1,6-divinylbicyclo<4.4.0>decane | 103478-38-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1,6-divinylbicyclo<4.4.0>decane
• CAS: 103478-38-2
• 化学式: C₁₄H₂₂
• 分子量: 190.329
• InChiKey: MVVYQKWKAUOUOZ-OKILXGFUSA-N

物化性质

• 沸点：
  239.4±10.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  6-<(tert-butyldimethylsilyl)oxy>cyclodecan-1-one 在 草酰氯 、 TiCl₃-1,2-dimethoxyethane 、 铜 、 magnesium 、 二甲基亚砜 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 13.0h， 生成 1,6-divinylbicyclo<4.4.0>decane
  参考文献：
  名称：

  Concerning attempts to synthesize out-bicyclo[4.4.4]tetradec-1-ene derivatives

  摘要：

  The keto aldehydes 4-[6-oxo-1-(tetrahydropyranyloxy)cyclodecyl]butanal (17), (E)-4-(6-oxocyclodec-1-enyl)butanal (24), and 4-(6-oxocyclodecylidene)butanal (7) have been synthesized. No bicyclo[4.4.4]tetradecadienes were found in the products from the zero-valent titanium reductive cyclization of compound 24. Instead, products arising from transannular reactions of the cyclodecyl ring system were isolated. 1,6-Divinylbicyclo[4.4.0]decane (32) was obtained from the reductive cyclization of keto enal 7. The most plausible route for its formation is through a Cope rearrangement of a bicyclo[4.4.4]tetradecene derivative, suggesting that an out-bicyclo[4.4.4]tetradecenylbistitanium pinacolate 8 intervened.

  DOI：

  10.1021/jo00052a024

文献信息

• Synthesis, bromination, and photoelectron spectra of meso-bridgehead dienes
  作者：K. J. Shea、A. C. Greeley、S. Nguyen、P. D. Beauchamp、D. H. Aue、J. S. Witzeman

  DOI：10.1021/ja00279a040

  日期：1986.9

  The Cope rearrangement of l,n-divinylbicycloalkanes has been employed for the synthesis of a series of meso-bridgehead dienes, molecules that contain two torsionally distorted carbon-carbon double bonds held in proximate relationship. The rate of Cope rearrangement does not correlate with reaction exothermicity or release of strain energy. A frontier molecular orbital explanation is one of several

  L,n-二乙烯基双环烷烃的 Cope 重排已被用于合成一系列中间桥头二烯，这些分子包含两个以近似关系保持的扭转扭曲的碳-碳双键。Cope 重排的速率与反应放热或应变能的释放无关。前沿分子轨道解释是解释这些观察结果的几个考虑因素之一。光谱（紫外和光电子光谱）和化学研究已经允许记录两个桥头双键的渐进跨环相互作用。