(3aS,7aR)-2,2-Dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,7aR)-2,2-Dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carbaldehyde
• 英文别名: (3aS,7aR)-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carbaldehyde
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: YXFGHMPWCBMQLR-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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,7aR)-2,2-Dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carbaldehyde 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 水 、 叔丁基锂 、 sodium acetate 、 碳酸氢钠 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.28h， 生成 (3R,4S,5S,6R)-4-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-1-oxa-spiro[2.5]octane-5,6-diol
  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 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 (3aS,7aR)-2,2-Dimethyl-3a,6,7,7a-tetrahydro-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

• Simple and efficient synthesis of highly functionalized cyclohexanes; formal total synthesis of ovalicin and fumagillin
  作者：Shunya Takahashi、Yayoi Hongo、Yue Qi Ye、Hiroyuki Koshino

  DOI：10.1016/j.tetasy.2011.03.015

  日期：2011.3

  Two chiral cyclohexanes 4 and 6, which are key intermediates for the total synthesis of ovalicin 1 and fumagillin 2, respectively, were synthesized from (2R,3S) 1,2-epoxy-4-penten-3-ol. The key steps involve an efficient construction of divinylalcohol 7 using methallyl Grignard reagent 9c, and an intramolecular olefin metathesis of 7. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.