1H-indol-3-ol anion

• 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: 1H-indol-3-ol anion
• 英文别名: 1H-indol-3-olate
• 化学式: C₈H₆NO
• 分子量: 132.142
• InChiKey: PCKPVGOLPKLUHR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonate 、 1H-indol-3-ol anion 在 N,N'-bis(6A-deoxy-β-cyclodextrin-6A-yl)NHCOCONH 作用下， 以 水 为溶剂， 以36%的产率得到indirubin-5'-sulfonate
  参考文献：
  名称：

  A cyclodextrin-based molecular reactor to template the formation of indigoid dyes

  摘要：

  N,N'-Bis(6(A)-deoxy-beta-cyclodextrin-6(A)-yl)urea behaves as a molecular reactor to bias competing reactions of indoxyl anion and isatin-5-sulfonate in water, to give indigo and indirubin-5'-sulfonate. It appears that the cyclodextrin dimer increases the relative reactivity of the isatin-5-sulfonate, by selectively complexing the reactive form. The molecular host also aligns the isatinsulfonate with indoxyl anion to favour production of indirubin-5'-sulfonate, with the result that the ratio of indigo and indirubin-5'-sulfonate produced is altered by a factor of at least 3500, without a substantial loss of yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01403-5

文献信息

• A cyclodextrin-based molecular reactor to template the formation of indigoid dyes
  作者：Jason B Harper、Christopher J Easton、Stephen F Lincoln

  DOI：10.1016/s0040-4039(03)01403-5

  日期：2003.7

  N,N'-Bis(6(A)-deoxy-beta-cyclodextrin-6(A)-yl)urea behaves as a molecular reactor to bias competing reactions of indoxyl anion and isatin-5-sulfonate in water, to give indigo and indirubin-5'-sulfonate. It appears that the cyclodextrin dimer increases the relative reactivity of the isatin-5-sulfonate, by selectively complexing the reactive form. The molecular host also aligns the isatinsulfonate with indoxyl anion to favour production of indirubin-5'-sulfonate, with the result that the ratio of indigo and indirubin-5'-sulfonate produced is altered by a factor of at least 3500, without a substantial loss of yield. (C) 2003 Elsevier Ltd. All rights reserved.