cis-1,2-di(4-methylphenyl)cyclopropane | 51009-44-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-1,2-di(4-methylphenyl)cyclopropane
• 英文别名: cis-1,2-Di-p-tolylcyclopropan；1-methyl-4-[(1S,2R)-2-(4-methylphenyl)cyclopropyl]benzene
• CAS: 51009-44-0
• 化学式: C₁₇H₁₈
• 分子量: 222.33
• InChiKey: SYKRKRUCIDVFLS-CALCHBBNSA-N

物化性质

• 沸点：
  148-150 °C(Press: 5 Torr)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  cis-1,2-di(4-methylphenyl)cyclopropane 在 9,10-二氰基蒽 作用下， 以 乙腈 为溶剂， 生成 trans-di(4-methylphenyl)cyclopropane
  参考文献：
  名称：

  Photochemistry of 9,10-dicyanoanthracene-1,2-diarylcyclopropane systems. Photocycloaddition and photoisomerization

  摘要：

  The photochemical reactions of 9,10-dicyanoanthracene (DCA)-1,2-diarylcyclopropane (CP) systems have been investigated. In degassed acetonitrile solution, (4-pi + 2-sigma) photocycloaddition between DCA and CP occurred to give cis- and trans-2,4-diaryl-1,5-dicyano-6,7:8,9-dibenzobicyclo[3.2.2]nona-6,8-dienes in a 3:1 ratio in good chemical yields although the quantum yields were not high (PHI = 0.002-0.04). This photocycloaddition did not occur in benzene. The DCA-sensitized photoisomerization of trans- and cis-1,2-bis(4-methoxyphenyl)cyclopropanes (1a and 2a) in acetonitrile efficiently occurred to afford a photostationary mixture containing 1a and 2a in a 95:5 ratio. The photoisomerization was remarkably accelerated by bubbling air, by adding metal salt such as Mg(ClO4)2 and LiBF4, and also by aromatic hydrocarbons such as phenanthrene and biphenyl. The quantum yield for the photoisomerization of 2a to 1a exceeded unity, indicating that this photoisomerization involved a chain process. The DCA-sensitized photoisomerization of optically resolved (-)-1a afforded a racemic mixture of (+)-1a and (-)-1a. These photoreactions are initiated by a one-electron transfer from CP to the excited singlet of DCA. The photocycloaddition proceeds via radical ion pairs in solvent cage and the photoisomerization proceeds via solvent-separated radical cations of CP.

  DOI：

  10.1021/jo00032a045
• 作为产物：
  描述：

  C₃₁H₃₂ 以 甲醇 为溶剂， 生成 cis-1,2-di(4-methylphenyl)cyclopropane
  参考文献：
  名称：

  .pi.-Interaction photochemistry. Relation between photochemical reaction in tetraphenylalkanes and the separation of interaction .pi. systems

  摘要：

  DOI：

  10.1021/ja00780a018

文献信息

• (2σ + 4π) Photocycloaddition of 1,2-diarylcyclopropanes to 9,10-dicyanoamthracene via geminate radical ion pair
  作者：Nobuyuki Ichinose、Kazuhiko Mizuno、Ziro Hiromoto、Yoshio Otsuji

  DOI：10.1016/s0040-4039(00)85282-x

  日期：1986.1

  Irradiation of a degassed acetonitrile solution containing 9,10-dicyanoanthracene (DCA) and 1,2-diarylcyclopropanes gave (2σ + 4π) photocycloadducts in good yields. The geminate radical ion pairs between DCA and the cyclopropanes are involved as key intermediates in this photoreaction.

  含有9,10-二氰基蒽（DCA）和1,2-二芳基环丙烷的脱气乙腈溶液的辐照可得到高收率的（2σ+4π）光环加合物。DCA和环丙烷之间的双联自由基离子对是该光反应的关键中间体。
• Bondarenko, O. B.; Buevich, A. V.; Voevodskaya, T. I., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 9, p. 1746 - 1753
  作者：Bondarenko, O. B.、Buevich, A. V.、Voevodskaya, T. I.、Saginova, L. G.、Shabarov, Yu. S.

  DOI：——

  日期：——
• BONDARENKO, O. B.;BUEVICH, A. V.;VOEVODSKAYA, T. I.;SAGINOVA, L. G.;SHABA+, ZH. ORGAN. XIMII, 24,(1988) N 9, S. 1937-1944
  作者：BONDARENKO, O. B.、BUEVICH, A. V.、VOEVODSKAYA, T. I.、SAGINOVA, L. G.、SHABA+

  DOI：——

  日期：——