methyl 2-(3-(benzylthio)-1-methyl-2-oxoindolin-3-yl)acrylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 2-(3-(benzylthio)-1-methyl-2-oxoindolin-3-yl)acrylate
• 英文别名: Methyl 2-(3-benzylsulfanyl-1-methyl-2-oxoindol-3-yl)prop-2-enoate；methyl 2-(3-benzylsulfanyl-1-methyl-2-oxoindol-3-yl)prop-2-enoate
• 化学式: C₂₀H₁₉NO₃S
• 分子量: 353.442
• InChiKey: AFJYSRGLYFHIRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-(benzylthio)-1-methyl-2-oxoindolin-3-yl)acrylate 、 苄胺 以 甲醇 为溶剂， 反应 16.0h， 以82%的产率得到methyl 1-benzyl-4-(benzylthio)-4-(2-(methylamino)phenyl)-5-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Highly regioselective synthesis of 3-alkylthio-2-oxindoles via DABCO-catalyzed allylic α-substitution of Morita–Baylis–Hillman carbonates of isatins with various thiols

  摘要：

  The first Lewis base-catalysed allylic sulfuration of Morita-Baylis-Hillman (MBH) adducts derived from ketones (isatins) has been developed, which affords C3-quaternary oxindole derivatives bearing thio-group at 3-position in good to excellent yield (up to 98% yield) under mild reaction conditions. Significantly, the potential utility of the protocol also has been demonstrated by gram-scale synthesis of 3-alkylthio-2-oxindole (3ae), a low catalyst loading (0.3 mol %) and facile conversion of resulting product (3ad) into functionalized pyrrolidinone (5ad). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.031
• 作为产物：
  描述：

  methyl 2-(3-((tert-butoxycarbonyl)oxy)-1-methyl-2-oxoindolin-3-yl)acrylate 、 苄硫醇 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到methyl 2-(3-(benzylthio)-1-methyl-2-oxoindolin-3-yl)acrylate
  参考文献：
  名称：

  Highly regioselective synthesis of 3-alkylthio-2-oxindoles via DABCO-catalyzed allylic α-substitution of Morita–Baylis–Hillman carbonates of isatins with various thiols

  摘要：

  The first Lewis base-catalysed allylic sulfuration of Morita-Baylis-Hillman (MBH) adducts derived from ketones (isatins) has been developed, which affords C3-quaternary oxindole derivatives bearing thio-group at 3-position in good to excellent yield (up to 98% yield) under mild reaction conditions. Significantly, the potential utility of the protocol also has been demonstrated by gram-scale synthesis of 3-alkylthio-2-oxindole (3ae), a low catalyst loading (0.3 mol %) and facile conversion of resulting product (3ad) into functionalized pyrrolidinone (5ad). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.031

文献信息

• 3-(2-丙烯酸酯)-3-硫代氧化吲哚化合物及其制 备方法
  申请人：贵州大学

  公开号：CN103936649B

  公开（公告）日：2016-05-04

  本发明公开了一种3-(2-丙烯酸酯)-3-硫代氧化吲哚化合物，本发明以不同取代的3-(2-丙烯酸酯)-3-OBoc氧化吲哚和硫醇类化合物，经有机碱直接催化加成消除反应，合成了3-(2-丙烯酸酯)-3-硫代氧化吲哚化合物，该类骨架包含潜在的生物活性含硫基团和丙烯酸酯类基团，可以为生物活性筛选提供化合物源，对药物的筛选和制药行业具有重要的应用价值。本发明操作简单易行，原料合成便宜易得，可以在各种有机溶剂中进行，也具有较好的空气稳定性，适用性广，对于各种取代基都有很好的兼容性。
• Highly regioselective synthesis of 3-alkylthio-2-oxindoles via DABCO-catalyzed allylic α-substitution of Morita–Baylis–Hillman carbonates of isatins with various thiols
  作者：Xiong-Wei Liu、Wen-Yong Han、Xiong-Li Liu、Ying Zhou、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2014.10.031

  日期：2014.12

  The first Lewis base-catalysed allylic sulfuration of Morita-Baylis-Hillman (MBH) adducts derived from ketones (isatins) has been developed, which affords C3-quaternary oxindole derivatives bearing thio-group at 3-position in good to excellent yield (up to 98% yield) under mild reaction conditions. Significantly, the potential utility of the protocol also has been demonstrated by gram-scale synthesis of 3-alkylthio-2-oxindole (3ae), a low catalyst loading (0.3 mol %) and facile conversion of resulting product (3ad) into functionalized pyrrolidinone (5ad). (C) 2014 Elsevier Ltd. All rights reserved.