(1S,3S,5R)-3-(carbomethoxy)-4,4,5-trimethylcyclopentanecarboxylic acid | 307306-66-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3S,5R)-3-(carbomethoxy)-4,4,5-trimethylcyclopentanecarboxylic acid
• 英文别名: (1S,3S,5R)-3-Carboxymethyl-4,4,5-trimethylcyclopentanecarboxylic acid；(1S,2R,4S)-4-methoxycarbonyl-2,3,3-trimethylcyclopentane-1-carboxylic acid
• CAS: 307306-66-7
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: CYOZPPMSSSDWBU-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3S,5R)-3-(carbomethoxy)-4,4,5-trimethylcyclopentanecarboxylic acid 在 硼烷 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 57.0h， 生成 (1S,3S,4R)-methyl 3-(hydroxymethyl)-4,5,5-trimethylcyclopentanecarboxylate xanthate
  参考文献：
  名称：

  Defense mechanisms of arthropods. 84. Synthesis of (-)-.alpha.-necrodol and (-)-.beta.-necrodol: novel cyclopentanoid terpenes from a carrion beetle

  摘要：

  DOI：

  10.1021/jo00300a021
• 作为产物：
  描述：

  methyl phenylcamphorate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 96.0h， 以75%的产率得到(1S,3S,5R)-3-(carbomethoxy)-4,4,5-trimethylcyclopentanecarboxylic acid
  参考文献：
  名称：

  Synthesis of (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene — a trifluoromethyl analogue of necrodols

  摘要：

  New trifluoromethyl group containing enantiomerically pure monoterpene derivatives, methyl (1S,3R,4S)-(+)-3-(trifluoromethyl)-2,2,3-trimethylcyclopentanecarboxylate (6); methyl (3S,4R)-(+)-3-(trifluoromethyl)-4,5,5-trimethylcyclopentenecarboxylate (10) and (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene (1), were prepared using camphoric anhydride as the starting material and sulphur tetrafluoride as the fluorinating agent. Compound 1 is a trifluoromethyl analogue of an unknown isomer of necrodols. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(00)00283-9

文献信息

• Defense mechanisms of arthropods. 84. Synthesis of (-)-.alpha.-necrodol and (-)-.beta.-necrodol: novel cyclopentanoid terpenes from a carrion beetle
  作者：Robert T. Jacobs、Geoffrey I. Feutrill、Jerrold Meinwald

  DOI：10.1021/jo00300a021

  日期：1990.6
• Synthesis of (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene — a trifluoromethyl analogue of necrodols
  作者：Wojciech Dmowski、Krystyna Piasecka-Maciejewska

  DOI：10.1016/s0022-1139(00)00283-9

  日期：2000.7

  New trifluoromethyl group containing enantiomerically pure monoterpene derivatives, methyl (1S,3R,4S)-(+)-3-(trifluoromethyl)-2,2,3-trimethylcyclopentanecarboxylate (6); methyl (3S,4R)-(+)-3-(trifluoromethyl)-4,5,5-trimethylcyclopentenecarboxylate (10) and (3S,4R)-(+)-hydroxymethyl-3-(trifluoromethyl)-4,5,5-trimethylcyclopentene (1), were prepared using camphoric anhydride as the starting material and sulphur tetrafluoride as the fluorinating agent. Compound 1 is a trifluoromethyl analogue of an unknown isomer of necrodols. (C) 2000 Elsevier Science S.A. All rights reserved.