(3aS,4S,5S,7aR)-4-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carbaldehyde

• 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: (3aS,4S,5S,7aR)-4-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carbaldehyde
• 英文别名: (3aS,4S,5S,7aR)-2,2-dimethyl-4-[(2E)-6-methylhepta-2,5-dien-2-yl]-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5-carbaldehyde
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: AXIDONCRBNEJBQ-YKGQPRCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5S,7aR)-4-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carbaldehyde 在 碳酸氢钠 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 1.5h， 生成 Acetic acid (3aR,4R,5S,7aS)-5-[(E)-cyclohexyliminomethyl]-4-((E)-1,5-dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester
  参考文献：
  名称：

  A Concise Synthesis of Fumagillol

  摘要：

  A 13-step synthesis of (±)-fumagillol (1), the direct precursor of the potent angiogenesis inhibitors TNP-470 and fumagillin, from crotonaldehyde, diethylamine, and acrolein (see the scheme) has been achieved. The synthesis features a remarkable hetero-Claisen rearrangement. Small-molecule inhibitors of angiogenesis are promising chemotherapeutic agents for the treatment of cancer and inflammatory diseases.

  DOI：

  10.1002/(sici)1521-3773(19990401)38:7<971::aid-anie971>3.0.co;2-w
• 作为产物：
  描述：

  1,3-环己二烯-1-甲醛 在 四氧化锇 、 potassium tert-butylate 、 叔丁基锂 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 异丙醇 、 叔丁醇 为溶剂， 反应 4.08h， 生成 (3aS,4S,5S,7aR)-4-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  A Concise Synthesis of Fumagillol

  摘要：

  A 13-step synthesis of (±)-fumagillol (1), the direct precursor of the potent angiogenesis inhibitors TNP-470 and fumagillin, from crotonaldehyde, diethylamine, and acrolein (see the scheme) has been achieved. The synthesis features a remarkable hetero-Claisen rearrangement. Small-molecule inhibitors of angiogenesis are promising chemotherapeutic agents for the treatment of cancer and inflammatory diseases.

  DOI：

  10.1002/(sici)1521-3773(19990401)38:7<971::aid-anie971>3.0.co;2-w

文献信息

• A Concise Synthesis of Fumagillol
  作者：David A. Vosburg、Sven Weiler、Erik J. Sorensen

  DOI：10.1002/(sici)1521-3773(19990401)38:7<971::aid-anie971>3.0.co;2-w

  日期：1999.4.1

  A 13-step synthesis of (±)-fumagillol (1), the direct precursor of the potent angiogenesis inhibitors TNP-470 and fumagillin, from crotonaldehyde, diethylamine, and acrolein (see the scheme) has been achieved. The synthesis features a remarkable hetero-Claisen rearrangement. Small-molecule inhibitors of angiogenesis are promising chemotherapeutic agents for the treatment of cancer and inflammatory diseases.