(E)-1-bromo-3-chloroprop-1-ene | 37675-31-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-1-bromo-3-chloroprop-1-ene
• 英文别名: 1t-bromo-3-chloro-propene；(E)-1-Brom-3-chlor-propen；1t-Brom-3-chlor-propen；1-bromo-3-chloropropene；trans-1-Brom-3-chlorpropen-1
• CAS: 37675-31-3
• 化学式: C₃H₄BrCl
• 分子量: 155.422
• InChiKey: XSESUBJBCQPSAT-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-1-bromo-3-chloroprop-1-ene 在 三氯硅烷 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 生成 [(E)-3-bromoprop-2-enyl]-trichlorosilane
  参考文献：
  名称：

  Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes

  摘要：

  Isomerically pure trans- and cis-gamma-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti- and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (<= 50% ee) has been attained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.026
• 作为产物：
  描述：

  cis-1-Brom-3-chlorpropen-1 生成 (E)-1-bromo-3-chloroprop-1-ene
  参考文献：
  名称：

  Allylic Chlorides. XX. Preparation and Properties of the 1-Bromo-3-chloro-1-propenes¹

  摘要：

  DOI：

  10.1021/ja01119a066

文献信息

• 3-Chloro-1-lithiopropene, a Functional Organolithium Reagent, and Its Reactions with Alkylboronates To Give 3-Alkylprop-1-en-3-ols
  作者：Keith Smith、Mark C. Elliott、D. Heulyn Jones

  DOI：10.1021/jo4018028

  日期：2013.9.20

  on oxidation give 3-alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic, and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.

  试剂3-氯-1-硫代丙烯( 4 )可以通过用t -BuLi处理1-溴-3-氯丙烯来产生。它是不稳定的，但如果在烷基硼酸酯（例如3 ）存在下在低温下生成，则会原位捕获重排产物2，其在氧化时以良好的产率得到 3-烷基丙-1-烯-3-醇。该反应适用于伯、仲、苄基甚至叔烷基硼酸酯，提供带有几乎任何使用有机硼烷化学可获得的烷基并结合这些基团的所有特征的烯丙醇。
• Allylic Chlorides. XX. Preparation and Properties of the 1-Bromo-3-chloro-1-propenes¹
  作者：Lewis F. Hatch、Kenneth E. Harwell

  DOI：10.1021/ja01119a066

  日期：1953.12
• Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes
  作者：Andrei V. Malkov、Claire MacDonald、Pavel Kočovský

  DOI：10.1016/j.tetasy.2010.03.026

  日期：2010.5

  Isomerically pure trans- and cis-gamma-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti- and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (<= 50% ee) has been attained. (C) 2010 Elsevier Ltd. All rights reserved.
• cis-trans Isomerization of 1-Bromo-1-propene and Related Compounds
  作者：Kenneth E. Harwell、Lewis F. Hatch

  DOI：10.1021/ja01611a088

  日期：1955.3

表征谱图