1,4-dicyclopent-1-enylbutane | 52403-94-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,4-dicyclopent-1-enylbutane
• 英文别名: Bis-(2-(1'-cyclopentenyl)-ethyl)；Bis-[2-(1'-cyclopentenyl)-ethyl]；1-[4-(Cyclopenten-1-yl)butyl]cyclopentene
• CAS: 52403-94-8
• 化学式: C₁₄H₂₂
• 分子量: 190.329
• InChiKey: HZYZRBIIRMCQPE-UHFFFAOYSA-N

物化性质

• 沸点：
  277.7±10.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-dicyclopent-1-enylbutane 在 Pt-oxide 氢气 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以94%的产率得到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-羟基环癸烷-1-酮 在 4-二甲氨基吡啶 、 TiCl₃-1,2-dimethoxyethane 、 4 A molecular sieve 、 sodium acetate 、 铜 、 magnesium 、 三乙胺 、 pyridinium chlorochromate 、 锌 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 60.17h， 生成 1,4-dicyclopent-1-enylbutane
  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

• HOMOALLYLIC REARRANGEMENTS OF 4-SPIRO[2.4]HEPTYL RADICAL AND 4-SPIRO[2.5]OCTYL RADICAL
  作者：Mikio Suzuki、Shun-Ichi Murahashi、Akio Sonoda、Ichiro Moritani

  DOI：10.1246/cl.1974.267

  日期：1974.3.5

  Irradiation of azobis(4-spiro[2.4]heptane) and azobis(4-spiro[2.5]octane) afforded homoallylically rearranged products via the corresponding titled radicals, in which the rigid geometry locks the cyclopropylcarbinyl radical in the stable bisected conformation.

  偶氮二(4-螺[2.4]庚烷)和偶氮二(4-螺[2.5]辛烷)的辐照通过相应的标题基团提供同烯丙基重排产物，其中刚性几何结构将环丙基羰基基团锁定在稳定的二等分构象中。