(Z)-2-benzyl-3-(thiophen-3-ylmethylene)isoindolin-1-one | 1086599-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (Z)-2-benzyl-3-(thiophen-3-ylmethylene)isoindolin-1-one
• 英文别名: (3Z)-2-benzyl-3-(thiophen-3-ylmethylidene)isoindol-1-one
• CAS: 1086599-18-9
• 化学式: C₂₀H₁₅NOS
• 分子量: 317.411
• InChiKey: SYXSYSXQCPWDLL-UNOMPAQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-乙炔基噻吩 、 邻碘溴苯 、 一氧化碳 、 苄胺 在 三己基十四烷化膦溴化物 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 110.0 ℃ 、103.42 kPa 条件下， 反应 36.0h， 以73%的产率得到(Z)-2-benzyl-3-(thiophen-3-ylmethylene)isoindolin-1-one
  参考文献：
  名称：

  Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling−Carbonylation−Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids

  摘要：

  Two efficient approaches for the synthesis of isoindolin-1-one derivatives in phosphonium salt ionic liquids are described. The palladium-catalyzed carbonylation-hydroamination reaction of 1-halo-2-alkynylbenzene with amines afforded the substituted 3-methyleneisoindolin-1-ones in good yields and high selectivities in favor of the Z-isomers. The target molecules could also be synthesized by the Sonogashira coupling-carbonylation-hydroamination one-pot reaction of dihalides, alkynes, and amines. Both processes can be conducted under mild conditions and tolerate a wide array of functionalized substrates.

  DOI：

  10.1021/ol8021403

文献信息

• Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling−Carbonylation−Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids
  作者：Hong Cao、Laura McNamee、Howard Alper

  DOI：10.1021/ol8021403

  日期：2008.11.20

  Two efficient approaches for the synthesis of isoindolin-1-one derivatives in phosphonium salt ionic liquids are described. The palladium-catalyzed carbonylation-hydroamination reaction of 1-halo-2-alkynylbenzene with amines afforded the substituted 3-methyleneisoindolin-1-ones in good yields and high selectivities in favor of the Z-isomers. The target molecules could also be synthesized by the Sonogashira coupling-carbonylation-hydroamination one-pot reaction of dihalides, alkynes, and amines. Both processes can be conducted under mild conditions and tolerate a wide array of functionalized substrates.