(Z)-ethyl 3-(4-chlorophenyl)-3-(prop-2-ynylamino)acrylate | 1325714-39-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 3-(4-chlorophenyl)-3-(prop-2-ynylamino)acrylate
• CAS: 1325714-39-3
• 化学式: C₁₄H₁₄ClNO₂
• 分子量: 263.724
• InChiKey: SQHIGEQJYAGMLD-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-(4-chlorophenyl)-3-(prop-2-ynylamino)acrylate 在 三乙烯二胺 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氧气 、 三乙胺 、 copper dichloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 生成 ethyl 4-benzoyl-2-(4-chlorophenyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Copper-Mediated Aerobic Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles from N-Allyl/Propargyl Enamine Carboxylates

  摘要：

  Synthetic methods for 3-azabicyclo[3.1.0] hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O-2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.

  DOI：

  10.1021/ja206580j
• 作为产物：
  描述：

  (4-氯苯基)-丙酸乙酯 、 炔丙胺 以 乙醇 为溶剂， 以66%的产率得到(Z)-ethyl 3-(4-chlorophenyl)-3-(prop-2-ynylamino)acrylate
  参考文献：
  名称：

  Copper-Mediated Aerobic Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles from N-Allyl/Propargyl Enamine Carboxylates

  摘要：

  Synthetic methods for 3-azabicyclo[3.1.0] hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O-2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.

  DOI：

  10.1021/ja206580j