(Z)-1,2-bis(2-(bicyclo[4.1.0]heptan-1-yl)cyclohex-1-en-1-yl)ethene | 135663-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1,2-bis(2-(bicyclo[4.1.0]heptan-1-yl)cyclohex-1-en-1-yl)ethene
• CAS: 135663-39-7
• 化学式: C₂₈H₄₀
• 分子量: 376.626
• InChiKey: PBPXAFBDKXHCCN-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  1,6-dicarbomethoxybicyclo<4.1.0>heptane 在 甲醇 、 氢氧化钾 、 碘苯二乙酸 、 甲基锂 、 碘 作用下， 以 甲醇 、 环己烷 为溶剂， 反应 9.5h， 生成 (Z)-1,2-bis(2-(bicyclo[4.1.0]heptan-1-yl)cyclohex-1-en-1-yl)ethene
  参考文献：
  名称：

  1,2-Bridged cyclopropenes

  摘要：

  The dehalogenations of 1,5-dihalobicyclo[3.1.0]hexanes and 1,6-dihalobicyclo[4.1.0]heptanes have been studied in solution and in the gas phase. The solution reactions led to the formation of bicyclo[3.1.0]hex-1(5)-ene and bicyclo[4.1.0]hept-1(6)-ene, respectively, but this was followed by rapid ene reactions forming dimers, which then coupled to form tetramers. The cyclopropenes could be trapped as Diels-Alder adducts. In the gas phase, with use of either potassium atoms or solid methyllithium, the products of thermal ring opening, methylenecyclopentene and methylenecyclohexene, were formed. A set of theoretical calculations was carried out dealing with the strain energies, inversion barriers, bond properties, and atom properties of bicyclo[1.1.0]but-1(3)-ene, bicyclo[2.1.0]pent-1(4)-ene, and the cyclopropenes from the experimental study. Whereas bicyclohexene and bicycloheptene appear to be fairly normal compounds except for their high strain energies, bicyclopentene may be a transition state for the carbon scrambling of methylenecyclobutylidene, and bicyclobutene has an unusual structure and charge-density distribution.

  DOI：

  10.1021/ja00021a024

文献信息

• 1,3-Bridged cyclopropenes
  作者：W. E. Billups、Gon Ann Lee、Benny E. Arney、Kenton H. Whitmire

  DOI：10.1021/ja00021a025

  日期：1991.10

  Solid fluoride deposited on glass helices has been used to effect the gas-phase elimination of 1-(trimethylsilyl)-7-chlorobicyclo[4.1.0]heptane and 1-(trimethylsilyl)-8-chlorobicyclo[5.1.0]octane to yield bicyclo[4.1.0]hept-1(7)-ene and bicyclo[5.1.0]oct-1(8)-ene, respectively. Bicyclo[4.1.0]hept-1(7)-ene dimerizes below ca. -90-degrees-C via an ene reaction to yield a new cyclopropene, which then couples to form tetramers. The structures of two tricyclohexane tetramers were determined by X-ray crystallography. The ene dimer was found to react with molecular oxygen to yield two carbonyl compounds identified as 2-(1-bicyclo[4.1.0]heptyl)cyclohexene-1-carboxaldehyde and 3-(1-bicyclo[4.1.0]heptyl)cyclohept-2-en-1-one. These compounds are thought to result from the reaction of molecular oxygen with carbenes that would arise from cyclopropene-vinylcarbene rearrangements. Bicyclo[5.1.0]oct-1(8)-ene is considerably more stable than its lower homologue but also dimerizes via an ene reaction. 7-Chlorobicyclo[4.1.0]hept-1(7)-ene rearranges below -90-degrees-C to yield 2-chloro-1,3-cycloheptadiene.