(3S)-3-(3-fluorophenyl)-4-pentenoic acid | 395065-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (3S)-3-(3-fluorophenyl)-4-pentenoic acid
• 英文别名: (3S)-3-(3-fluorophenyl)pent-4-enoic acid
• CAS: 395065-66-4
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: QLQKULXZTGONJM-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-(3-fluorophenyl)-4-pentenoic acid 在 sodium hydroxide 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 N,N'-羰基二咪唑 、 magnesium chloride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one
  参考文献：
  名称：

  Development of a New and Practical Route to Chiral 3,4-Disubstituted Cyclopentanones:  Asymmetric Alkylation and Intramolecular Cyclopropanation as Key C−C Bond-Forming Steps

  摘要：

  An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.

  DOI：

  10.1021/jo025890a
• 作为产物：
  描述：

  1-(3-氟苯基)丙-2-烯基甲基碳酸酯 在 盐酸 、 hexacarbonyl molybdenum 、 (1S,2S)-1,2-二(2-吡啶碳酰胺)环己烷 作用下， 以 水 、 甲苯 为溶剂， 反应 30.0h， 生成 (3S)-3-(3-fluorophenyl)-4-pentenoic acid
  参考文献：
  名称：

  Development of a New and Practical Route to Chiral 3,4-Disubstituted Cyclopentanones:  Asymmetric Alkylation and Intramolecular Cyclopropanation as Key C−C Bond-Forming Steps

  摘要：

  An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.

  DOI：

  10.1021/jo025890a

文献信息

• N-cyclopentyl modulators of chemokine receptor activity
  申请人：——

  公开号：US20020120146A1

  公开（公告）日：2002-08-29

  The present invention is directed to compounds of the formula I: 1 (wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X, n, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CC R-3.

  本发明涉及式I的化合物：1（其中R1，R3，R4，R5，R6，R7，R8，X，n，x和y在此定义），这些化合物可用作趋化因子受体活性的调节剂。特别地，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。
• US6358979B1
  申请人：——

  公开号：US6358979B1

  公开（公告）日：2002-03-19
• US6593346B2
  申请人：——

  公开号：US6593346B2

  公开（公告）日：2003-07-15
• Development of a New and Practical Route to Chiral 3,4-Disubstituted Cyclopentanones:  Asymmetric Alkylation and Intramolecular Cyclopropanation as Key C−C Bond-Forming Steps
  作者：Michael Palucki、Joann M. Um、Nobuyoshi Yasuda、David A. Conlon、Fuh-Rong Tsay、Frederick W. Hartner、Yi Hsiao、Benjamin Marcune、Sandor Karady、David L. Hughes、Peter G. Dormer、Paul J. Reider

  DOI：10.1021/jo025890a

  日期：2002.8.1

  An efficient and practical asymmetric synthesis of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentanone (1) is described. An asymmetric Mo-catalyzed alkylation reaction was used to establish the first stereocenter and a Cu-catalyzed intramolecular diastereoselective cyclopropanation reaction was used to set the second stereocenter. The last step involved a one-pot ring-opening/deprotection/hydrolysis/decarboxylation sequence that furnished the desired product in good yield.