(1RS,2SR)-2-(1-methylene-2-propenyl)cyclopentanecarboxaldehyde

• 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: (1RS,2SR)-2-(1-methylene-2-propenyl)cyclopentanecarboxaldehyde
• 英文别名: (1R,2S)-2-buta-1,3-dien-2-ylcyclopentane-1-carbaldehyde
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: ATBFMAVAJGWKAA-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-环戊烯甲醛 、 N'-but-3-en-2-ylidenehydrazono-2,4,6-tri-isopropylphenylbenzenesulphonohydrazide 生成 (1RS,2SR)-2-(1-methylene-2-propenyl)cyclopentanecarboxaldehyde 、 (1RS,2RS)-2-(1-methylene-2-propenyl)cyclopentanecarboxaldehyde
  参考文献：
  名称：

  Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms

  摘要：

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.

  DOI：

  10.1021/jo702635t

文献信息

• Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms
  作者：Derrick L. J. Clive、Dazhan Liu

  DOI：10.1021/jo702635t

  日期：2008.4.1

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.