1,1,2-tribromo-3-methylcyclopropane | 212692-82-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1,1,2-tribromo-3-methylcyclopropane
• CAS: 212692-82-5
• 化学式: C₄H₅Br₃
• 分子量: 292.796
• InChiKey: RRERBWVTGAZASI-UHFFFAOYSA-N

物化性质

• 沸点：
  192.6±30.0 °C(Predicted)
• 密度：
  2.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  乙醇 、 1,1,2-tribromo-3-methylcyclopropane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 24.0h， 以65%的产率得到2-丁炔乙缩醛
  参考文献：
  名称：

  Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.

  摘要：

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.

  DOI：

  10.3891/acta.chem.scand.52-1029
• 作为产物：
  描述：

  1-溴基-1-丙烯 、 三溴甲烷 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以46%的产率得到1,1,2-tribromo-3-methylcyclopropane
  参考文献：
  名称：

  Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.

  摘要：

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.

  DOI：

  10.3891/acta.chem.scand.50-0446

文献信息

• Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.
  作者：Leiv K. Sydnes、Einar Bakstad、Morten Heide、Georg W. Jensen、Inge L. Møller、Ruby I. Nielsen、Carl Erik Olsen、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0446

  日期：——

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.
• Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.
  作者：Einar Bakstad、Leiv K. Sydnes、Anders Kjær、Salka E. Nielsen、Carl E. Olsen、Kirsi Ranta、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1029

  日期：——

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.