(3aR,4R,9S,9aS)-4,9-diphenyl-2,3,4,9-tetrahydro-1H-4,9-epoxy-3a,9a-methanocyclopenta[b]naphthalene | 137648-76-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3aR,4R,9S,9aS)-4,9-diphenyl-2,3,4,9-tetrahydro-1H-4,9-epoxy-3a,9a-methanocyclopenta[b]naphthalene
• CAS: 137648-76-1
• 化学式: C₂₆H₂₂O
• 分子量: 350.46
• InChiKey: SYSQADYKMHTMBL-FATVKVNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1,3-二苯基异苯并呋喃 、 1,5-dibromobicyclo<3.1.0>hexane 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 以63%的产率得到(3aR,4R,9S,9aS)-4,9-diphenyl-2,3,4,9-tetrahydro-1H-4,9-epoxy-3a,9a-methanocyclopenta[b]naphthalene
  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

• Bicyclo[3.1.0]hex-(1,5)-ene and bicyclo[4.1.0]hept-(1,6)-ene
  作者：Kenneth B. Wiberg、George Bonneville

  DOI：10.1016/0040-4039(82)80136-6

  日期：1982.1

  The formation and trapping of bicyclo[3.1.0]hex-(1,5)-ene and bicyclo[4.1.0]hept-(1,6)-ene from the corresponding vicinal dibromides is described.

  描述了由相应的邻位二溴化物形成和捕获双环[3.1.0] hex-（1,5）-烯和双环[4.1.0]庚基-（1,6）-烯。