5-三氯甲基异恶唑 | 88283-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-三氯甲基异恶唑
• 中文别名: 5-三氯甲基异噁唑
• 英文名称: 5-trichloromethyl isoxazole
• 英文别名: 5-Trichloromethylisoxazole；5-trichloromethyl-isoxazole；5-(trichloromethyl)-1,2-oxazole
• CAS: 88283-10-7
• 化学式: C₄H₂Cl₃NO
• mdl: MFCD18449654
• 分子量: 186.425
• InChiKey: LJVSHTQXMKTCBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-三氯甲基异恶唑 在 硫酸 作用下， 生成 异唑-5-羧酸
  参考文献：
  名称：

  A convenient one-pot synthesis of 5-carboxyisoxazoles: trichloromethyl group as a carboxyl group precursor

  摘要：

  The one-pot synthesis of ten 5-carboxyisoxazoles from the cyclocondensation of beta-alkoxyvinyl trichloromethyl ketones [CCl3C(O)C(R-2)=C(R-1)OR, where R-1, R-2=H, Me and R=Me, Et] and 2-trichloroacetyl cyclohexanone with hydroxylamine is reported. This work shows that the trichloromethyl group attached to beta-alkoxyvinyl trichloromethyl ketones (a heterocyclic CCC building block) is an excellent carboxyl group precursor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02047-x
• 作为产物：
  描述：

  (3E)-1,1,1-三氯-4-乙氧基-3-丁烯-2-酮 在 硫酸 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以85%的产率得到5-三氯甲基异恶唑
  参考文献：
  名称：

  A convenient one-pot synthesis of 5-carboxyisoxazoles: trichloromethyl group as a carboxyl group precursor

  摘要：

  The one-pot synthesis of ten 5-carboxyisoxazoles from the cyclocondensation of beta-alkoxyvinyl trichloromethyl ketones [CCl3C(O)C(R-2)=C(R-1)OR, where R-1, R-2=H, Me and R=Me, Et] and 2-trichloroacetyl cyclohexanone with hydroxylamine is reported. This work shows that the trichloromethyl group attached to beta-alkoxyvinyl trichloromethyl ketones (a heterocyclic CCC building block) is an excellent carboxyl group precursor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02047-x

文献信息

• Eine einfache Synthese von Isoxazol-5-carbonsäure
  作者：Wolfgang Spiegler、Norbert Götz

  DOI：10.1055/s-1986-31481

  日期：——

  A Simple Synthesis of Isoxazole-5-carboxylic Acid Isoxazole-5-carboxylic acid is prepared from trichloroacetyl chloride, ethyl vinyl ether, and hydroxylamine. The intermediates 5-hydroxy-5-trichloromethyl-2-isoxazoline and 5-trichloromethylisoxazole can be isolated. The reaction of 5-trichloromethylisoxazole with trichloroacetic acid leads to isoxazole-5-carboxylic acid chloride and trichloroacetyl chloride.

  异噁唑-5-羧酸的简单合成方法 异噁唑-5-羧酸由三氯乙酰氯、乙烯基乙醚和羟胺制备而成。中间产物 5-羟基-5-三氯甲基-2-异噁唑啉和 5-三氯甲基异噁唑可以分离出来。5-三氯甲基异噁唑与三氯乙酸反应可生成异噁唑-5-羧酰氯和三氯乙酰氯。
• Flourine-containing 5-trihalogenomethyl-isoxazoles and a process for
  申请人：Bayer Aktiengesellschaft

  公开号：US04888430A1

  公开（公告）日：1989-12-19

  The present invention relates to new 5-trihalogenomethyl-isoxazoles of the formula (I) ##STR1## in which x represents 1, 2 or 3, and a process for their preparation by reacting the corresponding trichloromethylisoxazole with a fluorinating agent.

  本发明涉及公式（I）的新型5-三卤甲基异噁唑物，其中x表示1、2或3，并且通过将相应的三氯甲基异噁唑与氟化剂反应来制备它们的方法。
• Fluor enthaltende 5-Trihalogenmethyl-isoxazole und ein Verfahren zu deren Herstellung
  申请人：BAYER AG

  公开号：EP0270963A1

  公开（公告）日：1988-06-15

  Die vorliengende Erfindung betrifft neue 5-Trihalogen-­methyl-isoxazole der Formel (I) in der x für 1, 2 oder 3 steht und ein Verfahren zu deren Herstellung durch Umsetzung des entsprechenden Tri­chlormethylisoxazols mit einem Fluorierungsmittel.

  本发明涉及式（I）中 x 为 1、2 或 3 的新型 5-三卤甲基异噁唑，以及通过相应的三氯甲基异噁唑与氟化剂反应制备它们的工艺。
• 3-Halogenalkyl-1-aryl-pyrazole
  申请人：BAYER AG

  公开号：EP0285947A2

  公开（公告）日：1988-10-12

  Es werden neue 3-Halogenalkyl-1-aryl-pyrazole der all­gemeinen Formel (I) bereitgestellt, in welcher R¹ für Halogenalkyl steht, R² für Cyano, für Hydroxycarbonyl, für Carbamoyl, Thiocarbamoyl, für Alkoxycarbonyl, N-Alkylcarba­moyl, N,N-Dialkylcarbamoyl, für Alkenyloxycarbo­nyl, N-Alkenylcarbamoyl, N,N-Dialkenylcarbamoyl, für Alkinyloxycarbonyl, N-Alkinylcarbamoyl, N,N-­Dialkinylcarbamoyl, N-Arylcarbamoyl, für Alkyl­carbonyl, Halogenalkylcarbonyl oder Cycloalkyl­carbonyl steht, R³ für Wasserstoff, Alkyl, Halogenalkyl oder Cyclo­alkyl steht und Ar für substituiertes Phenyl mit Ausnehme des 2,4-­Dinitrophenylrestes steht. Die neuen Verbindungen (I) besitzen eine stark ausge­prägte Wirksamkeit gegen tierische Schädlingen, insbeson­dere gegen Insekten.

  提供了通式为(I)的新型 3-卤代烷基-1-芳基吡唑 提供、 其中 R¹ 代表卤代烷基、 R²代表氰基、羟基羰基、氨基甲酰基、硫代氨基甲酰基、烷氧羰基、N-烷基氨基甲酰基、N,N-二烷基氨基甲酰基、烯氧羰基、N-烯基氨基甲酰基、N、N-炔氧羰基、N-炔基氨基甲酰基、N,N-二炔基氨基甲酰基、N-芳基氨基甲酰基、烷基羰基、卤代烷基羰基或环烷基羰基、 R³ 是氢、烷基、卤代烷基或环烷基，以及 Ar 是取代的苯基，但 2,4-二硝基苯基除外。 新化合物（I）对动物害虫，特别是昆虫有很好的防治效果。
• Synthesis in Water and Antimicrobial Activity of 5-Trichloromethyl-4,5-dihydroisoxazoles
  作者：Alex F. C. Flores、Luciana A. Piovesan、Alynne A. Souto、Mariano A. Pereira、Marcos A. P. Martins、Tatiane L. Balliano、Givanildo S. da Silva

  DOI：10.1080/00397911.2012.706349

  日期：2013.9.2

  Two series of 5-trichloromethylisoxazoles were synthesized from the cyclocondensation of 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl3CC(O)C(R-2)=C(R-1)OMe, where R-1=H, Me, Et, Pr, iso-Pr, cyclo-Pr, Bu, terc-Bu, CH2Br, CHBr2, CH(Me)SMe, (CH2)(2)Ph, and Ph, and R-2=H; R-1=H and R-2=Me and Et; R-1 and R-2=-(CH2)(4)- and -(CH2)(5)-; and R-1=Et and Ph and R-2=Me] with hydroxylamine hydrochloride through a rapid one-pot reaction in water. The 5-trichloromethyl-4,5-dihydroisoxazoles were aromatized by reaction with concentrated sulfuric acid to obtain the respective 5-trichloromethylisoxazoles. Their structures were confirmed by elemental analysis, H-1/C-13 nuclear magnetic resonance, and electron impact mass spectroscopy. Crystal structure analysis for 5-triclhoromethyl-5-hydroxy-3-propyl-4,5-dihydroisoxazole (2d) and 5-trichloromethyl-5-hydroxy-3,4-hexamethylene-4,5-dihydroisoxazole (2o) is presented. The antimicrobial activities of the 5-trichloromethyl-4,5-dihydroisoxazole derivatives were examined using the standard twofold dilution method against Gram-positive bacteria (Staphylococcus aureus), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and yeasts (Candida spp. and Cryptococcus neoformans). All of the tested 5-trichloromethyldihydroisoxazoles exhibited antibacterial and antifungal activities at the tested concentrations. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

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