2-(5-fluoro-3-hydroxy-2-oxoindolin-3-yl)acetonitrile | 1280219-47-7

• 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: 2-(5-fluoro-3-hydroxy-2-oxoindolin-3-yl)acetonitrile
• 英文别名: 2-(5-fluoro-3-hydroxy-2-oxo-1H-indol-3-yl)acetonitrile
• CAS: 1280219-47-7
• 化学式: C₁₀H₇FN₂O₂
• mdl: MFCD24388935
• 分子量: 206.176
• InChiKey: AJHXZDXYIGOSOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 5-fluoro-2-oxo-4'H-spiro[indoline-3,5'-isoxazole]-3'-carboxylate 在 potassium acetate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以90%的产率得到2-(5-fluoro-3-hydroxy-2-oxoindolin-3-yl)acetonitrile
  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

• Krapcho Dealkoxycarbonylation Strategy of Ethyl Cyanoacetate for the Synthesis of 3-Hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-Dicyanomethyl-2-oxindoles in a Reaction with Isatin
  作者：Keshri Nath Tiwari、Chandran R.

  DOI：10.1055/s-0040-1707816

  日期：2020.8

  A new strategy for the synthesis of 3-hydroxy-3-cyanomethyl-2-oxindoles and 3,3′-dicyanomethyl-2-oxindoles in a reaction of isatin with ethyl cyanoacetate by Krapcho dealkoxycarbonylation reaction in aqueous media is demonstrated. The reaction provides an easy access to synthetically and medicinally valuable oxindole alkylnitriles in good to very good yields. Wider substrate scope and operationally

  提出了一种在水性介质中通过Krapcho脱氧羰基羰基化反应在靛红与氰基乙酸乙酯反应中合成3-羟基-3-氰基甲基-2-氧吲哚和3,3'-二氰基甲基-2-氧吲哚的新策略。该反应提供了易于获得的合成和医学上有价值的羟吲哚烷基腈，收率很高。较宽的基板范围和操作简单的实验程序是已开发协议的突出特点。在控制实验的基础上，合理化了水的反应机理和协同效应。