1-cyano-2,3-benzobicyclo<4.2.0>octa-2,4,7-triene | 133157-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1-cyano-2,3-benzobicyclo<4.2.0>octa-2,4,7-triene
• 英文别名: 2aH-cyclobuta[a]naphthalene-8b-carbonitrile
• CAS: 133157-21-8
• 化学式: C₁₃H₉N
• 分子量: 179.221
• InChiKey: VWCHQQYCJOVJQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-cyano-2,3-benzobicyclo<4.2.0>octa-2,4,7-triene 以2%的产率得到
  参考文献：
  名称：

  BENDER, CHRISTOPHER OWEN;CLYNE, DEAN SUTHERLAND;DOLMAN, DOUGLAS, CAN. J. CHEM., 69,(1991) N, C. 70-76

  摘要：

  DOI：
• 作为产物：
  描述：

  5-cyanobenzocyclooctatetraene 以42%的产率得到
  参考文献：
  名称：

  BENDER, CHRISTOPHER OWEN;CLYNE, DEAN SUTHERLAND;DOLMAN, DOUGLAS, CAN. J. CHEM., 69,(1991) N, C. 70-76

  摘要：

  DOI：

文献信息

• Photochemistry of 4-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene
  作者：Christopher Owen Bender、Douglas Dolman、Noah Tu

  DOI：10.1021/jo00017a007

  日期：1991.8

  4-Cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (11) was found to be thermally and photochemically reactive. Heating solutions of 11 at 150-degrees-C for 2 h gave 5-cyanobenzocyclooctatetraene (10) quantitatively. The direct irradiation of triene 11 gave 2-cyanobenzosemibullvalene (i.e., SB 12, 63%, PHI = 0.067), COT 10 (28%, PHI = 0.031), and 1-cyanonaphthalene (ca. 0.5%, PHI = 0.0005). Upon sensitization with p-(dimethylamino)benzophenone, 11 gave 12 (30%, PHI = 0.028), COT 10 (9%, PHI = 0.0093), and 1-cyanonaphthalene (2%, PHI = 0.0018). Studies with deuterium-labeled triene (11a) revealed that the semibullavene produced from direct irradiation possessed a different label distribution to that obtained from sensitized irradiation, and hence state-dependent pathways operate in the SB formation. The mechanism proposed for the SB formation from S1 of 11 involves a 1,2-shift with cleavage of the cyclobutene C1-C6 bond of the triene, while SB formation from T1 results from a Zimmerman di-pi-methane rearrangement.
• Bender, Christopher Owen; Clyne, Dean Sutherland; Dolman, Douglas, Canadian Journal of Chemistry, 1991, vol. 69, # 1, p. 70 - 76
  作者：Bender, Christopher Owen、Clyne, Dean Sutherland、Dolman, Douglas

  DOI：——

  日期：——