3-(4-methylphenyl)-4,5,6,7-tetrahydro-1H-indazole | 872681-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-methylphenyl)-4,5,6,7-tetrahydro-1H-indazole
• 英文别名: 3-(p-tolyl)-4,5,6,7-tetrahydro-1H-indazole
• CAS: 872681-95-3
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: GCYLOQNOLAGIJF-UHFFFAOYSA-N

物化性质

• 熔点：
  57-60 °C
• 沸点：
  436.5±34.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)-4,5,6,7-tetrahydro-1H-indazole 在 钯 Petroleum ether 作用下， 以 trans-decalin 为溶剂， 反应 4.0h， 以to afford 3-(4-methylphenyl)-1H-indazole (10, 9.85 g, 82% yield)的产率得到3-(4-甲基苯基)-1H-吲唑
  参考文献：
  名称：

  Synthesis of N2-(substituted arylmethyl)-3-(substituted phenyl)indazoles as novel anti-angiogenic agents

  摘要：

  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。

  公开号：

  US07514465B2
• 作为产物：
  描述：

  1-吗啉基-1-环己烯 在 盐酸 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 8.5h， 生成 3-(4-methylphenyl)-4,5,6,7-tetrahydro-1H-indazole
  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

• An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride
  作者：Vit Lellek、Cheng-yi Chen、Wanggui Yang、Jie Liu、Xuebao Ji、Roger Faessler

  DOI：10.1055/s-0036-1591941

  日期：2018.5

  hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or

  开发了一种高效、单锅且无金属的制备多克规模的 3,5-二取代和 3,4,5-三取代吡唑的方法。在温和条件下，酮、醛和肼单盐酸盐的一锅缩合容易形成吡唑啉中间体。使用溴原位氧化吡唑啉得到多种吡唑。该方法为合成 3,4,5-取代吡唑的 3,4,5-取代吡唑类化合物提供了一种快速且通常无需色谱的方案，收率非常好。或者，通过简单地在 DMSO 中在氧气下加热吡唑啉，更温和的氧化方案提供 3,5-二取代或 3,4,5-三取代的吡唑。
• 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 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。
• US7514465B2
  申请人：——

  公开号：US7514465B2

  公开（公告）日：2009-04-07