1-(trimethylsilyl)-7,7-dichlorobicyclo<4.1.0>heptane | 58660-83-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 1-(trimethylsilyl)-7,7-dichlorobicyclo<4.1.0>heptane
• 英文别名: 7,7-Dichlor-1-trimethylsilylbicyclo-<4,1,0>-heptan；7,7-Dichlor-1-trimethylsilylbicyclo-[4,1,0]-heptan；(7,7-Dichlorobicyclo[4.1.0]heptan-1-yl)(trimethyl)silane；(7,7-dichloro-1-bicyclo[4.1.0]heptanyl)-trimethylsilane
• CAS: 58660-83-6
• 化学式: C₁₀H₁₈Cl₂Si
• 分子量: 237.244
• InChiKey: UQIOWUIERQRHBA-UHFFFAOYSA-N

物化性质

• 沸点：
  254.8±30.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  13
• 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

• 作为反应物：
  描述：

  1-(trimethylsilyl)-7,7-dichlorobicyclo<4.1.0>heptane 在 四丁基氟化铵 作用下， 生成 2-chlorocy-1,3-cloheptadiene
  参考文献：
  名称：

  1,3-Bridged cyclopropenes

  摘要：

  Solid fluoride deposited on glass helices has been used to effect the gas-phase elimination of 1-(trimethylsilyl)-7-chlorobicyclo[4.1.0]heptane and 1-(trimethylsilyl)-8-chlorobicyclo[5.1.0]octane to yield bicyclo[4.1.0]hept-1(7)-ene and bicyclo[5.1.0]oct-1(8)-ene, respectively. Bicyclo[4.1.0]hept-1(7)-ene dimerizes below ca. -90-degrees-C via an ene reaction to yield a new cyclopropene, which then couples to form tetramers. The structures of two tricyclohexane tetramers were determined by X-ray crystallography. The ene dimer was found to react with molecular oxygen to yield two carbonyl compounds identified as 2-(1-bicyclo[4.1.0]heptyl)cyclohexene-1-carboxaldehyde and 3-(1-bicyclo[4.1.0]heptyl)cyclohept-2-en-1-one. These compounds are thought to result from the reaction of molecular oxygen with carbenes that would arise from cyclopropene-vinylcarbene rearrangements. Bicyclo[5.1.0]oct-1(8)-ene is considerably more stable than its lower homologue but also dimerizes via an ene reaction. 7-Chlorobicyclo[4.1.0]hept-1(7)-ene rearranges below -90-degrees-C to yield 2-chloro-1,3-cycloheptadiene.

  DOI：

  10.1021/ja00021a025

文献信息

• Organosilicon-directed substitution reaction on bicyclic -dihalocyclopropanes. A facile formation of bicyclo[4.1.0]heptan-7-one dialkyl acetals
  作者：Takashi Ishihara、Tadashi Kudaka、Teiichi Ando

  DOI：10.1016/s0040-4039(01)81513-6

  日期：——
• ISHIHARA, TAKASHI;KUDAKA, TADASHI;ANDO, TEIICHI, TETRAHEDRON LETT., 1984, 25, N 42, 4765-4766
  作者：ISHIHARA, TAKASHI、KUDAKA, TADASHI、ANDO, TEIICHI

  DOI：——

  日期：——
• 1,3-Bridged cyclopropenes
  作者：W. E. Billups、Gon Ann Lee、Benny E. Arney、Kenton H. Whitmire

  DOI：10.1021/ja00021a025

  日期：1991.10

  Solid fluoride deposited on glass helices has been used to effect the gas-phase elimination of 1-(trimethylsilyl)-7-chlorobicyclo[4.1.0]heptane and 1-(trimethylsilyl)-8-chlorobicyclo[5.1.0]octane to yield bicyclo[4.1.0]hept-1(7)-ene and bicyclo[5.1.0]oct-1(8)-ene, respectively. Bicyclo[4.1.0]hept-1(7)-ene dimerizes below ca. -90-degrees-C via an ene reaction to yield a new cyclopropene, which then couples to form tetramers. The structures of two tricyclohexane tetramers were determined by X-ray crystallography. The ene dimer was found to react with molecular oxygen to yield two carbonyl compounds identified as 2-(1-bicyclo[4.1.0]heptyl)cyclohexene-1-carboxaldehyde and 3-(1-bicyclo[4.1.0]heptyl)cyclohept-2-en-1-one. These compounds are thought to result from the reaction of molecular oxygen with carbenes that would arise from cyclopropene-vinylcarbene rearrangements. Bicyclo[5.1.0]oct-1(8)-ene is considerably more stable than its lower homologue but also dimerizes via an ene reaction. 7-Chlorobicyclo[4.1.0]hept-1(7)-ene rearranges below -90-degrees-C to yield 2-chloro-1,3-cycloheptadiene.