4-碘-3-吲哚羧酸甲酯 | 101909-44-8

• 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: 4-碘-3-吲哚羧酸甲酯
• 英文名称: 4-iodo-1H-indolo-3-carboxylic acid methyl ester
• 英文别名: 4-iodo-indole-3-carboxylic acid methyl ester；methyl 4-iodo-1H-indole-3-carboxylate；methyl 4-iodo-3-indolecarboxylate；4-iodo-3-methoxycarbonylindole
• CAS: 101909-44-8
• 化学式: C₁₀H₈INO₂
• 分子量: 301.084
• InChiKey: RLXRPTKPAIJVLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-碘-3-吲哚羧酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 49.5h， 生成 3-二甲基氨基甲基-4-碘吲哚
  参考文献：
  名称：

  The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position.

  摘要：

  首次合成了多种4-卤代-3-吲哚乙酸和-3-吲哚乙腈，采用了桑德梅耶反应或施密特反应，展示了4-吲哚二氮盐在4-取代吲哚化学中的多样性。通过区域选择性的铊化-卤化开发了一种实用的4-卤代吲哚合成方法，所生成的产品也可转化为4-卤代-3-吲哚乙酸。此外，还报道了4-甲酰基-3-吲哚乙腈的首次合成。

  DOI：

  10.1248/cpb.33.3696
• 作为产物：
  描述：

  4-碘吲哚-3-甲醛 在 sodium chlorite 、 2-甲基-丁烯 作用下， 以 乙醚 为溶剂， 生成 4-碘-3-吲哚羧酸甲酯
  参考文献：
  名称：

  Yamada, Fumio; Somei, Masanori, Heterocycles, 1987, vol. 26, # 5, p. 1173 - 1176

  摘要：

  DOI：

文献信息

• A New Synthesis of Lysergic Acid
  作者：James B. Hendrickson、Jian Wang

  DOI：10.1021/ol0354369

  日期：2004.1.1

  [reaction: see text] (+/-)-Lysergic acid has been synthesized via an economical 8-step route from 4-bromoindole and isocinchomeronic acid without the need to protect the indole during the synthesis. Initial efforts to form the simpler 3-acylindole derivatives first and then cyclize these were unsuccessful in the cyclization step.

  [反应：见正文]（+/-）-麦角酸是通过经济的8步路线由4-溴吲哚和异辛烯酸合成的，不需要在合成过程中保护吲哚。首先在环化步骤中未能成功形成较简单的3-acylindole衍生物，然后将其环化的初步努力。
• Enantioselective Synthesis of (−)-<i>cis</i>-Clavicipitic Acid
  作者：Jin-Mo Ku、Byeong-Seon Jeong、Sang-sup Jew、Hyeung-geun Park

  DOI：10.1021/jo071162h

  日期：2007.10.1

  An enantioselective synthetic method for (−)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer catalytic alkylation and diastereoselective Pd(II)-catalyzed intramolecular aminocyclization as key steps.

  报道了对-（-）-顺式-克拉维酸（1）的对映选择性合成方法。1在10步（99％ee的和20％的总收率），从1中得到ħ -吲哚-3-羧酸甲酯（9经由不对称相转移催化的烷基化和非对映选择性钯（II）催化的分子内aminocyclization作为密钥）脚步。
• KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives
  作者：Takahiro Honda、Hironori Nagahara、Hiroyuki Mogi、Masakazu Ban、Hiroyuki Aono

  DOI：10.1016/j.bmcl.2011.01.063

  日期：2011.3

  We previously reported that compound 1, having a similar conformation to PTK787 (2) by forming a pseudo ring structure with an intramolecular non-bonded S-O interaction, exhibited a potent inhibitory activity against VEGFR2 tyrosine kinase (KDR).(1) Applying the ideas of pseudo ring formations, we have designed three types of novel indole carboxamide derivatives 5-7 with an intramolecular hydrogen bonding or non-bonded S-O interaction. We describe the design and synthesis of 5-7, and also discuss the relationships of their KDR inhibitory activity and conformations that were stabilized by their intramolecular non-bonded interactions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• 3-Indolylacyl Radical Cyclizations upon Pyridines and Tetrahydropyridines: Access to Ergoline-Related Indole [<i>cd</i>]-fused Isoquinolines
  作者：M.-Lluïsa Bennasar、Tomàs Roca

  DOI：10.1021/jo2006279

  日期：2011.5.20

  Cyclizations of selenoester-derived 3-indolylacyl radicals, involving the homolytic acylation of pyridines or the addition to double bonds included in tetrahydropyridine rings, have been used to synthesize indole [cd]-fused isoquinolines related to the natural ergoline system.
• Ohta, Toshiharu; Yamato, Yoshinori; Tahira, Hiroko, Heterocycles, 1987, vol. 26, # 11, p. 2817 - 2822
  作者：Ohta, Toshiharu、Yamato, Yoshinori、Tahira, Hiroko、Somei, Masanori

  DOI：——

  日期：——