1-Ethyl-3-methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-3-yl)indene | 134816-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Ethyl-3-methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-3-yl)indene
• 英文别名: 1-Ethyl-3-methyl-1-(1-methyl-2,3-diphenylcycloprop-2-en-1-yl)indene
• CAS: 134816-86-7
• 化学式: C₂₈H₂₆
• 分子量: 362.514
• InChiKey: QSNSOCAPPOBIQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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-Ethyl-3-methyl-1-(1-methyl-2,3-diphenyl-2-cyclopropen-3-yl)indene 以50%的产率得到
  参考文献：
  名称：

  PADWA, ALBERT;CORDOVA, DIANA M.;PULWER, MITCHELL J., J. ORG. CHEM., 56,(1991) N5, C. 4747-4753

  摘要：

  DOI：
• 作为产物：
  描述：

  3-ethyl-1-methyl-1H-indene 、 (1-methyl-2,3-diphenylcycloprop-2-en-1-yl) perchlorate 以8%的产率得到
  参考文献：
  名称：

  PADWA, ALBERT;CORDOVA, DIANA M.;PULWER, MITCHELL J., J. ORG. CHEM., 56,(1991) N5, C. 4747-4753

  摘要：

  DOI：

文献信息

• Studies dealing with cycloaddition and sigmatropic reactions of cyclopropenyl-substituted indenes
  作者：Albert Padwa、Diana M. Cordova、Mitchell J. Pulwer

  DOI：10.1021/jo00015a033

  日期：1991.7

  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.