1-tert-Butyl-benzocyclobuten | 25402-81-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-tert-Butyl-benzocyclobuten
• 英文别名: 7-tert-Butylbicyclo[4.2.0]octa-1,3,5-triene
• CAS: 25402-81-7
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: PCNJMWIUWZWHDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-tert-Butyl-benzocyclobuten 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 生成 1-Brom-1-tert.-butyl-benzocyclobuten
  参考文献：
  名称：

  Mueller,E. et al., Synthesis, 1970, p. 82 - 83

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2,2-Dimethylpropyl)benzoic acid 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 chromium trioxide-pyridine complex 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 溶剂黄146 、 苯 为溶剂， 反应 19.75h， 生成 1-tert-Butyl-benzocyclobuten
  参考文献：
  名称：

  Intramolecular Reactivity of Arylcarbenes: Derivatives of o-Tolylcarbene

  摘要：

  Various CH(2)X groups have been attached to the ortho position of phenylcarbene. If 2'- or 3'-C-H bonds are present, as in 23 (X = Me), 71 (X = CMe(3)), and 58 (X = SiMe(3)), C-H insertion leading to five- or six-membered rings predominates in the gas phase and competes with intermolecular reactions in solution. The formation of benzocyclobutenes via insertion into 1'-C-H bonds is a very minor reaction path of 23 and 71. In contrast, 58 produces substantial amounts of the benzocyclobutene 59 by way of C-Si insertion, particularly in the gas phase. Insertion into the Si-Me bonds of 58 also occurs while the C-F bonds of 37 (X = CF3) and 50 (X = Fl are inert. In the gas phase, 37 and 50 give mainly benzocyclobutenes whereas intermolecular reactions prevail in solution. The effects of sensitization and of solvent polarity suggest that benzocyclobutenes arise from singlet arylcarbenes. The amount of carbene-carbene rearrangement decreases in the order 7 (X = H) > 37 (X = CF3) > 23 (X = Me); no rearrangement was observed with 50 (X = Fl, 58 (X = SiMe(3)), and 71 (X = CMe(3)).

  DOI：

  10.1021/jo00093a014

文献信息

• Bubb,W.A.; Sternhell,S., Australian Journal of Chemistry, 1976, vol. 29, p. 1685 - 1697
  作者：Bubb,W.A.、Sternhell,S.

  DOI：——

  日期：——
• Intramolecular Reactivity of Arylcarbenes: Derivatives of o-Tolylcarbene
  作者：Wolfgang Kirmse、Wolfgang Konrad、Dirk Schnitzler

  DOI：10.1021/jo00093a014

  日期：1994.7

  Various CH(2)X groups have been attached to the ortho position of phenylcarbene. If 2'- or 3'-C-H bonds are present, as in 23 (X = Me), 71 (X = CMe(3)), and 58 (X = SiMe(3)), C-H insertion leading to five- or six-membered rings predominates in the gas phase and competes with intermolecular reactions in solution. The formation of benzocyclobutenes via insertion into 1'-C-H bonds is a very minor reaction path of 23 and 71. In contrast, 58 produces substantial amounts of the benzocyclobutene 59 by way of C-Si insertion, particularly in the gas phase. Insertion into the Si-Me bonds of 58 also occurs while the C-F bonds of 37 (X = CF3) and 50 (X = Fl are inert. In the gas phase, 37 and 50 give mainly benzocyclobutenes whereas intermolecular reactions prevail in solution. The effects of sensitization and of solvent polarity suggest that benzocyclobutenes arise from singlet arylcarbenes. The amount of carbene-carbene rearrangement decreases in the order 7 (X = H) > 37 (X = CF3) > 23 (X = Me); no rearrangement was observed with 50 (X = Fl, 58 (X = SiMe(3)), and 71 (X = CMe(3)).
• Mueller,E. et al., Synthesis, 1970, p. 82 - 83
  作者：Mueller,E. et al.

  DOI：——

  日期：——