5-methyl-3-(4-trifluoromethylphenyl)isoxazole-4-formic acid | 943130-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methyl-3-(4-trifluoromethylphenyl)isoxazole-4-formic acid
• 英文别名: 3-(4-trifluoromethyl-phenyl)-5-methyl-isoxazole-4-carboxylic acid；5-Methyl-3-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxylic acid
• CAS: 943130-82-3
• 化学式: C₁₂H₈F₃NO₃
• mdl: MFCD07376124
• 分子量: 271.196
• InChiKey: AQMLVWABNFLPPA-UHFFFAOYSA-N

物化性质

• 沸点：
  351.7±37.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(4-trifluoromethylphenyl)isoxazole-4-formic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-(4-(5-methyl-3-(4-(trifluoromethyl)phenyl)isoxazole-4-carbonyl)piperazine-1-carbonyl)-2H-chromen-2-one
  参考文献：
  名称：

  Design, Synthesis, andIn VitroEvaluation of Novel 3, 7-Disubstituted Coumarin Derivatives as Potent Anticancer Agents

  摘要：

  Twenty‐seven 3, 7‐disubstituted coumarin derivatives were designed, synthesized, and evaluated in vitro as anticancer agents. Most of the compounds showed moderate‐to‐potent antiproliferative activity against K562 cells. Compounds 7b and 7d were chosen to evaluate the concentration of 50% growth inhibition (GI50) against SN12C, OVCAR, BxPC‐3, KATO‐III, T24, SNU‐1, WiDr, HeLa, K562, and AGS cell lines. The most potent compound 7d was selected for further cell cycle arrest assay in the AGS cell line. The in vitro data indicated that methylation of benzimidazole moiety at the 3‐position of coumarin exhibited significant enhancement of anticancer activity. This study should provide important information for further modification and optimization of coumarin derivatives as anticancer agents.

  DOI：

  10.1111/cbdd.12531
• 作为产物：
  描述：

  4-(trifluoromethyl)benzaldehyde oxime 在 盐酸 、 N-氯代丁二酰亚胺 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.75h， 生成 5-methyl-3-(4-trifluoromethylphenyl)isoxazole-4-formic acid
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives

  摘要：

  A series of unique 3-aryl-5-(haloalkyl)-4-isoxazolecarboxamides have been prepared which exhibit, in both greenhouse and field studies, significant preemergent and postemergent herbicidal activity in the grams per hectare range against broadleaf and narrowleaf weeds. The key step in the formation of the fully substituted isoxazole ring 2 is 1,3 dipolar cycloaddition of a haloalkyl-substituted acetylenic ester and a nitrile oxide intermediate. The 3-aryl-5-(halo alkyl)-4-isoxazolecarboxylate esters 2 are converted to isoxazole-4-carboxamide herbicides 5 and 6, secondary amides 7, and amino acid derivatives 8. Greatest activity was observed with compounds having a combination of three substituents: a substituted phenyl ring in the 3-position, a primary or secondary carboxamide in the 4-position, and a difluorochloromethyl group in the, 5-position of the isoxazole ring.

  DOI：

  10.1021/jf00049a040

文献信息

• Ultrasound-assisted synthesis and preliminary bioactivity of novel 2H-1,2,4-thiadiazolo[2,3-a]pyrimidine derivatives containing fluorine
  作者：Mao Rong Wang、Lin Jiang、Shao Fang Zhou、Ze Yuan Zhang、Zeng Chen Ji

  DOI：10.1016/j.cclet.2012.03.005

  日期：2012.5

  Eight novel 5,7-disubstituted-2-5-methyl-3-(4-trifluoromethylphenyl)isoxazol-4-ylcarbonylimin} -2H-1,2,4-thiadiazolo[2,3-a]pyrimidines were synthesized by multi-step reactions in yields 68-85%. Reactions were carried out either by ultrasound irradiation or conventional method, and found it was faster and more efficient under ultrasonic irradiation. Preliminary herbicidal activities against Echinochloa crus-galli, Digitaria sanguinalis and Chenopodium serotinum were also evaluated by flat-utensil method, and the results indicated that the target compounds exhibited significant activities, some were even higher than the control herbicide. (C) 2012 Lin Jiang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.