2-[(1R)-1-(3-fluorophenyl)prop-2-enyl]propanedioic acid | 1026720-66-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-[(1R)-1-(3-fluorophenyl)prop-2-enyl]propanedioic acid
• CAS: 1026720-66-0
• 化学式: C₁₂H₁₁FO₄
• 分子量: 238.215
• InChiKey: MMHVCSAQDZPCBT-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(1R)-1-(3-fluorophenyl)prop-2-enyl]propanedioic acid 在 盐酸 、 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 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 45.0h， 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：

  3-氟苯甲醛 在 hexacarbonyl molybdenum 、 (1S,2S)-1,2-二(2-吡啶碳酰胺)环己烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 2-[(1R)-1-(3-fluorophenyl)prop-2-enyl]propanedioic 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

• 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.