1-叔丁基双环[3.1.0]己烷 | 85739-38-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 中文名称: 1-叔丁基双环[3.1.0]己烷
• 英文名称: 1-tert-butylbicyclo<3.1.0>hexane
• 英文别名: 1-tert-butylbicyclo[3.1.0]hexane
• CAS: 85739-38-4
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: VWOWWKWGBSNQCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  10
• 可旋转键数：
  1
• 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：

  双环[3.1.0]己烷-1,5-二羧酸 在 溴 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 生成 1-叔丁基双环[3.1.0]己烷
  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

• WIBERG, K. B.;BONNEVILLE, G., TETRAHEDRON LETT., 1982, 23, N 51, 5385-5388
  作者：WIBERG, K. B.、BONNEVILLE, G.

  DOI：——

  日期：——
• 1,2-Bridged cyclopropenes
  作者：Kenneth B. Wiberg、Dean R. Artis、G. Bonneville

  DOI：10.1021/ja00021a024

  日期：1991.10

  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.