[(Z)-3-bromoprop-2-enyl]-trichlorosilane | 1246307-78-7

• 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: [(Z)-3-bromoprop-2-enyl]-trichlorosilane
• CAS: 1246307-78-7
• 化学式: C₃H₄BrCl₃Si
• 分子量: 254.413
• InChiKey: YRVHNFSUUFTQQS-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  8
• 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：

  [(Z)-3-bromoprop-2-enyl]-trichlorosilane 、 4-氯苯甲醛 在 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 生成
  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 在 三氯硅烷 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 生成 [(Z)-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

文献信息

• 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.