECEPTOR ANTAGONISTS
  申请人：Merck & Co., Inc.

  公开号：EP1322596B1

  公开（公告）日：2007-08-15
• US5750549A
  申请人：——

  公开号：US5750549A

  公开（公告）日：1998-05-12
• US5877191A
  申请人：——

  公开号：US5877191A

  公开（公告）日：1999-03-02