trans-bicyclo<4.2.0>octane | 63296-41-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: trans-bicyclo<4.2.0>octane
• 英文别名: (1R,6R)-bicyclo[4.2.0]octane
• CAS: 63296-41-3
• 化学式: C₈H₁₄
• 分子量: 110.199
• InChiKey: RPZUBXWEQBPUJR-HTQZYQBOSA-N

物化性质

• 沸点：
  <160 °C
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,7-辛二烯 在 bis(triphenylphosphine)ethylenenickel(0) 氧气 作用下， 反应 26.0h， 以21%的产率得到trans-bicyclo<4.2.0>octane
  参考文献：
  名称：

  由镍络合物诱导的不饱和化合物的立体特异性光二聚化

  摘要：

  辐照（乙烯）双（三苯基膦）镍 (1) 或双（三苯基膦）镍环戊烷诱导取代烯烃（如丙烯腈和丙烯酸甲酯）的立体有择环二聚反应，提供反式 1,2-二取代环丁烷，而 1,7-辛二烯转化为反式-双环[4.2.0]辛烷。乙烯被光化学二聚化为由 1 诱导的环状和线性二聚体。

  DOI：

  10.1246/cl.1985.1235

文献信息

• Investigations into the Mechanism of Inter- and Intramolecular Iron-Catalyzed [2 + 2] Cycloaddition of Alkenes
  作者：Matthew V. Joannou、Jordan M. Hoyt、Paul J. Chirik

  DOI：10.1021/jacs.0c00250

  日期：2020.3.18

  catalytically relevant intermediates were used to gain insight into the mechanism of both inter- and intramolecular [2+2] cycloaddition reactions. For the stereo- and regioselective [2+2] cycloaddition of 1-octene to form trans-1,2-dihexylcyclobutane, a first-order dependence on both iron complex and alkene was measured as well as an inverse dependence on N2 pressure. Both 57Fe Mössbauer and infrared spectroscopic

  报道了由 (tricPDI)Fe(N2) (tricPDI = 2,6-(2,4,6-三环戊基)C6H2N=CMe)2C5H3N 促进的分子间和分子内 [2+2] 烯烃环加成形成环丁烷的机理研究）。结合动力学测量、冷冻淬火 57Fe Mössbauer 和红外光谱测量、氘标记研究、自然丰度 13C KIE 研究以及催化相关中间体的分离和表征，以深入了解分子间和分子内的机制 [2 +2] 环加成反应。对于 1-辛烯的立体和区域选择性 [2+2] 环加成形成反式-1,2-二己基环丁烷，测量了对铁配合物和烯烃的一级依赖性以及对 N2 压力的逆向依赖性。57Fe Mössbauer 和红外光谱测量均将 (tricPDI)Fe(N2)(η2-1-辛烯) 确定为催化剂静止状态。1-辛烯与 (tricPDI)Fe(η2-1-辛烯) 的决定速率关联解释了烯烃的一级依赖性和对 N2 的反向依赖性。重原子 13C/12C
• Samuel, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1989, p. 1259 - 1265
  作者：Samuel, Christopher J.

  DOI：——

  日期：——
• Ring distortion effect on δ13C values of bicyclo[4.n.0] alkanes
  作者：P. Metzger、C. Cabestaing、E. Casadevall、A. Casadevall

  DOI：10.1002/mrc.1270190307

  日期：1982.7

  AbstractThe 13C NMR spectra of trans‐ and cis‐fused bicyclo[4.n.0]alkanes, where n=4, 3 and 2, were determined. The distortion of the six membered ring, which is due to the strain arising from the 1,2 fusion of cyclohexane with a smaller ring, is apparent mainly for the chemical shifts of the ring junction carbons. Both for the trans‐and for the cis‐fused hydrocarbons the results support a cyclohexane in a chair conformation, distorted to a different degree according to the size of the other ring. The geometries of the different compounds in the series were calculated.
• SAMUEL, CHRISTOPHER J., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1259-1265
  作者：SAMUEL, CHRISTOPHER J.

  DOI：——

  日期：——
• STEREOSPECIFIC PHOTODIMERIZATION OF UNSATURATED COMPOUNDS INDUCED BY NICKEL COMPLEXES
  作者：Akira Miyashita、Shohgo Ikezu、Hiroyuki Nohira

  DOI：10.1246/cl.1985.1235

  日期：1985.8.5

  (1) or bis(triphenylphosphine)nickelacyclopentane induced stereospecific cyclodimerization of substituted olefins such as acrylonitrile and methylacrylate affording trans-1,2-disubstituted cyclobutanes, while 1,7-octadiene was converted to trans-bicyclo[4.2.0]octane. Ethylene was photochemically dimerized to cyclo- and linear dimers induced by 1.

  辐照（乙烯）双（三苯基膦）镍 (1) 或双（三苯基膦）镍环戊烷诱导取代烯烃（如丙烯腈和丙烯酸甲酯）的立体有择环二聚反应，提供反式 1,2-二取代环丁烷，而 1,7-辛二烯转化为反式-双环[4.2.0]辛烷。乙烯被光化学二聚化为由 1 诱导的环状和线性二聚体。

表征谱图