4-(benzyloxy)-1H-indole-3-carboxylic acid | 24370-72-7

• 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: 4-(benzyloxy)-1H-indole-3-carboxylic acid
• 英文别名: 4-(benzyloxy)-1H-indole-3-carboxylate；4-benzyloxy-indole-3-carboxylic acid；4-Benzyloxy-indol-carbonsaeure-(3)；4-Benzyloxy-indol-3-carbonsaeure；4-phenylmethoxy-1H-indole-3-carboxylic acid
• CAS: 24370-72-7
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: VJKXHBLVYPBZDX-UHFFFAOYSA-N

物化性质

• 沸点：
  531.1±35.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-1H-indole-3-carboxylic acid 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 N-(4-t-butylphenyl)-4-(pyridin-4-ylmethoxy)-1H-indole-3-carboxamide
  参考文献：
  名称：

  KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.01.063
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4-(benzyloxy)-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.01.063

文献信息

• Base-Mediated Carboxylation of Unprotected Indole Derivatives with Carbon Dioxide
  作者：Woo-Jin Yoo、Montse Guiteras Capdevila、Xiangwei Du、Shu̅ Kobayashi

  DOI：10.1021/ol3025082

  日期：2012.10.19

  A simple and straightforward method for the preparation of indole-3-carboxylic acids was discovered through the direct carboxylation of indoles with atmospheric pressure of carbon dioxide (CO2) under basic conditions. The key for the reaction was found to be the use of a large excess of LiO'Bu as a base to suppress the undesired decarboxylation side reaction.
• Lithium tert-Butoxide-Mediated Carboxylation Reactions of Unprotected Indoles and Pyrroles with Carbon Dioxide
  作者：Shū Kobayashi、Woo-Jin Yoo、Thanh V. Q. Nguyen、Montse Guiteras Capdevila

  DOI：10.3987/com-14-s(k)94

  日期：——

  Unprotected indoles and pyrroles were found to undergo base-mediated carboxylation reactions under ambient pressure of carbon dioxide. It was found that this transition metal-free carboxylation reaction proceeded smoothly with the use of a large excess of (LiOBu)-Bu-t.
• US5723462A
  申请人：——

  公开号：US5723462A

  公开（公告）日：1998-03-03
• US5750702A
  申请人：——

  公开号：US5750702A

  公开（公告）日：1998-05-12
• US5925770A
  申请人：——

  公开号：US5925770A

  公开（公告）日：1999-07-20