4-<6-<(tert-butyldimethylsilyl)oxy>-1-(tetrahydropyranyloxy)cyclodecyl>butan-1-ol | 144493-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-<6-<(tert-butyldimethylsilyl)oxy>-1-(tetrahydropyranyloxy)cyclodecyl>butan-1-ol
• 英文别名: 4-[6-[Tert-butyl(dimethyl)silyl]oxy-1-(oxan-2-yloxy)cyclodecyl]butan-1-ol
• CAS: 144493-57-2；144541-33-3
• 化学式: C₂₅H₅₀O₄Si
• 分子量: 442.755
• InChiKey: FPQZPTCZEMXMKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-<6-<(tert-butyldimethylsilyl)oxy>-1-(tetrahydropyranyloxy)cyclodecyl>butan-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以82%的产率得到4-<6-hydroxy-1-(tetrahydropyranyloxy)cyclodecyl>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
• 作为产物：
  描述：

  6-羟基环癸烷-1-酮 在 4-二甲氨基吡啶 、 双氧水 、 4-甲基苯磺酸吡啶 、 二(3-甲基丁烷-2-基)硼烷 、 magnesium 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 100.0h， 生成 4-<6-<(tert-butyldimethylsilyl)oxy>-1-(tetrahydropyranyloxy)cyclodecyl>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