2-苄基-3-(4-甲基苯基)吲唑 | 872681-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苄基-3-(4-甲基苯基)吲唑
• 英文名称: 2-benzyl-3-(p-tolyl)-2H-indazole
• 英文别名: 2-benzyl-3-(4-methylphenyl)-2H-indazole；2-benzyl-3-(4-methylphenyl)indazole
• CAS: 872681-96-4
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: SKTGZYCNZVEAIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  513.5±29.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-吗啉基-1-环己烯 在 palladium on activated charcoal 盐酸 、 sodium ethanolate 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 34.0h， 生成 2-苄基-3-(4-甲基苯基)吲唑
  参考文献：
  名称：

  Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents

  摘要：

  To search for novel compounds with potent anti-angiogenic activity, a series of N-1-(substituted benzyl)-3-(4-methylphenyl)-1H-indazoles (16, 18, 20, 22, 24, 26, 28, 30, 32) and N-2-(substituted benzyl)-3-(4-methylphenyl)-2H-indazoles (17, 19, 21, 23, 25, 27, 29, 31, and 33) were synthesized. The structures of these regioisomers were established by IR, UV, and NMR spectral data. 3-(4-Methylphenyl)-1H-indazole (6) and the N-2-substituted derivatives (17, 19, 21, 23, 25, 29, 31, 33) were evaluated for their anti-angiogenic activity. Most of them showed more prominent activity than ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3). Among these tested compounds, 2-(4-chlorobenzyl)-3-(4-methylphenyl)-2H-indazole (19), 2-(4-methylbenzyl)-3-(4-methylphenyl)-2H-indazole (25), and 2-(4-methoxybenzyl)-3-(4-methylphenyl)-2H-indazole (31) showed significant anti-angiogenic activity and are worthy of further investigation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.032

文献信息

• Metal-free, regioselective, visible light activation of 4CzIPN for the arylation of 2<i>H</i>-indazole derivatives
  作者：Rajendhiran Saritha、Sesuraj Babiola Annes、Subburethinam Ramesh

  DOI：10.1039/d1ra02372a

  日期：——

  Highly regioselective organo photocatalysis of 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) for the arylation of 2H-indazole is demonstrated.

  4CzIPN（1,2,3,5-四(咔唑-9-基)-4,6-二氰基苯）的高区域选择性有机光催化剂用于2H-吲哚的芳基化反应。
• Direct C3-Arylation of 2 <i>H</i> -Indazole Derivatives with Aryl Bromides by using Low Loading of a Phosphine-free Palladium Catalyst
  作者：Fatma Belkessam、Mohand Aidene、Jean-François Soulé、Henri Doucet

  DOI：10.1002/cctc.201601420

  日期：2017.6.22

  The palladium-catalyzed direct arylation of 2 H-indazoles with aryl bromides for the preparation of 3-aryl-2 H-indazoles was found to proceed in high yields when using only 0.5–0.1 mol % Pd(OAc)2 catalyst and KOAc as inexpensive base. A wide variety of electron-deficient and electron-rich aryl bromides and also heteroaryl bromides has been successfully employed. Both electron-withdrawing and electron-donating

  当仅使用0.5–0.1 mol％Pd（OAc）2催化剂和KOAc作为钯时，发现钯催化的2 H-吲唑与芳基溴的直接芳基化反应可 制备3-芳基2  H-吲唑。便宜的基地。已经成功地使用了各种各样的缺电子和富电子的芳基溴化物以及杂芳基溴化物。2 H-吲唑上的吸电子和供电子取代基 也被容许。此外，反应可以在“绿色”溶剂环戊基甲基醚中进行。
• Synthesis of N2 - (substituted arylmethyl) -3- (substituted phenyl) indazoles as novel anti-angiogenic agents
  申请人：Kuo Sheng-Chu

  公开号：US20060106032A1

  公开（公告）日：2006-05-18

  Novel compounds of 2-(substituted arylmethyl)-3-(substituted phenyl)-2H-indazoles and 1-(substituted arylmethyl)-3-(substituted phenyl)-1H-indazoles are synthesized, and useful as anti-angiogenic agents.

  合成了2-(取代芳基甲基)-3-(取代苯基)-2H-吲唑并1-(取代芳基甲基)-3-(取代苯基)-1H-吲唑的新化合物，可作为抗血管生成抑制剂。
• Synthesis of N2-(substituted arylmethyl)-3-(substituted phenyl)indazoles as novel anti-angiogenic agents
  申请人：Yung Shin Pharm. Ind. Co., Ltd.

  公开号：US07514465B2

  公开（公告）日：2009-04-07

  Novel compounds of 2-(substituted arylmethyl)-3-(substituted phenyl)-2H-indazoles and 1-(substituted arylmethyl)-3-(substituted phenyl)-1H-indazoles are synthesized, and useful as anti-angiogenic agents.

  合成了2-(取代芳基甲基)-3-(取代苯基)-2H-吲唑啉和1-(取代芳基甲基)-3-(取代苯基)-1H-吲唑啉的新化合物，并且它们可用作抗血管生成剂。
• Synthesis of substituted 2H-indazole derivatives as anti-angiogenic agents
  申请人：Yung Shin Pharm. Ind. Co., Ltd.

  公开号：EP1659115A1

  公开（公告）日：2006-05-24

  Novel compounds of 2-(substituted arylmethyl)-3-(substituted phenyl)-2H-indazoles and 1-(substituted arylmethyl)-3-(substituted phenyl)-1H-indazoles are synthesized, and useful as anti-angiogenic agents.

  合成了 2-(取代芳基甲基)-3-(取代苯基)-2H-吲唑和 1-(取代芳基甲基)-3-(取代苯基)-1H-吲唑的新型化合物，并将其用作抗血管生成剂。