3-(dichloromethyl)-1,1'-bisbicyclo<1.1.1>pentane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 3-(dichloromethyl)-1,1'-bisbicyclo<1.1.1>pentane
• 英文别名: 1-(1-bicyclo[1.1.1]pentanyl)-3-(dichloromethyl)bicyclo[1.1.1]pentane
• 化学式: C₁₁H₁₄Cl₂
• 分子量: 217.138
• InChiKey: LSRMLOKVMRUYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  [1.1.1]螺桨烷 以4%的产率得到
  参考文献：
  名称：

  Bunz Uwe, Herpich Walter, Podlech Joachim, Polborn Kurt, Pratzel Angelika+, J. Amer. Chem. Soc., 116 (1994) N 17, S 7637-7641

  摘要：

  DOI：

文献信息

• Reaction of 1-(Halomethyl)bicyclo[1.1.1]pentanes with Strong Bases: Evidence for a Carbene-Bridgehead Olefin-Carbene Rearrangement
  作者：Uwe Bunz、Walter Herpich、Joachim Podlech、Kurt Polborn、Angelika Pratzel、David S. Stephenson、Guenter Szeimies

  DOI：10.1021/ja00096a021

  日期：1994.8

  The reaction of 1-(dichloromethyl)bicyclo[1.1.1]pentane (10a) with MeLi afforded 1-chloro-2-methylbicyclo-[2.1.1]hexane (14) and 1,2-dichloro-2-methylbicyclo[2.1.1]hexane (15) in yields of 15 and 11%. 1-(Trichloromethyl)bicyclo[1.1.1]pentane (10b) and MeLi led to a 62% yield of 15. [C-12]-Labeling of the trichloromethyl group (10e) showed that the label was exclusively found in the C-1 position of 15, indicating an overall two CC bond breaking and two CC bond forming process. Treatment of 10b, 10c, and 10d with MeLi or NaN(SiMe(3))(2) in the presence of 2,5-dimethylfuran, cyclohexene, and tetramethylethylene, respectively, gave rise to spiroadducts 24a, 25, and 27, respectively, in yields of 29, 10, and 10%. The last two reactions were accompanied by the formation of trihalides 26 (16%) and 28 (25%). 10d, NaN(SiMe(3))(2), and triethylsilane produced a 34% yield of silane 29, The results are interpreted on the basis of a carbene (19) --> bridgehead olefin (20) --> carbene (21) rearrangement.
• Bunz Uwe, Herpich Walter, Podlech Joachim, Polborn Kurt, Pratzel Angelika+, J. Amer. Chem. Soc., 116 (1994) N 17, S 7637-7641
  作者：Bunz Uwe, Herpich Walter, Podlech Joachim, Polborn Kurt, Pratzel Angelika+

  DOI：——

  日期：——