1-bromo-2,2-dichlorocyclopropane | 40745-72-0

• 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: 1-bromo-2,2-dichlorocyclopropane
• 英文别名: 1,1-dichloro-2-bromocyclopropane；1,1-Dichlor-2-brom-cyclopropan；1-Brom-2,2-dichlor-cyclopropan；2-Brom-1,1-dichlorcyclopropan；2-Bromo-1,1-dichlorocyclopropane
• CAS: 40745-72-0
• 化学式: C₃H₃BrCl₂
• 分子量: 189.867
• InChiKey: XNHGDEYPUNAQJA-UHFFFAOYSA-N

物化性质

• 沸点：
  171.5±35.0 °C(Predicted)
• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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-bromo-2,2-dichlorocyclopropane 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 以57%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：

  溴乙烯 、 氯仿 在 N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium dibromide 氢氧化钾 作用下， 以 水 为溶剂， 反应 48.0h， 生成 1-bromo-2,2-dichlorocyclopropane
  参考文献：
  名称：

  Cyclopropane precursors of ethylene response inhibitors in plants

  摘要：

  公开号：

  EP1388529B1

文献信息

• 1-bromo-2-chlorocyclopropene--A new cycloproparene synthon. Synthesis of 1H-Cyclopropa[b]phenanthrene
  作者：W.E. Billups、Long-Jin Lin、Benny E. Arney、Wayne A. Rodin、Edward W. Casserly

  DOI：10.1016/0040-4039(84)80034-9

  日期：——

  Treatment of 1-bromo-2,2-dichloro(trimethylsilyl)cyclopropane (2) with tetra-n-butylammonium fluoride in tetrahydrofuran yields 1-bromo-2-chlorocyclopropene (1). 1H-Cyclopropa[b]phenanthrene (3) can be prepared by aromatization of the Diels-Alder adduct of 1 and 1,2-dimethylene-3,5,6,7,8,9-hexahydronaphthalene (6) using DDQ followed by potassium t-butoxide in tetrahydrofuran.

  用氟化四正丁基铵在四氢呋喃中处理1-溴-2,2-二氯（三甲基甲硅烷基）环丙烷（2），得到1-溴-2-氯环丙烯（1）。1H-环丙烷[b]菲（3）可以通过使用DDQ然后将1和1,2-二亚甲基-3,5,6,7,8,9-六氢萘的Diels-Alder加合物芳构化而制得四氢呋喃中的叔丁醇钾。
• BILLUPS, W. E.;LIN, LONG-JIN;ARNEY, B. E. ,, JR.;RODIN, W. A.;CASSERLY, E+, TETRAHEDRON LETT., 1984, 25, N 36, 3935-3938
  作者：BILLUPS, W. E.、LIN, LONG-JIN、ARNEY, B. E. ,, JR.、RODIN, W. A.、CASSERLY, E+

  DOI：——

  日期：——
• 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.
• 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

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