4-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)benzonitrile | 1247442-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)benzonitrile
• 英文别名: 4-(4-Chloro-3,5-dimethylpyrazol-1-yl)benzonitrile
• CAS: 1247442-66-5
• 化学式: C₁₂H₁₀ClN₃
• 分子量: 231.685
• InChiKey: NXPJVNZWINYOPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯-2,4-戊二酮 、 4-氰基苯硼酸 在 偶氮二甲酸二叔丁酯 、 copper(II) acetate monohydrate 、 盐酸 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 反应 1.0h， 以63%的产率得到4-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)benzonitrile
  参考文献：
  名称：

  One-pot copper-catalyzed synthesis of N-functionalized pyrazoles from boronic acids

  摘要：

  A straight-forward route to prepare a diverse set of N-aryl pyrazoles via a one-pot copper-catalyzed boronic acid coupling and cyclization protocol is presented. A variety of aryl and heteroaryl N-functionalized pyrazoles not easily accessible by other means were formed in good yield from readily available boronic acid precursors in an operationally simple procedure. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.077

文献信息

• HBF₄/ACN: A simple and efficient protocol for the synthesis of pyrazoles under ambient reaction conditions
  作者：Roktopol Hazarika、Manashjyoti Konwar、Krishnaiah Damarla、Arvind Kumar、Diganta Sarma

  DOI：10.1080/00397911.2019.1692869

  日期：2020.2.1

  Abstract An efficient and novel protocol for pyrazole synthesis has been developed by using fluoroboric acid as the acid catalyst. Simple and easily available 1,3-diketone and hydrazine derivatives are taken as the substrates for this purpose. The reaction entails mild reaction conditions and produces desired pyrazoles in good to excellent yields. Easy accessibility, easy handling, broad substrate

  摘要 开发了一种以氟硼酸为酸催化剂的高效新型吡唑合成方案。为此目的，采用简单且容易获得的 1,3-二酮和肼衍生物作为底物。该反应需要温和的反应条件并以良好至极好的产率产生所需的吡唑。易于访问、易于处理、广泛的基材范围、避免金属催化剂和经济可行性使该协议有利于大多数先前报道的文献。图形概要
• Transition metal containing ionic liquid-assisted one-pot synthesis of pyrazoles at room temperature
  作者：Manashjyoti Konwar、Hanan M F Elnagdy、Praveen Singh Gehlot、Nageshwar D Khupse、Arvind Kumar、Diganta Sarma

  DOI：10.1007/s12039-019-1659-9

  日期：2019.8

  AbstractThe feasible and one of the green ways to synthesize organic compounds especially pyrazole and its derivatives are systematically presented. The one-pot synthesis of pyrazole was achieved by condensation of various hydrazines and 1,3-diketone derivatives at room temperature using transition metal-based ionic liquids. Herein, the unique combination of Fe(III) with ionic liquid is explored and utilized

  摘要系统地介绍了合成有机化合物特别是吡唑及其衍生物的可行方法和绿色方法之一。吡唑的一锅法合成是通过使用过渡金属基离子液体在室温下将各种肼和1,3-二酮衍生物缩合而实现的。在此，探索了Fe（III）与离子液体的独特组合，并将其用作合成吡唑及其衍生物的有效均相催化剂。如此合成的均相催化剂可重复使用至第四周期（产率分别为90％，88％，84％，78％）。 图形摘要吡唑是在室温下在过渡金属基离子液体存在下合成的。从绿色化学的角度来看，离子液体被认为是绿色溶剂，由于其无毒，无腐蚀和不易燃的特性而受到了广泛的关注，而过渡金属作为抗衡阴离子的一部分使其具有更大的催化活性。 。
• One-pot copper-catalyzed synthesis of N-functionalized pyrazoles from boronic acids
  作者：Ramsay E. Beveridge、Dilinie Fernando、Brian S. Gerstenberger

  DOI：10.1016/j.tetlet.2010.07.077

  日期：2010.9

  A straight-forward route to prepare a diverse set of N-aryl pyrazoles via a one-pot copper-catalyzed boronic acid coupling and cyclization protocol is presented. A variety of aryl and heteroaryl N-functionalized pyrazoles not easily accessible by other means were formed in good yield from readily available boronic acid precursors in an operationally simple procedure. (C) 2010 Elsevier Ltd. All rights reserved.