1-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-1-methyl-5-(trifluoromethyl)-1H-pyrazole | 142623-48-1

• 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-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-1-methyl-5-(trifluoromethyl)-1H-pyrazole
• 英文别名: 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole；1-methyl-3-[4-chloro-2-fluoro-5-methyl-phenyl-1-yl]-5-trifluoromethyl-pyrazole；3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-(trifluoromethyl)pyrazole
• CAS: 142623-48-1
• 化学式: C₁₂H₉ClF₄N₂
• 分子量: 292.663
• InChiKey: YNQXHQDFBVIEDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-1-methyl-5-(trifluoromethyl)-1H-pyrazole 在 ammonium hydroxide 、 草酰氯 、 溴 、 cobalt(II) acetate 、 manganese(II) acetate 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 61.0h， 生成 JV 485 (14C-Ph) amide
  参考文献：
  名称：

  The radiolabeled syntheses of JV 485, a herbicide candidate for winter wheat

  摘要：

  JV 485 [C-14-Ph] and JV 485 [C-14-Py] were synthesized in seven steps in 35% and 44% overall yields, respectively, utilizing the same reaction schemes. The key step in each of the syntheses is a one pot Mid-Century Oxidation (I) of an aromatic methyl group to a carboxylic acid. The C-14 radiolabeled syntheses of two isolated metabolites of JV 485 were also completed. Preparation of the JV 485 [phenyl-C-14(U)] amide was completed in 62% yield from 2-chloro-5-14-bromo-1-methyl-5-trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid [ring-C-14(U)], (9) over bar. Preparation of the JV 485 [phenyl-C-14(U)] desmethyl acid <(13)over bar> was accomplished in 18% overall yield in four steps from 3-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-5-(trifluoromethyl)1H-pyrazole, (4) over bar.

  DOI：

  10.1002/1099-1344(200006)43:7<645::aid-jlcr349>3.0.co;2-6
• 作为产物：
  描述：

  4-氯-2-氟-5-甲基苯乙酮 在 sodium methylate 、 肼 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 13.5h， 生成 1-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-1-methyl-5-(trifluoromethyl)-1H-pyrazole
  参考文献：
  名称：

  The radiolabeled syntheses of JV 485, a herbicide candidate for winter wheat

  摘要：

  JV 485 [C-14-Ph] and JV 485 [C-14-Py] were synthesized in seven steps in 35% and 44% overall yields, respectively, utilizing the same reaction schemes. The key step in each of the syntheses is a one pot Mid-Century Oxidation (I) of an aromatic methyl group to a carboxylic acid. The C-14 radiolabeled syntheses of two isolated metabolites of JV 485 were also completed. Preparation of the JV 485 [phenyl-C-14(U)] amide was completed in 62% yield from 2-chloro-5-14-bromo-1-methyl-5-trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid [ring-C-14(U)], (9) over bar. Preparation of the JV 485 [phenyl-C-14(U)] desmethyl acid <(13)over bar> was accomplished in 18% overall yield in four steps from 3-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-5-(trifluoromethyl)1H-pyrazole, (4) over bar.

  DOI：

  10.1002/1099-1344(200006)43:7<645::aid-jlcr349>3.0.co;2-6

文献信息

• A General and Regioselective Synthesis of 5-Trifluoromethyl-pyrazoles
  作者：Robert S. Foster、Harald Jakobi、Joseph P. A. Harrity

  DOI：10.1021/ol3021918

  日期：2012.9.21

  Two synthetic approaches to 4-trifluoromethylsydnones, a novel class of these mesoionic reagents, are reported. These compounds undergo regioselective alkyne cycloaddition reactions, thereby providing a general approach to 5-trifluoromethylpyrazoles. This method has been employed in a short formal synthesis of the herbicide fluazolate.

  报道了两种合成方法4-三氟甲基sydnones，这些新的一类这类中性离子试剂。这些化合物进行区域选择性炔烃环加成反应，从而为5-三氟甲基吡唑提供了一种通用方法。该方法已用于除草剂氟唑酸盐的短形式合成中。
• [EN] PHENYLISOXAZOLINE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ DE PHÉNYLISOXAZOLINE ET SON UTILISATION<br/>[ZH] 一种苯基异恶唑啉类化合物及其用途
  申请人：SHENYANG SINOCHEM AGROCHEMICALS R & D CO LTD

  公开号：WO2021082901A1

  公开（公告）日：2021-05-06

  提供了一种苯基异恶唑啉类化合物及其用途。苯基异恶唑啉类化合物如通式(I)所示，通式(I)化合物具有很好的除草活性，可以有效地控制稗草、狗尾草、异型莎草、水莎草、马唐、荩草、苘麻、百日草、反枝苋、马齿苋、苍耳、龙葵、决明、野西瓜苗、野大豆等杂草，在低剂量下就可以获得很好的除草效果，且对作物如玉米、小麦、水稻等具有一定的安全性，在农业上可用作除草剂。
• HERBICIDAL SUBSTITUTED ARYL-HALOALKYLPYRAZOLES
  申请人：MONSANTO COMPANY

  公开号：EP0553307B1

  公开（公告）日：1998-12-09
• HETEROCYCLIC- AND CARBOCYCLIC-SUBSTITUTED BENZOIC ACIDS AND SYNTHESIS THEREOF
  申请人：MONSANTO COMPANY

  公开号：EP0772598A1

  公开（公告）日：1997-05-14
• PREPARATION OF HETEROCYCLIC- AND CARBOCYCLIC-SUBSTITUTED BENZOIC ACIDS
  申请人：Monsanto Technology LLC

  公开号：EP0772598B1

  公开（公告）日：2002-02-06