3-Hydroxy-3-(2-hydroxy-5-methoxy-phenyl)-1,3-dihydro-indol-2-one | 209847-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-Hydroxy-3-(2-hydroxy-5-methoxy-phenyl)-1,3-dihydro-indol-2-one
• 英文别名: 3-hydroxy-3-(2-hydroxy-5-methoxyphenyl)-1H-indol-2-one
• CAS: 209847-88-1
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: GJVWIMGCMCPRFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  靛红 、 4-甲氧基苯酚 在 乙基溴化镁 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到3-Hydroxy-3-(2-hydroxy-5-methoxy-phenyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Reactivity and regioselectivity of magnesium phenolates towards isatins: One-step synthesis of 3-(2-hydroxyaryl)-3-hydroxyindolones

  摘要：

  A variety of aryloxymagnesium bromides react with isatins under extremely mild conditions to provide 3-(2-hydroxyaryl)-3-hydroxyindolones in good yield. The main features of this protocol consist of exceptionally selective ortho-C-alkylation of the ambident phenolate anion and the lack of diarylated products. Moreover, aryloxymagnesium bromides derived from meta-substituted phenols react with isatins exclusively at the sterically less hindered ortho-position of the phenol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00741-2

文献信息

• Reactivity and regioselectivity of magnesium phenolates towards isatins: One-step synthesis of 3-(2-hydroxyaryl)-3-hydroxyindolones
  作者：Piyasena Hewawasam、Matthew Erway

  DOI：10.1016/s0040-4039(98)00741-2

  日期：1998.6

  A variety of aryloxymagnesium bromides react with isatins under extremely mild conditions to provide 3-(2-hydroxyaryl)-3-hydroxyindolones in good yield. The main features of this protocol consist of exceptionally selective ortho-C-alkylation of the ambident phenolate anion and the lack of diarylated products. Moreover, aryloxymagnesium bromides derived from meta-substituted phenols react with isatins exclusively at the sterically less hindered ortho-position of the phenol. (C) 1998 Elsevier Science Ltd. All rights reserved.