ethyl 6-bromo-2-oxo-4'H-spiro[indoline-3,5'-isoxazole]-3'-carboxylate | 1280219-32-0

• 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: ethyl 6-bromo-2-oxo-4'H-spiro[indoline-3,5'-isoxazole]-3'-carboxylate
• 英文别名: ethyl 6-bromo-2-oxospiro[1H-indole-3,5'-4H-1,2-oxazole]-3'-carboxylate
• CAS: 1280219-32-0
• 化学式: C₁₃H₁₁BrN₂O₄
• 分子量: 339.145
• InChiKey: DNFPREFSZIMZOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-bromo-2-oxo-4'H-spiro[indoline-3,5'-isoxazole]-3'-carboxylate 在 alane N,N-dimethylethylamine complex 、 水 、 双氧水 、 potassium acetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 7.17h， 生成 Flustraminol B
  参考文献：
  名称：

  Efficient assembly of 3-substituted oxindole-based isoxazolines leading to the synthesis of (±)-flustraminol-B and related natural product building blocks

  摘要：

  An efficient synthesis of oxindole-based isoxazolines has been developed and the resulting spirocyclic intermediates have been elaborated to synthetically versatile 3-hydroxy-3-alkyl oxindole building blocks such as the 3-hydroxy-3-methylenecyano-2-oxindoles (6) and gamma-amino alcohols (12). Utility of this methodology is demonstrated through the synthesis of pyrrolo[2,3-b]indolines including the marine natural product (+/-)-flustraminol-B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.005
• 作为产物：
  描述：

  6-bromo-3-methylidene-1H-indol-2-one 、 氯代肟基乙酸乙酯 在 Amberlyst A₂₁ resin 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以77%的产率得到ethyl 6-bromo-2-oxo-4'H-spiro[indoline-3,5'-isoxazole]-3'-carboxylate
  参考文献：
  名称：

  A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids

  摘要：

  A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.

  DOI：

  10.1021/ol200547m

文献信息

• A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids
  作者：Anand Singh、Gregory P. Roth

  DOI：10.1021/ol200547m

  日期：2011.4.15

  A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.
• Efficient assembly of 3-substituted oxindole-based isoxazolines leading to the synthesis of (±)-flustraminol-B and related natural product building blocks
  作者：Anand Singh、Gregory P. Roth

  DOI：10.1016/j.tetlet.2012.07.005

  日期：2012.9

  An efficient synthesis of oxindole-based isoxazolines has been developed and the resulting spirocyclic intermediates have been elaborated to synthetically versatile 3-hydroxy-3-alkyl oxindole building blocks such as the 3-hydroxy-3-methylenecyano-2-oxindoles (6) and gamma-amino alcohols (12). Utility of this methodology is demonstrated through the synthesis of pyrrolo[2,3-b]indolines including the marine natural product (+/-)-flustraminol-B. (C) 2012 Elsevier Ltd. All rights reserved.