1-(trichloro<12C>methyl)<3-D>bicyclo<1.1.1>pentane | 105542-95-8

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 1-(trichloro<12C>methyl)<3-D>bicyclo<1.1.1>pentane
• 英文别名: 1-deutero-3-(trichloromethyl)bicyclo<1.1.1>pentane；1-deutero-3-(trichloromethyl)bicyclo[1.1.1]pentane；1-deuterio-3-(trichloromethyl)bicyclo[1.1.1]pentane
• CAS: 105542-95-8
• 化学式: C₆H₇Cl₃
• 分子量: 186.473
• InChiKey: BOEAPFRTYJQXEH-QYKNYGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  1-(trichloro<12C>methyl)<3-D>bicyclo<1.1.1>pentane 以59%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：
• 作为产物：
  描述：

  [1.1.1]螺桨烷 以13%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

• Reactions of [1.1.1]propellane
  作者：Kenneth B. Wiberg、Sherman T. Waddell

  DOI：10.1021/ja00162a022

  日期：1990.3

  The free radical addition reactions of [1.1.1] propellane (1) are described in some detail and allowed the preparation of a wide variety of 1,3-disubstituted bicyclo [1.1.1.] pentanes. The reaction of 1 with free radicals was more rapid than that of bicyclo [1.1.0] butane (2), whereas bicyclo [2.1.0] pentane (3) was relatively inert

  [1.1.1] 推进烷 (1) 的自由基加成反应进行了一些详细的描述，并允许制备各种 1,3-二取代双环 [1.1.1.] 戊烷。1 与自由基的反应比双环 [1.1.0] 丁烷 (2) 更快，而双环 [2.1.0] 戊烷 (3) 相对惰性
• [1.1.1]Propellane: Reaction with free radicals
  作者：Kenneth B. Wiberg、Shennan T. Waddell、Keith Laidig

  DOI：10.1016/s0040-4039(00)84310-5

  日期：1986.1

  [1.1.1]Propellane is more reactive towards free radicals than bicyclo[1.1.0]butane, and much more reactive than bicyclo[2.1.0]pentane. Therefore, the reactivity is not determined by strain energy relief or the HOMO energy. The addition of acetaldehyde is unique in that a 1:2 adduct is formed. A number of other additions are described, and provide convenient routes to 1,3-disubstituted bicyclo[1.1.1]pentanes

  [1.1.1]螺旋桨比双环[1.1.0]丁烷对自由基的反应性更高，并且比双环[2.1.0]戊烷更具反应性。因此，反应性不是由应变能释放或HOMO能决定的。乙醛的添加是独特的，因为会形成1：2的加合物。描述了许多其他的加成，并提供了通往1，3-二取代的双环[1.1.1]戊烷的便利途径。
• 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.