1-苯基-1H-吲哚-3-羧酸 | 244090-34-4

• 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
• 中文名称: 1-苯基-1H-吲哚-3-羧酸
• 英文名称: 1-phenyl-1H-indole-3-carboxylic acid
• 英文别名: 1-phenylindole-3-carboxylic acid
• CAS: 244090-34-4
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: XQLRMJHBYLGPDA-UHFFFAOYSA-N

物化性质

• 沸点：
  362.9±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苯基-1H-吲哚-3-羧酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[7-(hydroxyamino)-7-oxoheptyl]-1-phenylindole-3-carboxamide
  参考文献：
  名称：

  Indole amide hydroxamic acids as potent inhibitors of histone deacetylases

  摘要：

  A series of hydroxamic acid-based HDAC inhibitors with an indole amide residue at the terminus have been synthesized and evaluated. Compounds with a 2-indole amide moiety have been found as the most active inhibitors among the different regioisomers. Introduction of substituents on the indole ring further improved the potency and generated a series of very potent inhibitors with significant antiproliferative activity. A representative compound in the series, 7b, has been found to be orally active in tumor growth inhibition model. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00301-9
• 作为产物：
  描述：

  1-苯基-1H-吲哚-3-甲酸甲酯 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-苯基-1H-吲哚-3-羧酸
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9

文献信息

• Rhodium(III)-Catalyzed Oxidative Coupling of <i>N</i>-Phenylindole-3-carboxylic Acids with Alkenes and Alkynes via C4–H and C2–H/C2′–H Bond Cleavage
  作者：Takeshi Okada、Asumi Sakai、Tomoaki Hinoue、Tetsuya Satoh、Yoshihiro Hayashi、Susumu Kawauchi、Kona Chandrababunaidu、Masahiro Miura

  DOI：10.1021/acs.joc.8b00638

  日期：2018.5.18

  The rhodium(III)-catalyzed direct alkenylation of N-phenylindole-3-carboxylic acids with alkenes including acrylate ester, acrylamide, and acrylonitrile proceeds smoothly at the C4-position through regioselective C–H bond cleavage directed by the carboxyl group. In marked contrast, the indole substrates react with diarylacetylenes accompanied by cleavage of the C2–H and C2′–H bonds and decarboxylation

  铑（III）催化的N-苯基吲哚-3-羧酸与包括丙烯酸酯，丙烯酰胺和丙烯腈在内的烯烃进行直接烯基化反应，通过羧基定向的区域选择性C–H键断裂，在C4位置顺利进行。与之形成鲜明对比的是，吲哚底物与二芳基乙炔反应，同时裂解C2-H和C2'-H键并脱羧生成5,6-二芳基吲哚[1,2- a]喹诺酮衍生物。DFT计算表明，将烯烃顺利插入到C4族基的六元金属环中间体中会导致C4烯基化的产物，而后者在C2-和C2'-位上的环化可归因于相应位置的轻松还原消除由双CH键断裂和炔烃插入形成的七元金属环。
• Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes
  作者：Mana Yamashita、Hakaru Horiguchi、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo9016698

  日期：2009.10.2

  palladium-catalyzed oxidative coupling reactions of N-substituted indoles or their carboxylic acid derivatives with alkynes. Unsymmetrically octasubstituted carbazoles can also be obtained by the stepwise couplings of 1-methylpyrrole-2-carboxylic acid with two different alkynes. In addition, the present coupling procedure is applicable to the synthesis of other various heteroarenes possessing di-, tri-, and tetracyclic

  1,2,3,4-四取代咔唑的选择性合成可以通过钯取代的N-取代的吲哚或其羧酸衍生物与炔烃的氧化偶联反应来有效地进行。不对称的八取代咔唑也可以通过1-甲基吡咯-2-羧酸与两种不同炔烃的逐步偶联获得。另外，本偶联方法适用于具有二，三和四环核的其他各种杂芳烃的合成。一些产品在固态下表现出强烈的荧光。
• Regioselective C−H Functionalization Directed by a Removable Carboxyl Group:  Palladium-Catalyzed Vinylation at the Unusual Position of Indole and Related Heteroaromatic Rings
  作者：Atsushi Maehara、Hayato Tsurugi、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol8000602

  日期：2008.3.1

  The palladium-catalyzed oxidative vinylation of indole-3-carboxylic acids with alkenes effectively proceeds via directed C-H functionalization and decarboxylation to produce the corresponding 2-vinylated indoles. Similarly, pyrrole-, furan-, and thiophenecarboxylic acids also undergo decarboxylative vinylation.

  钯催化的吲哚-3-羧酸与烯烃的氧化乙烯基化反应可通过定向CH官能化和脱羧反应有效地进行，以生成相应的2-乙烯基化的吲哚。类似地，吡咯，呋喃和噻吩羧酸也经历脱羧乙烯基化。
• Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling of Heteroarene Carboxylic Acids with Alkynes
  作者：Mana Yamashita、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol900736s

  日期：2009.6.4

  The palladium-catalyzed oxidative coupling of indole-3-carboxylic acids with alkynes effectively proceeds in a 1:2 manner accompanied by decarboxylation to produce the corresponding 1,2,3,4-tetrasubstituted carbazoles, some of which exhibit solid-state fluorescence. Pyrrole-, benzofuran-, and furancarboxylic acids also undergo the decarboxylative coupling to afford highly substituted indole, dibenzofuran

  吲哚-3-羧酸与炔烃的钯催化氧化偶联有效地以1：2方式进行，并伴随脱羧反应生成相应的1,2,3,4-四取代咔唑，其中一些表现出固态荧光。吡咯-，苯并呋喃-和呋喃羧酸也经过脱羧偶合，分别得到高度取代的吲哚，二苯并呋喃和苯并呋喃衍生物。
• 5-HT3 RECEPTOR ANTAGONISTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20160185801A1

  公开（公告）日：2016-06-30

  The present invention provides compounds of the formula: that are 5HT3 receptor antagonists and are therefore useful for the treatment of diseases treatable by inhibition of 5HT3 receptor such as emesis, pain, drug addiction, neurodegenerative and psychiatric disorders, and GI disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供的化合物具有以下公式： 这些化合物是5HT3受体拮抗剂，因此可用于治疗可通过抑制5HT3受体治疗的疾病，例如呕吐、疼痛、药物成瘾、神经退行性和精神障碍以及胃肠道疾病。还提供了包含这些化合物的制药组合物和制备这些化合物的方法。