(S)-2-(4-chlorophenoxy)but-3-enyloxy(tert-butyl)dimethylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-(4-chlorophenoxy)but-3-enyloxy(tert-butyl)dimethylsilane
• 英文别名: tert-butyl-[(2S)-2-(4-chlorophenoxy)but-3-enoxy]-dimethylsilane
• 化学式: C₁₆H₂₅ClO₂Si
• 分子量: 312.912
• InChiKey: YCQNDOATGSFSHQ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol 在 [(S)-COP-OAc]2 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (S)-2-(4-chlorophenoxy)but-3-enyloxy(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Allylic Aryl Ethers

  摘要：

  The reaction of trichloroacetimidate derivatives of (Z)-2-alken-1-ols with phenol nucleophiles in the presence of the palladium(II) catalyst [COP-OAc](2) provides 3-aryloxy-1-alkenes in high yields and high enantiomeric purity (typically 63-90% yield and 90-97% ee). The reaction is exemplified by 20 examples. The method employs 1 mol % of the commercially available catalysts (S)- or (R)-[COPOAc](2), produces the branched isomer with unprecedented regioselectivity, and is compatible with the presence of base-labile functionality in either reactant.

  DOI：

  10.1021/ol070110b

文献信息

• Catalytic Asymmetric Synthesis of Allylic Aryl Ethers
  作者：Stefan F. Kirsch、Larry E. Overman、Nicole S. White

  DOI：10.1021/ol070110b

  日期：2007.3.1

  The reaction of trichloroacetimidate derivatives of (Z)-2-alken-1-ols with phenol nucleophiles in the presence of the palladium(II) catalyst [COP-OAc](2) provides 3-aryloxy-1-alkenes in high yields and high enantiomeric purity (typically 63-90% yield and 90-97% ee). The reaction is exemplified by 20 examples. The method employs 1 mol % of the commercially available catalysts (S)- or (R)-[COPOAc](2), produces the branched isomer with unprecedented regioselectivity, and is compatible with the presence of base-labile functionality in either reactant.