(1aS,8bR)-1,1-Dimethyl-1a,2,3,8b-tetrahydro-1H-benzo[a]cyclopropa[c]cyclohepten-4-one | 120710-31-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (1aS,8bR)-1,1-Dimethyl-1a,2,3,8b-tetrahydro-1H-benzo[a]cyclopropa[c]cyclohepten-4-one
• 英文别名: (2R,4S)-3,3-dimethyltricyclo[6.4.0.02,4]dodeca-1(12),8,10-trien-7-one
• CAS: 120710-31-8
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: AJIVGNBDHBPGGU-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1aS,8bR)-1,1-Dimethyl-1a,2,3,8b-tetrahydro-1H-benzo[a]cyclopropa[c]cyclohepten-4-one 在 二异丁基氢化铝 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 0.08h， 以88%的产率得到
  参考文献：
  名称：

  General Photoisomerization Approach to trans-Benzobicyclo[5.1.0]octenes: Synthetic and Mechanistic Studies

  摘要：

  The preparation and photoisomerization of cis-bicyclo[5.1.0]octenes (+)-3, 16, and 21-23 are described. For the benzannulated substrates, the primary photochemical events established photostationary states between the cis isomers and the trans-fused cyclopropanes (+)-9, 32, 37, and 44. Studies employing enantioenriched 21, 32, and 44 demonstrated that the reactions occurred primarily but not exclusively via cleavage of the peripheral benzylic cyclopropane bonds. Utilization of the triplet quencher piperylene revealed a predominance of triplet diradical intermediates in the trans-to-cis conversions and afforded an improved protocol for preparative isomerizations.

  DOI：

  10.1021/jo00101a025
• 作为产物：
  描述：

  (2'R,4'S)-3',3'-dimethylspiro[1,3-dioxolane-2,7'-tricyclo[6.4.0.02,4]dodeca-1(12),8,10-triene] 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (1aS,8bR)-1,1-Dimethyl-1a,2,3,8b-tetrahydro-1H-benzo[a]cyclopropa[c]cyclohepten-4-one
  参考文献：
  名称：

  General Photoisomerization Approach to trans-Benzobicyclo[5.1.0]octenes: Synthetic and Mechanistic Studies

  摘要：

  The preparation and photoisomerization of cis-bicyclo[5.1.0]octenes (+)-3, 16, and 21-23 are described. For the benzannulated substrates, the primary photochemical events established photostationary states between the cis isomers and the trans-fused cyclopropanes (+)-9, 32, 37, and 44. Studies employing enantioenriched 21, 32, and 44 demonstrated that the reactions occurred primarily but not exclusively via cleavage of the peripheral benzylic cyclopropane bonds. Utilization of the triplet quencher piperylene revealed a predominance of triplet diradical intermediates in the trans-to-cis conversions and afforded an improved protocol for preparative isomerizations.

  DOI：

  10.1021/jo00101a025

文献信息

• An efficient photochemical approach to the trans-bicyclo[5.1.0]octene ring system
  作者：John L. Wood、Nigel J. Liverton、Melean Visnick、Amos B. Smith

  DOI：10.1021/ja00194a076

  日期：1989.6