Crotocembraneic acid | 205577-55-5

• 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: Crotocembraneic acid
• 英文别名: (1Z,5E,9E,11E)-5,9-dimethyl-12-propan-2-ylcyclotetradeca-1,5,9,11-tetraene-1-carboxylic acid
• CAS: 205577-55-5
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: PJVZQWKLUCVIQA-RJVZQQKXSA-N

物化性质

• 熔点：
  109-111 °C
• 沸点：
  451.0±45.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Crotocembraneic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以92%的产率得到(1Z,5E,9E,11E)-12-Isopropyl-5,9-dimethylcyclotetradeca-1,5,9,11-tetraenylmethanol
  参考文献：
  名称：

  Enantioselective total synthesis of natural 11,12-epoxycembrene-C

  摘要：

  The first enantioselective total synthesis of (+)-11,12-epoxycembrene-C (1), a novel naturally occurring cembranoxide isolated from tropical marine soft coral, was achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from readily available starting materials. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00982-5
• 作为产物：
  描述：

  farnesyl acetate trisnoraldehyde 在 manganese(IV) oxide 、 hydroxide 、 lithium perchlorate 、 四氯化钛 、 potassium carbonate 、 锌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 6.0h， 生成 Crotocembraneic acid
  参考文献：
  名称：

  Enantioselective total synthesis of natural 11,12-epoxycembrene-C

  摘要：

  The first enantioselective total synthesis of (+)-11,12-epoxycembrene-C (1), a novel naturally occurring cembranoxide isolated from tropical marine soft coral, was achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from readily available starting materials. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00982-5

文献信息

• First enantioselective total synthesis of (natural) (+)-11,12-epoxy-11,12-dihydrocembrene-C and (−)-7,8-epoxy-7,8-dihydrocembrene-C
  作者：Zuosheng Liu、Weidong Z. Li、Lizeng Peng、Ying Li、Yulin Li

  DOI：10.1039/b007239g

  日期：——

  enantioselective total syntheses of (+)-11,12-epoxy-11,12-dihydrocembrene-C 1 and (−)-7,8-epoxy-7,8-dihydrocembrene-C 2, two naturally occurring cembranoxides isolated from tropical marine soft corals, are achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from readily available starting materials. The syntheses presented here

  11,12-环氧-11,12- dihydrocembrene-C -的第一对映选择性全合成（+）1和（ - ） - 7,8-环氧-7,8- dihydrocembrene-C 2中，两个天然存在的cembranoxides分离自热带海洋软珊瑚，被实现通过一般的方法通过采用分子内的McMurry偶联和尖锐的不对称环氧化作为易于获得的起始材料的关键步骤。这里提出的合成证明了Bowden等人的1（11 S，12 S）的绝对立体化学分配。两十年前，2的环氧构型相应地假设为（7 R，8 R）。
• Enantioselective total synthesis of natural 11,12-epoxycembrene-C
  作者：Yulin Li、Zuosheng Liu、Jiong Lan、Jing Li、Lizeng Peng、Weidong Z Li、Ying Li、Albert S.C Chan

  DOI：10.1016/s0040-4039(00)00982-5

  日期：2000.9

  The first enantioselective total synthesis of (+)-11,12-epoxycembrene-C (1), a novel naturally occurring cembranoxide isolated from tropical marine soft coral, was achieved via a general approach by employing an intramolecular McMurry coupling and Sharpless asymmetric epoxidation as key steps from readily available starting materials. (C) 2000 Elsevier Science Ltd. All rights reserved.