1-(4-bromophenyl)-4-chloro-1H-pyrazole | 1248589-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-4-chloro-1H-pyrazole
• 英文别名: 1-(4-Bromophenyl)-4-chloropyrazole
• CAS: 1248589-16-3
• 化学式: C₉H₆BrClN₂
• 分子量: 257.517
• InChiKey: PCAFGKZXRRGMKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(4-溴苯基)-1H-吡唑 在 三氯异氰尿酸 、 silica gel 作用下， 以 neat (no solvent) 为溶剂， 以99 %的产率得到1-(4-bromophenyl)-4-chloro-1H-pyrazole
  参考文献：
  名称：

  三氯异氰尿酸无溶剂机械化学氯化吡唑

  摘要：

  描述了一种无溶剂、快速且操作简单的方法，用于用三氯异氰尿酸氯化吡唑以获得 4-氯吡唑衍生物。这种高产方案避免了繁琐的柱层析并减少了溶剂消耗。机理研究表明亲电子芳族取代机制。该系统还提供了良好的绿色化学指标。

  DOI：

  10.1039/d3gc00170a

文献信息

• [EN] PYRAZOLOPYRIMIDINES AS ANTI - HEPATITS C AGENTS<br/>[FR] PYRAZOLOPYRIMIDINES UTILISES COMME AGENTS ANTI-HEPATITE C
  申请人：ARROW THERAPEUTICS LTD

  公开号：WO2005047288A1

  公开（公告）日：2005-05-26

  Pyrazolopyrimidine derivatives of formula (I), or a pharmaceutically acceptable salt thereof, are found to be active against hepatitis C infection, wherein: R1 is C6-C10 aryl, 5- to 10- membered heteroary1, -(C1-C4 alkyl)-(C6-C10 aryl) or -(C1-C4 alkyl)-(5- to 10- membered heteroaryl); R2 is a C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10- membered heterocyclyl moiety, said moiety being optionally fused to a C6­C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heteroaryl or 5- to 10­membered heterocyclic ring; and X is -NR'-, -NR'-CO-NR''-, -NR'-L, or -NR'-CO-L-, wherein R' and R'' are the same or different and each represent hydrogen or a C1-C6 alkyl group and L represents a C1-C6 alkylene group, the aryl, heteroaryl, heterocyclyl. and carbocyclyl moieties in the R1 and R2 substituents being unsubstituted or substituted by 1, 2 or 3 substituents selected from halogen, C1-C4 alkyl C1-C4alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, nitro, C6-C10 aryl, C3-C6 carbocyclyl, 5- to 10- membered heterocyclyl, 5- to 10- membered heteroaryl, -NR'­CO2-R'', -CO2R'', -COR'''-NR'-CO-R''',-CONR'R'',SO2NR'R'',SO2R'''and -O-(CH2)n-R''' substituents, wherein n is from 0 to 4, each R’is the same or different and is hydrogen or C1-C6 alkyl, each R'' is the same or different and is hydrogen, C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, each R''' is the same or different and is C1-C6 alkyl, C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heteroaryl, and each R'''' is the same or different and is C6-C10 aryl, 5- to 10- membered heterocyclyl or 5- to 10- membered heterocryl, the aryl, heteroaryl, heterocyclyl and carbocyclyl moieties in said substituents being unsubstituted or substituted by a further substituent selected from C1-C4 alkyl, C1-C4 hydroxyalkyl and C1-C4 haloalkyl groups.

  式(I)的吡唑啉衍生物，或其药用可接受的盐，被发现对丙型肝炎感染具有活性，其中：R1为C6-C10芳基，5-到10-成员杂芳基，-(C1-C4烷基)-(C6-C10芳基)或-(C1-C4烷基)-(5-到10-成员杂芳基)；R2为C6-C10芳基，C3-C6碳环烷基，5-到10-成员杂芳基或5-到10-成员杂环烷基基团，该基团可选择地与C6-C10芳基，C3-C6碳环烷基，5-到10-成员杂芳基或5-到10-成员杂环烷基环融合；X为-NR'-，-NR'-CO-NR''-，-NR'-L，或-NR'-CO-L-，其中R'和R''相同或不同，分别代表氢或C1-C6烷基，L代表C1-C6烷基基团，R1和R2取代基中的芳基，杂芳基，杂环烷基和碳环烷基基团未取代或通过1、2或3个卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、氰基、硝基、C6-C10芳基、C3-C6碳环烷基、5-到10-成员杂环烷基、5-到10-成员杂芳基、-NR'-CO2-R''、-CO2R''、-COR'''-NR'-CO-R'''、-CONR'R''、SO2NR'R''、SO2R'''和-O-(CH2)n-R'''取代。
• 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.
• Solvent-free mechanochemical chlorination of pyrazoles with trichloroisocyanuric acid
  作者：Chi-Min Chen、Jia-Xin Chen、Ching Tat To

  DOI：10.1039/d3gc00170a

  日期：——

  A solvent-free, rapid and operationally simple method for the chlorination of pyrazoles with trichloroisocyanuric acid to access 4-chloropyrazole derivatives is described. This high-yielding protocol avoids tedious column chromatography and reduces solvent consumption. Mechanistic studies suggested an electrophilic aromatic substitution mechanism. This system also gives good green chemistry metrics

  描述了一种无溶剂、快速且操作简单的方法，用于用三氯异氰尿酸氯化吡唑以获得 4-氯吡唑衍生物。这种高产方案避免了繁琐的柱层析并减少了溶剂消耗。机理研究表明亲电子芳族取代机制。该系统还提供了良好的绿色化学指标。