exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene | 85803-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene
• 英文别名: (1aS,6R,6aR)-6-phenyl-1,1a,6,6a-tetrahydrocyclopropa[a]indene
• CAS: 85803-90-3
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: RSMGRGGATLAEGP-BZUAXINKSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  323.0±17.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene 生成 3,4-二氢-1-苯基萘
  参考文献：
  名称：

  LAMBERTS, J. J. M.;LAARHOVEN, W. H., J. ORG. CHEM., 1984, 49, N 1, 100-106

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二氢-1-苯基萘 以 正己烷 为溶剂， 生成 cis-dibenzobicyclo<3.3.0>octa-2,7-diene 、 exo-4-phenylbenzobicyclo<3.1.0>hex-2-ene
  参考文献：
  名称：

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene. A simple preparation of cis-dibenzobicyclo[3.3.0]octa-2,7-diene

  摘要：

  DOI：

  10.1021/jo00217a038

文献信息

• Thermochemistry of phenyl-substituted benzobicyclo[3.1.0]hex-2-enes. Evidence for carbenes as intermediates
  作者：Joseph J. M. Lamberts、Wim H. Laarhoven

  DOI：10.1021/jo00175a020

  日期：1984.1
• Photochemistry of 1-phenyl-1,2-dihydronaphthalene in methanol
  作者：Jan Woning、Frank A. T. Lijten、Wim H. Laarhoven

  DOI：10.1021/jo00007a033

  日期：1991.3

  The photochemistry of 1-phenyl-1,2-dihydronaphthalene (1) in methanol and hexane has been investigated. The lack of influence of solvent polarity and of the presence of sulfuric acid on the rate of formation of exo-4-phenylbenzobicyclo[3.1.0]hex-2-ene (exo-2) from the primary, ring-opened photoproduct cZt-3a of 1 precludes a sudden-polarized, zwitterionic excited state from being involved in the intramolecular [4 + 2] photocycloaddition reaction leading to exo-2. The experimental results can be rationalized by assuming that this photoprocess involves a concerted pi-4a + pi-2a-type electrocyclic reaction. cis-Dibenzobicyclo[3.3.0]octa-2,7-diene (8) is proposed to arise by photocyclization of cZc-3b, followed by a thermal rearrangement. On irradiation of 1 with a broad-spectrum lamp, the ratio of the photoproducts exo-2 and 8 is correlated with the ratio of the pe and pa conformers of 1. The novel compound 1-(o-benzylphenyl)allene (6) is also formed under these conditions. Irradiation of 1 at 254 nm yields 8 as the only photoproduct. Photochemical addition of methanol was observed to complete with the photoprocess, leading to exo-2, though at a comparatively low level. A photodecomposition mode of exo-2, presumably involving heterolytic cleavage of the cyclopropane ring, presents the chief source of methoxylated photoproducts at low temperatures in methanol.
• LAMBERTS, J. J. M.;LAARHOVEN, W. H., J. ORG. CHEM., 1983, 48, N 13, 2202-2206
  作者：LAMBERTS, J. J. M.、LAARHOVEN, W. H.

  DOI：——

  日期：——
• The photochemistry of 1-phenyl-1,2-dihydronaphthalene. A simple preparation of cis-dibenzobicyclo[3.3.0]octa-2,7-diene
  作者：Wim H. Laarhoven、Frank A. T. Lijten、Jan M. M. Smits

  DOI：10.1021/jo00217a038

  日期：1985.8
• LAMBERTS, J. J. M.;LAARHOVEN, W. H., J. ORG. CHEM., 1984, 49, N 1, 100-106
  作者：LAMBERTS, J. J. M.、LAARHOVEN, W. H.

  DOI：——

  日期：——