1-chloro-3-cyano-1-phenylpropan-2-yl acetate | 1069111-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-chloro-3-cyano-1-phenylpropan-2-yl acetate
• CAS: 1069111-42-7
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: ONPRCECDOBERIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-chloro-3-cyano-1-phenylpropan-2-yl acetate 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 cis-4-Phenyl-3-butennitril 、 (E)-4-苯基-3-丁烯腈
  参考文献：
  名称：

  General, Stereoselective Synthesis of (Z)-β,γ-Unsaturated Nitriles Promoted by Samarium Diiodide

  摘要：

  A method to obtain (Z)-beta,gamma-unsaturated nitriles in high or good yields and with moderate or high stereoselectivity is described. The products were achieved through the photoinduced metalation of 3-acetoxy-4-chloronitriles with Sml(2). The starting compounds were readily prepared, and a mechanism is proposed to explain this stereoselective beta-elimination reaction.

  DOI：

  10.1021/ol801752m
• 作为产物：
  描述：

  4-chloro-3-hydroxy-4-phenylbutanenitrile 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 生成 1-chloro-3-cyano-1-phenylpropan-2-yl acetate
  参考文献：
  名称：

  General, Stereoselective Synthesis of (Z)-β,γ-Unsaturated Nitriles Promoted by Samarium Diiodide

  摘要：

  A method to obtain (Z)-beta,gamma-unsaturated nitriles in high or good yields and with moderate or high stereoselectivity is described. The products were achieved through the photoinduced metalation of 3-acetoxy-4-chloronitriles with Sml(2). The starting compounds were readily prepared, and a mechanism is proposed to explain this stereoselective beta-elimination reaction.

  DOI：

  10.1021/ol801752m