methyl 2-(3-(benzylthio)-5-bromo-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)-5-bromo-1-methyl-2-oxoindolin-3-yl)acrylate
• 英文别名: Methyl 2-(3-benzylsulfanyl-5-bromo-1-methyl-2-oxoindol-3-yl)prop-2-enoate；methyl 2-(3-benzylsulfanyl-5-bromo-1-methyl-2-oxoindol-3-yl)prop-2-enoate
• 化学式: C₂₀H₁₈BrNO₃S
• 分子量: 432.338
• InChiKey: IBVNLUMPYUVXLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 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

• 作为产物：
  描述：

  methyl 2-(5-bromo-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88%的产率得到methyl 2-(3-(benzylthio)-5-bromo-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

• 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.