cis-bicyclo<5.4.0>undecane | 1502-19-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: cis-bicyclo<5.4.0>undecane
• 英文别名: cis-Bicyclo<5.4.0>undecan；cis-Bicyclo[5.4.0]undecan；cis-Bicyclo[5.4.0]undecane；(4aS,9aR)-2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-benzo[7]annulene
• CAS: 1502-19-8
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: GBCQLGDTLMHVHU-PHIMTYICSA-N

物化性质

• 沸点：
  88.5-89 °C(Press: 11 Torr)
• 密度：
  0.9014 g/cm3
• 保留指数：
  1226

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (+/-)-2-oxo-cis-decahydro-1H-benzocycloheptene 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 生成 cis-bicyclo<5.4.0>undecane
  参考文献：
  名称：

  Transannular reactions of cycloalkenes, cycloalkadienes and cycloalkatrienes. 16. Photocyclization of cyclononene and cycloundecene

  摘要：

  Irradiation of cyclononene (7b) and cycloundecene (7d) in pentane afforded cis-bicyclo[4.3.0]nonane (10b) and cis-bicyclo[6.3.0]undecane (10d), respectively. Small amounts of the fragmentation products 1-undecene (14d) and 1-undecyne (15d) were also obtained from cycloundecene (7d). The photobehavior of the series of medium- and large-ring alkenes 7a-e is compared. Aside from E reversible Z isomerization, the principal pathway in each case involves rearrangement of the pi,R(3s) excited state to the cycloalkylidene intermediate 8, which undergoes predominant, if not exclusive, 1,5-transannular insertion to afford the corresponding cis-bicyclo[n.3.0]alkane (10). The cycloalkylidenes 8 formed in this way exhibit behavior somewhat different from those generated by other methods. The possible contributory role of carbene intermediates derived from pi,R(3s) excited states in E revesible Z photoisomerization of acyclic alkenes is also discussed.

  DOI：

  10.1021/jo00013a041

文献信息

• Granger,R. et al., Bulletin de la Societe Chimique de France, 1967, p. 1951 - 1956
  作者：Granger,R. et al.

  DOI：——

  日期：——
• Photochemistry of trans-fused bicyclo[4.n.0] 2,4-dienes. Ground-state conformational control in rigid systems
  作者：William G. Dauben、Eric G. Olsen

  DOI：10.1021/jo01305a001

  日期：1980.8