2-(1H-indol-2-yl)-2-oxoacetic acid | 33588-57-7

• 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: 2-(1H-indol-2-yl)-2-oxoacetic acid
• 英文别名: indol-2-yl-oxo-acetic acid；indol-2-yl-glyoxylic acid；Indol-2-yl-glyoxylsaeure；indolylglyoxylic acid；α-Indolylglyoxylic acid；α-Indolylglyoxylsaeure；Indoleglyoxylic acid
• CAS: 33588-57-7
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: WNZLDRIGCVYTOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  413.0±27.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-indol-2-yl)-2-oxoacetic acid 在 palladium on activated charcoal 氢氧化钾 、 氢溴酸 、 氢气 、 sodium methylate 、 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  玫瑰树碱的合成

  摘要：

  6H-吡啶并[4,3-b]咔唑系统是通过酯烯酸酯对未活化吡啶鎓盐的分子内攻击而有效合成的。

  DOI：

  10.1016/s0040-4039(01)81172-2
• 作为产物：
  描述：

  N-苯磺酸吲哚 在 正丁基锂 、 水 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 8.0h， 生成 2-(1H-indol-2-yl)-2-oxoacetic acid
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032

文献信息

• A Facile Pathway to Enantiomerically Enriched 3-Hydroxy-2-Oxindoles: Asymmetric Intramolecular Arylation of α-Keto Amides Catalyzed by a Palladium-DifluorPhos Complex
  作者：Liang Yin、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1002/anie.201102158

  日期：2011.8.8

  Less metal wastes: The first catalytic, enantioselective intramolecular aryl‐transfer reaction of aryl triflates to ketones has been developed (see scheme; R1=R2=aromatic and aliphatic). This method features overall practicality, including substrate stability and accessibility (protecting‐group free) plus no need for the use of stoichiometric amounts of metals.

  减少金属废料：已开发出芳基三氟甲磺酸酯向酮的第一个催化，对映选择性分子内芳​​基转移反应（参见方案； R 1 = R 2 =芳族和脂族）。该方法具有整体实用性，包括基材稳定性和可及性（无保护基团），而且无需使用化学计量的金属。
• Generation and Intermolecular Reactions of 2-Indolylacyl Radicals
  作者：M.-Lluïsa Bennasar、Tomàs Roca、Rosa Griera、Joan Bosch

  DOI：10.1021/ol0100576

  日期：2001.5.1

  corresponding phenyl selenoesters, aldehydes, and alpha-keto carboxylic acids and the scope of their participation in intermolecular addition reactions to carbon-carbon double bonds have been studied. Whereas the phenyl selenoester method has provided easy access to a variety of 1,4-dicarbonyl compounds bearing the 2-acylindole moiety, the glyoxylic acid route has been employed for the preparation of 2-indolyl

  已经研究了由相应的苯基硒酸酯，醛和α-酮基羧酸生成2-吲哚基的自由基，以及它们参与分子间加成反应的范围。尽管苯基硒酸酯方法使人们容易接近带有2-酰基环部分的各种1，4-二羰基化合物，但乙醛酸途径已用于制备2-吲哚基吡啶基酮。
• Improvements in or relating to indolylglycyl cephalosporin derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0122157A2

  公开（公告）日：1984-10-17

  7-(3-Indolyl)glycylamido cephalaosporins provided by this invention possess favorable pharmocokinetics and are orally effective against gram positive microorganisms.

  本发明提供的 7-(3-吲哚基)甘氨酰氨基头孢菌素具有良好的药代动力学，对革兰氏阳性微生物口服有效。
• Synthesis and reactions of N-protected 2-lithiated pyrroles and indoles. The tert-butoxycarbonyl substituent as a protecting group
  作者：Iltifat Hasan、Edmund R. Marinelli、Li-Ching Chang Lin、Frank W. Fowler、Alan B. Levy

  DOI：10.1021/jo00314a034

  日期：1981.1
• (<i>Z</i>)-Stereoselective Synthesis of<i>Mono</i>- and<i>Bis</i>-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction
  作者：Zhigang Xu、Guillermo Martinez-Ariza、Alexandra P. Cappelli、Sue A. Roberts、Christopher Hulme

  DOI：10.1021/acs.joc.5b00955

  日期：2015.9.18

  Several novel cascade reactions are herein reported that enable access to a variety of unique mono- and bis-heterocyclic scaffolds. The sequence of cascade events are mediated through acid treatment of an Ugi adduct that affords 1,5-benzodiazepines which subsequently undergo an elegant rearrangement to deliver (E)-benzimidazolones, which through acid-promoted tautomerization convert to their corresponding (Z)-isomers. Moreover, a variety of heterocycles tethered to (Z)-benzimidazole-2-ones are also accessible through similar domino-like processes, demonstrating a general strategy to access significantly new scaffold diversity, each containing four points of potential diversification. Final structures of five scaffolds have been definitively proven by X-ray crystallography.