diethyl 2-[2-(N-benzylanilino)-2-oxoethylidene]propanedioate | 880256-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 2-[2-(N-benzylanilino)-2-oxoethylidene]propanedioate
• CAS: 880256-14-4
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: SDPKUIZKCXTLJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-[2-(N-benzylanilino)-2-oxoethylidene]propanedioate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到diethyl 2-(1-benzyl-2-oxo-3H-indol-3-yl)propanedioate
  参考文献：
  名称：

  A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives

  摘要：

  Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.

  DOI：

  10.3987/com-05-s(t)25
• 作为产物：
  描述：

  1,1-diethyl 2-hydrogen ethenetricarboxylate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 diethyl 2-[2-(N-benzylanilino)-2-oxoethylidene]propanedioate
  参考文献：
  名称：

  A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives

  摘要：

  Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.

  DOI：

  10.3987/com-05-s(t)25

文献信息

• A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives
  作者：Shoko Yamazaki、Machiko Yamamoto、Satoshi Morikawa

  DOI：10.3987/com-05-s(t)25

  日期：——

  Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.