(R)-3-hydroxy-3-(2-hydroxyethyl)indolin-2-one | 1185745-44-1

• 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: (R)-3-hydroxy-3-(2-hydroxyethyl)indolin-2-one
• 英文别名: 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one；(3R)-3-hydroxy-3-(2-hydroxyethyl)-1H-indol-2-one
• CAS: 1185745-44-1
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: ONTSLQKRQUPLSL-SNVBAGLBSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  462.2±45.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-3-(2-hydroxyethyl)indolin-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到(+/-)-2,3,8,8a-tetrahydro-furo[2,3-b]indol-3a-ol
  参考文献：
  名称：

  Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of ent-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B

  摘要：

  The asymmetric aldol reaction of isatin derivatives and acetaldehyde has been developed using 4-hydroxydiarylprolinol as a catalyst, affording the aldol products with high enantioselectivity, these products being key intermediates in the synthesis of 3-hydroxyindole alkaloids. Short syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B have been accomplished.

  DOI：

  10.1021/ol901432a
• 作为产物：
  描述：

  2-[(3R)-3-hydroxy-2-oxo-1H-indol-3-yl]acetaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-3-hydroxy-3-(2-hydroxyethyl)indolin-2-one
  参考文献：
  名称：

  未活化酮与靛红的对映选择性有机催化醛醇缩合反应

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2011.05.013

文献信息

• Chiral Primary Amine Catalyzed Asymmetric Direct Cross-Aldol Reaction of Acetaldehyde
  作者：Shenshen Hu、Long Zhang、Jiuyuan Li、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.201100267

  日期：2011.6

  The first primary aminocatalytic direct cross-aldol reaction of acetaldehyde is presented. Among the various vicinal diamines screened, the L-tert-leucine derivative 1c in conjunction with (H4SiW12O40)0.25 was identified as the optimal catalyst; good catalytic activity (up to 99 % yield in 4 h), and high enantioselectivities (up to 92 % ee) were achieved for a range of donors, including aromatic aldehydes

  介绍了乙醛的第一个伯氨基催化直接交叉羟醛反应。在筛选的各种邻二胺中，L-叔亮氨酸衍生物1c与(H4SiW12O40)0.25结合被确定为最佳催化剂；对一系列供体（包括芳香醛和靛红衍生物）实现了良好的催化活性（4 小时内高达 99% 的产率）和高对映选择性（高达 92% ee）。乙醛水溶液和三聚乙醛可以方便地应用于该系统。
• Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxyindolin-2-ones
  作者：Qunsheng Guo、Mayur Bhanushali、Cong-Gui Zhao

  DOI：10.1002/anie.201004161

  日期：2010.12.3

  New catalysis mechanism! The asymmetric aldol reaction of unactivated ketones and activated carbonyl compounds is realized with a quinidine‐derived thiourea catalyst (see scheme), and involves an enolate mechanism instead of the widely used enamine mechanism. With isatins as the substrate, the reaction can be applied to the enantioselective synthesis of biologically active 3‐hydroxyindolin‐2‐ones.

  新的催化机制！未活化的酮和活化的羰基化合物的不对称醛醇反应是通过奎尼丁衍生的硫脲催化剂实现的（见方案），并且涉及烯醇机制而不是广泛使用的烯胺机制。以靛红为底物，该反应可用于对映选择性合成具有生物活性的 3-羟基吲哚-2-酮。
• Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (−)-donaxaridine and (R)-chimonamidine
  作者：Wen-Bing Chen、Xi-Lin Du、Lin-Feng Cun、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2009.12.041

  日期：2010.2

  A highly enantioselective aldol reaction of acetaldehyde and a wide scope of isatins has been presented only using readily available 4-hydroxydiarylprolinol as catalyst, affording various desired 3-substituted 3-hydroxyindolin-2-one adducts with moderate to high yield (up to 95%) and good enantioselectivities (up to 98% ee). This method not only represents an example of concise stereoselective synthesis

  仅使用容易获得的4-羟基二芳基脯氨醇作为催化剂，才呈现出乙醛和多种isatin的高度对映选择性醛醇缩合反应，可提供中等至高收率（高达95％）的各种所需的3-取代的3-hydroxy 3-indolin-2-one加合物）和良好的对映选择性（最高98％ee）。该方法不仅代表了对映纯（R）-卷积嘧啶B和E的简洁的立体选择性合成的例子，而且首先展示了具有光学活性的（-）-多纳沙丁啶和（R）-烟酰胺的不对称合成。
• 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。
• A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins - A Concise Total Synthesis of Antitumor Agents
  作者：Ummareddy Venkata Subba Reddy、Madhu Chennapuram、Kento Seki、Chigusa Seki、Bheemreddy Anusha、Eunsang Kwon、Yuko Okuyama、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1002/ejoc.201700399

  日期：2017.7.17

  metal-free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC-1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible

  已使用一系列简单的二氨基醇催化剂开发了靛红衍生物和乙醛的对映选择性交叉羟醛缩合反应，以高化学收率（高达95％）和光学纯度（高达92％）提供了3-取代的3-羟基吲哚-2-酮。  ee）。本方案的合成潜力已通过具有锥虫素结构的抗肿瘤药和抗病毒药的简明，对映体选择性，无保护基团和无过渡金属的总合成得到了证明，这就是类泛素B和脑啡肽A以及具有生物活性的吲哚啶生物碱，mon胺和多那西啶以及CPC-1的正式合成。通过计算可能的过渡态的吉布斯自由能，评估了该催化的交叉羟醛反应的高度对映选择性。