(E)-methyl 3-(2-(benzylamino)-3,5-dimethylphenyl)acrylate | 1224738-11-7

• 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: (E)-methyl 3-(2-(benzylamino)-3,5-dimethylphenyl)acrylate
• CAS: 1224738-11-7
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: XPDUPHZYHCBWFY-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• 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：

  苯硼酸酐 、 (E)-methyl 3-(2-(benzylamino)-3,5-dimethylphenyl)acrylate 在 hydroxo(1,5-cyclooctadiene)rhodium (I) dimer 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以67%的产率得到N-benzyl-3,4-dihydro-6,8-dimethyl-4-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

  摘要：

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

  DOI：

  10.1021/ol100610v
• 作为产物：
  描述：

  N-benzyl-2-bromo-4,6-dimethylaniline 、 丙烯酸甲酯（MA） 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 以41%的产率得到(E)-methyl 3-(2-(benzylamino)-3,5-dimethylphenyl)acrylate
  参考文献：
  名称：

  Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

  摘要：

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

  DOI：

  10.1021/ol100610v