1-Methyl-1-(2-methyl-1,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene | 134816-84-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-Methyl-1-(2-methyl-1,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene
• 英文别名: 1-Methyl-1-(2-methyl-1,3-diphenylcycloprop-2-en-1-yl)-3-phenylindene
• CAS: 134816-84-5；134816-85-6
• 化学式: C₃₂H₂₆
• 分子量: 410.558
• InChiKey: CBNVMLLWEYDZAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 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-Methyl-1-(2-methyl-1,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene 在 氘代吡啶 作用下， 以 四氯化碳 为溶剂， 反应 133.0h， 以95%的产率得到1-Methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene
  参考文献：
  名称：

  Studies dealing with cycloaddition and sigmatropic reactions of cyclopropenyl-substituted indenes

  摘要：

  The thermal and photochemical reactions of a number of substituted cyclopropenylindenes have been studied. The thermolysis of these systems resulted in a series of 3,3-sigmatropic rearrangements. The product distribution parallels the expected relative order of thermodynamic stabilities of the indenes. The major product obtained upon extended heating corresponds to the isomer in which the double bonds are in conjugation with the phenyl groups on both the indene and cyclopropene rings. Direct irradiation of 1-methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene afforded a mixture of unsymmetrical cyclopropenes together with a cyclopropa[cd]pentalene. The formation of the products can be rationalized in terms of two competing pathways. One path involves sigma-bond cleavage to produce a diradical pair which undergoes recombination to give the rearranged cyclopropene. The alternate pathway proceeds by ring opening of the singlet state of the cyclopropene to a vinylcarbene intermediate. Attack of the vinylcarbene carbon on the neighboring double bond produces the cyclopropa[cd]pentalene ring skeleton. The sensitized photolysis was found to give intramolecular [2 + 2]-cycloadducts. The observed regiospecificity of the reaction is understandable in terms of formation of the most stable diradical intermediate.

  DOI：

  10.1021/jo00015a033
• 作为产物：
  描述：

  1-(1-Methyl-2,3-diphenyl-2-cyclopropen-1-yl)-3-methyl-1-phenylindene 以 苯 为溶剂， 生成 1-Methyl-1-(2-methyl-1,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene
  参考文献：
  名称：

  Studies dealing with cycloaddition and sigmatropic reactions of cyclopropenyl-substituted indenes

  摘要：

  The thermal and photochemical reactions of a number of substituted cyclopropenylindenes have been studied. The thermolysis of these systems resulted in a series of 3,3-sigmatropic rearrangements. The product distribution parallels the expected relative order of thermodynamic stabilities of the indenes. The major product obtained upon extended heating corresponds to the isomer in which the double bonds are in conjugation with the phenyl groups on both the indene and cyclopropene rings. Direct irradiation of 1-methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-1-yl)-3-phenylindene afforded a mixture of unsymmetrical cyclopropenes together with a cyclopropa[cd]pentalene. The formation of the products can be rationalized in terms of two competing pathways. One path involves sigma-bond cleavage to produce a diradical pair which undergoes recombination to give the rearranged cyclopropene. The alternate pathway proceeds by ring opening of the singlet state of the cyclopropene to a vinylcarbene intermediate. Attack of the vinylcarbene carbon on the neighboring double bond produces the cyclopropa[cd]pentalene ring skeleton. The sensitized photolysis was found to give intramolecular [2 + 2]-cycloadducts. The observed regiospecificity of the reaction is understandable in terms of formation of the most stable diradical intermediate.

  DOI：

  10.1021/jo00015a033