(S)-3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one | 1037185-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one
• 英文别名: (3S)-3-hydroxy-3-phenacyl-1H-indol-2-one
• CAS: 1037185-06-0
• 化学式: C₁₆H₁₃NO₃
• mdl: MFCD00222126
• 分子量: 267.284
• InChiKey: BIOYMYKQUHGHGY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  苯甲酰乙酸 、 靛红 在 quinidine thiourea B 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以17%的产率得到
  参考文献：
  名称：

  双萘基改性的有机催化剂催化的β-酮酸的对映选择性脱羧醛醇醛加成反应

  摘要：

  已经开发了靛红与手性双官能有机催化剂促进的β-酮酸的催化对映体选择性羧化羟醛缩醛加成反应，从而可以轻松合成具有良好对映选择性（最高97％ee）的相应手性3-羟基-3-苯并恶恶唑衍生物。

  DOI：

  10.1016/j.tetlet.2013.04.132

文献信息

• Synthesis of planar chiral [2.2]paracyclophane-based amino thioureas and their application in asymmetric aldol reactions of ketones with isatins
  作者：Yu Lu、Yudao Ma、Shaobo Yang、Manyuan Ma、Hongju Chu、Chun Song

  DOI：10.1016/j.tetasy.2013.07.023

  日期：2013.9

  were used as bifunctional catalysts for organocatalytic enantioselective aldol reactions between ketones and isatins, affording the desired adducts containing a chiral tertiary alcohol in high yields (up to 92% yield) and with good enantioselectivity (up to 88% ee). This is a successful example of employing planar chiral [2.2]paracyclophane-based amino thioureas in asymmetric aldol reactions.

  已经设计并合成了几种新颖的基于[2.2]对环环烷的氨基硫脲。[2.2]对环烷基氨基硫脲被用作双官能催化剂，用于酮和靛红之间的有机催化对映选择性醛醇缩合反应，以高收率（高达92％的收率）和良好的对映选择性（最高收率）提供了所需的含有手性叔醇的加合物。 88％ee）。这是在不对称醛醇缩合反应中使用基于平面手性[2.2]对环硫基的氨基硫脲的成功实例。
• Enantioselective organocatalytic aldol reaction of unactivated ketones with isatins
  作者：Suresh Allu、Nagaraju Molleti、Ramachandrarao Panem、Vinod K. Singh

  DOI：10.1016/j.tetlet.2011.05.013

  日期：2011.8

  Enantioselective organocatalytic direct aldol reaction of unactivated ketones with various isatin derivatives was developed using cinchonine based urea ligand employing a noncovalent catalysis mechanism. Using this protocol we can access functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields with good to excellent enantioselectivities.

  使用基于非共价催化机理的基于辛可宁的脲配体，开发了未活化的酮与各种靛红衍生物的对映选择性有机催化直接羟醛反应。使用此协议，我们可以以良好或优异的对映选择性高产率获得官能化的3-烷基-3-羟基吲哚-2-酮。
• Enantioselective Construction of 3-Hydroxy Oxindoles via Decarboxylative Addition of β-Ketoacids to Isatins
  作者：Fangrui Zhong、Weijun Yao、Xiaowei Dou、Yixin Lu

  DOI：10.1021/ol301855w

  日期：2012.8.3

  The first highly enantioselective decarboxylative addition of β-ketoacids to isatins mediated by a bifunctional tertiary amine–thiourea catalyst has been developed, allowing facile synthesis of biologically important 3-hydroxy oxindoles in good yields and excellent enantioselectivities. The method reported represents a valuable approach of utilizing β-ketoacids as synthetic equivalents of aryl/alkyl

  已经开发了由双官能叔胺-硫脲催化剂介导的向靛红中β-酮酸的高对映选择性脱羧首次加成反应，可以轻松地以高收率和优异的对映选择性合成重要的生物重要的3-羟基羟吲哚。报告的方法代表了一种利用β-酮酸作为芳基/烷基甲基酮烯醇酸酯的合成等效物的有价值的方法。
• Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins
  作者：Zhiqiang Duan、Jianlin Han、Ping Qian、Zirui Zhang、Yi Wang、Yi Pan

  DOI：10.1039/c3ob41460d

  日期：——

  A ytterbium(III)-indapybox catalysed enantioselective decarboxylative addition reaction of β-ketoacids to isatins is described. The biologically important 3-hydroxy oxindoles were obtained in high yields and excellent enantioselectivities.

  描述了镱(III)-吲哚吡啶催化β-酮酸与异喹啉的对映选择性脱羧加成反应。以高收率和优异的对映选择性获得了具有重要生物学意义的3-羟基吲哚啉。
• Asymmetric aldol reactions of isatins catalyzed by phthalimido-prolinamide
  作者：Togapur Pavan Kumar、Nemali Manjula、Kumar Katragunta

  DOI：10.1016/j.tetasy.2015.09.018

  日期：2015.12

  Enantioselective aldol reactions of isatins with acetone using phthalimido-prolinamide organocatalyst 1 are described. The protocol was effective under solvent free and additive free reaction conditions with 20 mol % of 1 leading to the desired aldol products in good yields and with good enantioselectivities. (C) 2015 Elsevier Ltd. All rights reserved.