optically inactive 2ξ-hydroxy-(4arH.9acH)-decahydro-1H-benzocycloheptene | 13837-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: optically inactive 2ξ-hydroxy-(4arH.9acH)-decahydro-1H-benzocycloheptene
• 英文别名: Opt.-inakt. 2ξ-Hydroxy-(4arH.9acH)-decahydro-1H-benzocyclohepten；(4aR,9aS)-2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-benzo[7]annulen-3-ol
• CAS: 13837-43-9；13837-44-0；16613-64-2；33817-80-0；33817-82-2
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: DVAMMVKOCADBBG-MTULOOOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  optically inactive 2ξ-hydroxy-(4arH.9acH)-decahydro-1H-benzocycloheptene 在 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
• 作为产物：
  描述：

  6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol 在 溶剂黄146 、 铂 作用下， 生成 optically inactive 2ξ-hydroxy-(4arH.9acH)-decahydro-1H-benzocycloheptene
  参考文献：
  名称：

  Zur Kenntnis des Kohlenstoffringes。Über顺式3.4-聚亚甲基-环己酮

  摘要：

  DOI：

  10.1002/hlca.19470300663