(E)-4-(6-hydroxycyclodec-1-enyl)butan-1-ol | 144493-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-(6-hydroxycyclodec-1-enyl)butan-1-ol
• 英文别名: (5E)-6-(4-hydroxybutyl)cyclodec-5-en-1-ol
• CAS: 144493-66-3
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: PTKKWACVYUDJFK-NTUHNPAUSA-N

物化性质

• 沸点：
  365.5±42.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(6-hydroxycyclodec-1-enyl)butan-1-ol 在 Pt-oxide TiCl₃-1,2-dimethoxyethane 、 4 A molecular sieve 、 氢气 、 sodium acetate 、 铜 、 pyridinium chlorochromate 、 锌 作用下， 以 乙二醇二甲醚 、 乙醚 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 1,1'-(1,4-丁烷二基)二环戊烷
  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
• 作为产物：
  描述：

  6-<(tert-butyldimethylsilyl)oxy>cyclodecan-1-one 在 magnesium 作用下， 生成 (E)-4-(6-hydroxycyclodec-1-enyl)butan-1-ol
  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