(S)-(2-oxocyclohexyl)-3-hydroxyindolin-2-one | 1312942-26-9

• 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: (S)-(2-oxocyclohexyl)-3-hydroxyindolin-2-one
• 英文别名: (3S)-3-hydroxy-3-(2-oxocyclohexyl)-1H-indol-2-one
• CAS: 1312942-26-9
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: VWHKAOILSLADJS-LNUXAPHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 、 环己酮 在 C₁₄H₂₂N₂O*2ClH 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以90%的产率得到(S)-(2-oxocyclohexyl)-3-hydroxyindolin-2-one
  参考文献：
  名称：

  Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine

  摘要：

  The enantioselective organocatalytic direct aldol reactions of ketones with various aldehydes were developed by using chiral 1,2-cyclohexanediamine COACH) based multifunctional ligands via a noncovalent catalysis mechanism. By using a catalyst, we also obtained functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields and with good to excellent enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.017

文献信息

• Carbohydrate-derived alcohols as organocatalysts in enantioselective aldol reactions of isatins with ketones
  作者：Chao Shen、Fangyi Shen、Haijun Xia、Pengfei Zhang、Xinzhi Chen

  DOI：10.1016/j.tetasy.2011.04.007

  日期：2011.3

  The catalytic activity of carbohydrate-derived amino alcohols in the enantioselective aldol reaction of ketones with isatin and its derivatives has been examined for the first time. The carbohydrate-derived amino alcohols 5 were found to be efficient organocatalysts for asymmetric aldol reactions. A variety of isatins were used as substrates and the corresponding aldol products were obtained in high yields (up to 99%) and with moderate enantioselectivities (up to 75%). Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine
  作者：Lei Li、Shaohua Gou、Fei Liu

  DOI：10.1016/j.tetasy.2013.11.017

  日期：2014.1

  The enantioselective organocatalytic direct aldol reactions of ketones with various aldehydes were developed by using chiral 1,2-cyclohexanediamine COACH) based multifunctional ligands via a noncovalent catalysis mechanism. By using a catalyst, we also obtained functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields and with good to excellent enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.