(3-Hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-acetaldehyde | 700359-38-2

• 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-2-oxo-2,3-dihydro-1H-indol-3-yl)-acetaldehyde
• 英文别名: 2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetaldehyde
• CAS: 700359-38-2
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: HALQJGAURXTRRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-Hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-acetaldehyde 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以13.3 mg的产率得到3-hydroxy-3-(2-hydroxyethyl)indolin-2-one
  参考文献：
  名称：

  N-（杂芳烃磺酰基）脯氨酰胺对（R）-卷旋嘧啶B和E的首次对映选择性合成

  摘要：

  交叉醛醇缩合反应：使用双功能有机催化剂，通过乙醛与4,6-二溴异丁香苷的交叉醇醛缩合反应（1：X = Y = Br）合成了（R）-卷积环糊精E。这种策略允许对映体选择性合成（R）-convolutamydine E衍生物和convolutamydine B.

  DOI：

  10.1002/chem.200900944
• 作为产物：
  描述：

  3-allyl-3-hydroxyindolin-2-one 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 2.17h， 生成 (3-Hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-acetaldehyde
  参考文献：
  名称：

  Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones

  摘要：

  Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (+/-)-donaxaridine, as well as (+/-)-convolutamydines A and E , was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.031

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。
• 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。
• First Enantioselective Synthesis of (<i>R</i>)-Convolutamydine B and E with<i>N</i>-(Heteroarenesulfonyl)prolinamides
  作者：Noriyuki Hara、Shuichi Nakamura、Norio Shibata、Takeshi Toru

  DOI：10.1002/chem.200900944

  日期：2009.7.13

  Crossed‐aldol reaction: The synthesis of (R)‐convolutamydine E has been achieved by the crossed‐aldol reaction of acetaldehyde with 4,6‐dibromoisatin (1: X = Y = Br) by using a bifunctional organocatalyst. This strategy allows the enantioselective synthesis of (R)‐convolutamydine E derivatives and convolutamydine B.

  交叉醛醇缩合反应：使用双功能有机催化剂，通过乙醛与4,6-二溴异丁香苷的交叉醇醛缩合反应（1：X = Y = Br）合成了（R）-卷积环糊精E。这种策略允许对映体选择性合成（R）-convolutamydine E衍生物和convolutamydine B.
• Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones
  作者：Tomomi Kawasaki、Miyuki Nagaoka、Tomoko Satoh、Ayako Okamoto、Rie Ukon、Atsuyo Ogawa

  DOI：10.1016/j.tet.2004.02.031

  日期：2004.4

  Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (+/-)-donaxaridine, as well as (+/-)-convolutamydines A and E , was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. (C) 2004 Elsevier Ltd. All rights reserved.