7'-bicyclo<4.1.0>heptylidenecyclopentane | 140705-69-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 7'-bicyclo<4.1.0>heptylidenecyclopentane
• 英文别名: Bwhtyiqorhhvcd-uhfffaoysa-；7-cyclopentylidenebicyclo[4.1.0]heptane
• CAS: 140705-69-7
• 化学式: C₁₂H₁₈
• 分子量: 162.275
• InChiKey: BWHTYIQORHHVCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  对甲苯磺酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 7'-bicyclo<4.1.0>heptylidenecyclopentane
  参考文献：
  名称：

  Generation of Cycloalkylidene Carbenes via Exo-Type Cyclization of Alkynyllithiums Bearing Remote Leaving Group

  摘要：

  The reaction of 5-hexynyl tosylate (3a) with alkynyllithium (RC=CLi; R Ph, TMS) gives enynes 5 and 6. The reaction proceeds through a mechanism involving a novel exo-type cyclization of 6-lithiod-hexynyl tosylate to form cyclopentylidene carbene. Enyne 6 is produced by the addition of RC=CLi to the carbene, whereas rearrangement of the carbene to cyclohexyne followed by carbolithiation with RC=CLi gives enyne 5. The formation of cyclopentylidene carbene and cyclohexyne as intermediates is clearly demonstrated by trapping experiments with cyclohexene land triethylsilane) and with 1,3-diphenylisobenzofuran, respectively. Alkynyllithiums derived from 3-butynyl and 6-heptynyl p-fluorobenzenesulfonates (19a,b) undergo a similar exo-type cyclization to give cyclopropylidene and cyclohexylidene carbenes, respectively.

  DOI：

  10.1021/jo981411p

文献信息

• A new preparation of methylenecyclopropanes utilizing trimethylsilyldiazomethane
  作者：Atsushi Sakai、Toyohiko Aoyama、Takayuki Shioiri

  DOI：10.1016/s0040-4020(98)01176-4

  日期：1999.3

  Reactions of aliphatic ketones with lithium trimethylsilyl-diazomethane in the presence of excess olefins afforded methylenecyclopropanes in moderate to good yields. The multiplicity of the alkylidene carbene intermediate in the reacting state has been revealed to be a singlet.

  在过量烯烃的存在下，脂肪族酮与三甲基甲硅烷基重氮甲烷锂的反应以中等至良好的产率提供了亚甲基环丙烷。已经发现处于反应状态的亚烷基卡宾中间体的多样性是单重态。
• Xu, Linxiao; Lin, Guoying; Tao, Fenggang, Acta Chemica Scandinavica, 1992, vol. 46, # 7, p. 650 - 653
  作者：Xu, Linxiao、Lin, Guoying、Tao, Fenggang、Brinker, Udo H.

  DOI：——

  日期：——
• Generation of Cycloalkylidene Carbenes via Exo-Type Cyclization of Alkynyllithiums Bearing Remote Leaving Group
  作者：Toshiro Harada、Katsuhiro Iwazaki、Takeshi Otani、Akira Oku

  DOI：10.1021/jo981411p

  日期：1998.11.1

  The reaction of 5-hexynyl tosylate (3a) with alkynyllithium (RC=CLi; R Ph, TMS) gives enynes 5 and 6. The reaction proceeds through a mechanism involving a novel exo-type cyclization of 6-lithiod-hexynyl tosylate to form cyclopentylidene carbene. Enyne 6 is produced by the addition of RC=CLi to the carbene, whereas rearrangement of the carbene to cyclohexyne followed by carbolithiation with RC=CLi gives enyne 5. The formation of cyclopentylidene carbene and cyclohexyne as intermediates is clearly demonstrated by trapping experiments with cyclohexene land triethylsilane) and with 1,3-diphenylisobenzofuran, respectively. Alkynyllithiums derived from 3-butynyl and 6-heptynyl p-fluorobenzenesulfonates (19a,b) undergo a similar exo-type cyclization to give cyclopropylidene and cyclohexylidene carbenes, respectively.