(Z)-ethyl 3-(4-chlorophenyl)-3-(3-phenylprop-2-ynylamino)acrylate | 1325714-28-0

• 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-(3-phenylprop-2-ynylamino)acrylate
• CAS: 1325714-28-0
• 化学式: C₂₀H₁₈ClNO₂
• 分子量: 339.821
• InChiKey: DHCSNXSGDSRJPH-CYVLTUHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-(3-phenylprop-2-ynylamino)acrylate 在 三乙烯二胺 、 氧气 、 copper dichloride 作用下， 以 二甲基亚砜 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 以54%的产率得到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 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (Z)-ethyl 3-(4-chlorophenyl)-3-(3-phenylprop-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

文献信息

• Metal‐Free Oxidative [5+1] Cyclization of 1,5‐Enynes for the Synthesis of Pyrazine 1‐Oxide
  作者：Xiao‐Feng Xia、Mingming Zhao、Wei He、Lianghua Zou、Xinxin San、Dawei Wang

  DOI：10.1002/adsc.202000756

  日期：2020.9.8

  A chemo‐selective nitrosylation of 1,5‐enynes via a sequence of NO radical incorporation and intramolecular radical cyclization was reported. The formation of two C−N bonds and one C−O bond make this [5+1] cycloaddition reaction an efficient approach to synthesize pyrazine 1‐oxides in moderate to good yields. Metal‐free, short reaction time and mild conditions render this strategy more practical, eco‐friendly

  据报道，通过一系列的NO自由基结合和分子内自由基环化反应，实现了1,5-烯类的化学选择性亚硝基化。两个C–N键和一个C–O键的形成使此[5 + 1]环加成反应成为一种以中等到良好的产率合成吡嗪1-氧化物的有效方法。无金属，短反应时间和温和条件使该策略更加实用，生态友好和方便。该协议的合成效用突出了支架的多样化。