cis-dibenzobicyclo<3.3.0>octa-2,7-diene | 14090-18-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: cis-dibenzobicyclo<3.3.0>octa-2,7-diene
• 英文别名: cis-4b,9,9a,10-Tetrahydro-indeno<1.2-a>inden；cis-4b,9,9a,10-Tetrahydro-indeno[1.2-a]inden
• CAS: 14090-18-7
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: MFRCOLSGEFIEPG-AKAXFMLLSA-N

物化性质

• 沸点：
  325.0±32.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 氯化亚砜 、 氢气 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 cis-dibenzobicyclo<3.3.0>octa-2,7-diene
  参考文献：
  名称：

  Bridged Polycyclic Compounds. XLIV. Stereochemistry of Cyclopropane Ring Formation from Substituted Dibenzobicyclo[3.2.1]octadienes

  摘要：

  DOI：

  10.1021/ja00978a041

文献信息

• 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.
• Free-radical additions to dibenzotricyclo[3.3.0.02,8]-3,6-octadiene
  作者：Bruce B. Jarvis

  DOI：10.1021/jo00829a011

  日期：1970.4
• Crystal and molecular structure ofcis-dibenzobicyclo[3.3.0]octa-2,7-diene, C16H14
  作者：J. M. M. Smits、J. H. Noordik、Paul T. Beurskens、W. H. Laarhoven、F. A. T. Lijten

  DOI：10.1007/bf01566043

  日期：1986.2
• 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
• Bridged polycyclic compounds. LXIV. Stereochemistry of reagent-promoted 1,3-eliminations
  作者：Stanley J. Cristol、Alan R. Dahl、Wendel Y. Lim

  DOI：10.1021/ja00722a021

  日期：1970.9