1,1,2-tribromocyclopropane | 178425-55-3

• 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-tribromocyclopropane
• 英文别名: tribromocyclopropane
• CAS: 178425-55-3
• 化学式: C₃H₃Br₃
• 分子量: 278.769
• InChiKey: VTKNAATZEMZZPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  6
• 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-tribromocyclopropane 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到丙醛二乙基乙缩醛
  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
• 作为产物：
  描述：

  2,2-二溴环丙烷-1-羧酸 在 溴 、 mercury(II) oxide 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以75%的产率得到1,1,2-tribromocyclopropane
  参考文献：
  名称：

  摘要：

  Cyclopent-2-en-1-one is a versatile electrophilic cyclopentadiene equivalent in reactions with 1-bromo-1-lithiocyclopropanes. The synthetic sequence (outlined in Scheme 1) has been applied to the synthesis of functionalized 7-X-7,8-dihydrocalicenes 13c (Scheme 3) and 13d (Scheme 4). 7-Bromo-7,8-dihydrocalicene (13d) is considered to be a promising precursor of the so far unknown parent calicene (2). A similar sequence has been realized for 7-(chloromethyl)-7,8-dihydrocalicene (21a, Scheme 5) which, under appropriate conditions, could give 7-methylcalicene (16).

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<571::aid-hlca571>3.0.co;2-m

文献信息

• Cyclopropane precursors of ethylene response inhibitors in plants
  申请人：ROHM AND HAAS COMPANY

  公开号：EP1388529B1

  公开（公告）日：2014-07-16
• 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.
• ——
  作者：Ahmad Al-Dulayymi、Xiaoming Li、Markus Neuenschwander

  DOI：10.1002/(sici)1522-2675(20000315)83:3<571::aid-hlca571>3.0.co;2-m

  日期：2000.3.15

  Cyclopent-2-en-1-one is a versatile electrophilic cyclopentadiene equivalent in reactions with 1-bromo-1-lithiocyclopropanes. The synthetic sequence (outlined in Scheme 1) has been applied to the synthesis of functionalized 7-X-7,8-dihydrocalicenes 13c (Scheme 3) and 13d (Scheme 4). 7-Bromo-7,8-dihydrocalicene (13d) is considered to be a promising precursor of the so far unknown parent calicene (2). A similar sequence has been realized for 7-(chloromethyl)-7,8-dihydrocalicene (21a, Scheme 5) which, under appropriate conditions, could give 7-methylcalicene (16).