(Z)-ethyl 3-(4-methyl-2-(2-phenylethynyl)phenylamino)-3-phenylacrylate | 1373169-61-9

• 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-methyl-2-(2-phenylethynyl)phenylamino)-3-phenylacrylate
• 英文别名: (Z)-ethyl 3-(4-methyl-2-(phenylethynyl)phenylamino)-3-phenylacrylate
• CAS: 1373169-61-9
• 化学式: C₂₆H₂₃NO₂
• 分子量: 381.474
• InChiKey: VXKYIYKALQDJBC-PLRJNAJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-methyl-2-(2-phenylethynyl)phenylamino)-3-phenylacrylate 在 1,10-菲罗啉 、 copper(I) bromide dimethylsulfide complex 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 以85%的产率得到ethyl 4-benzoyl-6-methyl-2-phenylquinoline-3-carboxylate
  参考文献：
  名称：

  Copper-Catalyzed Aerobic Intramolecular Carbo- and Amino-Oxygenation of Alkynes for Synthesis of Azaheterocycles

  摘要：

  A synthetic method of highly substituted quinolines has been developed from N-(2-alkynylaryl)enamine carboxylates under Cu-catalyzed aerobic conditions via intramolecular carbo-oxygenation of alkynes. This strategy was further applied for N-alkynylamidines for amino-oxygenation of alkynes, leading to imidazole and quinazoline derivatives.

  DOI：

  10.1021/ol3007106
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 copper(II) nitrate trihydrate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (Z)-ethyl 3-(4-methyl-2-(2-phenylethynyl)phenylamino)-3-phenylacrylate
  参考文献：
  名称：

  Copper-Catalyzed Aerobic Intramolecular Carbo- and Amino-Oxygenation of Alkynes for Synthesis of Azaheterocycles

  摘要：

  A synthetic method of highly substituted quinolines has been developed from N-(2-alkynylaryl)enamine carboxylates under Cu-catalyzed aerobic conditions via intramolecular carbo-oxygenation of alkynes. This strategy was further applied for N-alkynylamidines for amino-oxygenation of alkynes, leading to imidazole and quinazoline derivatives.

  DOI：

  10.1021/ol3007106

文献信息

• Dearomatization Strategy of β-Enamino Ester: Construction of Indenoazepines via Tandem Michael Addition/Polycyclization
  作者：Min Yang、Jie Tang、Renhua Fan

  DOI：10.1021/ol401553n

  日期：2013.7.5

  A dearomatization strategy of beta-enamino esters was developed to construct indenoazepine derivatives. The oxidative dearomatization was combined with a base-promoted tandem Michael addition/polycyclization and an acid-catalyzed aromatization. The nonaromatic structure of the Michael adducts might be essential to the realization of the 7-endo-dig cyclization.