[(Z)-5-(2,2,2-trichloroethanimidoyl)oxypent-3-enyl] acetate | 930608-34-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(Z)-5-(2,2,2-trichloroethanimidoyl)oxypent-3-enyl] acetate
• CAS: 930608-34-7
• 化学式: C₉H₁₂Cl₃NO₃
• 分子量: 288.558
• InChiKey: TXPWLDCJEMDTBA-DOSOMBFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(Z)-5-(2,2,2-trichloroethanimidoyl)oxypent-3-enyl] acetate 、 4-乙酰氧基苯酚 在 [(S)-COP-OAc]2 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以93%的产率得到(R)-3-(4-acetoxyphenoxy)pent-4-enyl acetate
  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
• 作为产物：
  描述：

  (Z)-5-hydroxypent-3-enyl acetate 、 三氯乙腈 在 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， 生成 [(Z)-5-(2,2,2-trichloroethanimidoyl)oxypent-3-enyl] acetate
  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