5-(2-aminophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine | 1195785-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(2-aminophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine
• 英文别名: 2-(3-Methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzenamine；2-(3-methyl-1-phenylpyrazolo[3,4-b]pyridin-5-yl)aniline
• CAS: 1195785-13-7
• 化学式: C₁₉H₁₆N₄
• 分子量: 300.363
• InChiKey: ZFYKIAFJHGVGDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 5-氨基-3-甲基-1-苯基吡唑 在 溶剂黄146 作用下， 反应 4.0h， 以57%的产率得到5-(2-aminophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine
  参考文献：
  名称：

  3-Acylindoles as versatile starting materials for pyridine ring annulation: synthesis of 1-deazapurine isosteres

  摘要：

  The reaction of electron-rich aminoheterocycles with 3-acyl- and 3-formylindoles results in indole ring opening and cyclocondensation to give heteroannulated pyridines, which can be regarded as purine isosteres. The transformations reported herein represent rare examples of domino reactions, which include the cleavage of an indole moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.037

文献信息

• An Efficient One-Step Synthesis of Heterobiaryl Pyrazolo[3,4-<i>b</i>]pyridines via Indole Ring Opening
  作者：Sanghee Lee、Seung Bum Park

  DOI：10.1021/ol902147u

  日期：2009.11.19

  A mild one-step synthetic method to access privileged heterobiaryl pyrazolo[3,4-b]pyridines from indole-3-carboxaldehyde derivatives and a variety of aminopyrazoles has been developed. This novel method constructs heterobiaryls with the wide scope of substrate generality and excellent regioselectivity via indole ring opening.