3-hydroxy-3-(hydroxymethyl)indolin-2-one | 1246745-15-2

• 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: 3-hydroxy-3-(hydroxymethyl)indolin-2-one
• 英文别名: 3-hydroxy-3-hydroxymethyl-oxindole；3-hydroxy-3-(hydroxymethyl)-1H-indol-2-one
• CAS: 1246745-15-2
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: WXCVOKOPENHWHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(tert-butylperoxy)-3-(tert-butylperoxymethyl)-oxindole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以90%的产率得到3-hydroxy-3-(hydroxymethyl)indolin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Tandem Diperoxidation/C−H Activation Resulting in Diperoxy-oxindole in Air

  摘要：

  A highly efficient and facile palladium-catalyzed tandem diperoxidation and C-H activation process was reported, which provides a new pathway for the synthesis of biologically active diperoxides as well as oxindole derivatives from readily available starting materials in excellent chemical yields

  DOI：

  10.1021/ol101664y

文献信息

• Rongalite-induced transition-metal and hydride-free reductive aldol reaction: a rapid access to 3,3′-disubstituted oxindoles and its mechanistic studies
  作者：Sivaparwathi Golla、Naveenkumar Anugu、Swathi Jalagam、Hari Prasad Kokatla

  DOI：10.1039/d1ob02284a

  日期：——

  3′-disubstituted oxindoles from isatin derivatives using rongalite. In this protocol, rongalite plays a dual role as a hydride-free reducing agent and a C1 unit donor. This transition metal-free method enables the synthesis of a wide range of 3-hydroxy-3-hydroxymethyloxindoles and 3-amino-3-hydroxymethyloxindoles with 79–96% yields. One-pot reductive hydroxymethylation, inexpensive rongalite (ca. $0.03/1 g)

  已经开发了一种无过渡金属和无氢化物的还原羟醛反应，用于使用雕白粉从靛红衍生物合成具有生物活性的 3,3'-二取代羟吲哚。在该协议中，雕白粉作为无氢化物还原剂和 C1 单位供体发挥双重作用。这种不含过渡金属的方法能够以 79-96% 的产率合成各种 3-羟基-3-羟甲基羟吲哚和 3-氨基-3-羟甲基羟吲哚。一锅还原羟甲基化、廉价的雕白粉（约0.03 美元/1 g）、温和的反应条件和短的反应时间是这种合成方法的一些关键特征。该协议也适用于克级合成。
• Access to 3,3-disubstituted oxindoles <i>via</i> microwave-assisted Cannizzaro and aldol reactions of formaldehyde with isatins and their imines
  作者：Xuan Huang、Hongling Wang、Qingxiang Cao、Yong Li、Junmin Zhang

  DOI：10.1039/d1ra02150h

  日期：——

  3,3-Disubstituted oxindoles are important structure motifs in natural products and pharmaceutical agents. Here we disclose a simple and direct access to this class of molecules by using readily available formaldehyde and isatins (and their imines) as the substrates. The reaction proceeds with the assistance of microwave heating in the presence of a mild base. Formaldehyde behaves as both a reductant

  3,3-二取代羟吲哚是天然产物和药剂中的重要结构基序。在这里，我们通过使用容易获得的甲醛和靛红（以及它们的亚胺）作为底物，公开了一种简单而直接的获得此类分子的方法。反应在弱碱存在下借助微波加热进行。甲醛既是还原剂（通过Cannizzaro 工艺与靛红）又是亲电子试剂。
• [EN] SIMPLE ORGANIC MOLECULES AS CATALYSTS FOR PRACTICAL AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF AMINES AND ALCOHOLS<br/>[FR] MOLÉCULES ORGANIQUES SIMPLES EN TANT QUE CATALYSEURS POUR LA SYNTHÈSE ÉNANTIOSÉLECTIVE PRATIQUE ET EFFICACE D'AMINES ET D'ALCOOLS
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2013131043A1

  公开（公告）日：2013-09-06

  The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules.

  本发明提供了有机分子及其方法，用于有机硼试剂与双键（如亚胺或羰基）之间的反应，以立体选择性地提供手性产物，包括胺和醇等实体，用于制备具有生物活性的分子。
• SIMPLE ORGANIC MOLECULES AS CATALYSTS FOR PRACTICAL AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF AMINES AND ALCOHOLS
  申请人：Trustees of Boston College

  公开号：US20150057451A1

  公开（公告）日：2015-02-26

  The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules.

  本发明提供了有机分子及其方法，用于有机硼试剂与双键（如亚胺或羰基）之间的反应，以立体选择性地提供手性产物，包括胺和醇等实体，这些实体对于制备生物活性分子非常有用。
• US9328061B2
  申请人：——

  公开号：US9328061B2

  公开（公告）日：2016-05-03