Methyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate | 159693-09-1

• 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: Methyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 159693-09-1
• 化学式: C₁₂H₁₀FNO₃
• 分子量: 235.215
• InChiKey: JTXOFNWDTGMOHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate 在 盐酸 、 ammonium hydroxide 、 草酰氯 、 sodium carbonate 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 73.25h， 生成 3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid amide
  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
• 作为产物：
  描述：

  syn-4-氟苯甲醛肟 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 Methyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate
  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

• Novel ortho-terphenyl inhibitors of p38 kinase and methods of treating inflammatory disorders
  申请人：Severance L. Daniel

  公开号：US20060252807A1

  公开（公告）日：2006-11-09

  The present invention relates to compounds and methods useful as inhibitors of p38 kinase for the treatment or prevention and treatment of diseases such as inflammatory diseases, autoimmune diseases, destructive bone disorders, proliferative disorders, angiogenic disorders, infectious diseases, neurodegenerative diseases, and viral diseases.

  本发明涉及化合物和方法，用于作为p38激酶抑制剂的治疗或预防和治疗炎症性疾病、自身免疫性疾病、破坏性骨疾病、增殖性疾病、血管生成性疾病、传染病、神经退行性疾病和病毒性疾病的药物。
• ORTHO-TERPHENYL INHIBITORS OF P38 KINASE AND METHODS OF TREATING INFLAMMATORY DISORDERS
  申请人：Kalypsys, Inc.

  公开号：EP1871770A1

  公开（公告）日：2008-01-02
• [EN] ORTHO-TERPHENYL INHIBITORS OF P38 KINASE AND METHODS OF TREATING INFLAMMATORY DISORDERS<br/>[FR] INHIBITEURS ORTHO-TERPHENYLE DE KINASE P38 ET PROCEDES DE TRAITEMENT DES TROUBLES INFLAMMATOIRES
  申请人：KALYPSYS INC

  公开号：WO2006116355A1

  公开（公告）日：2006-11-02

  [EN] The present invention relates to compounds and methods useful as inhibitors of p38 kinase for the treatment or prevention and treatment of diseases such as inflammatory diseases, autoimmune diseases, destructive bone disorders, proliferative disorders, angiogenic disorders, infectious diseases, neurodegenerative diseases, and viral diseases.
  [FR] La présente invention se rapporte à des composés et à des procédés utiles comme inhibiteurs de la kinase p38 pour le traitement ou la prévention et le traitement de maladies telles que les maladies inflammatoires, les maladies auto-immunes, les troubles destructeurs de l'os, les troubles proliférateurs, les troubles angiogéniques, les maladies infectieuses, les maladies neurodégénératives et les maladies virales.
• Synthesis and Herbicidal Activity of 3-Aryl-5-(haloalkyl)-4-isoxazolecarboxamides and Their Derivatives
  作者：Bruce C. Hamper、Kindrick L. Leschinsky、Steven S. Massey、Crystal L. Bell、Lawrence H. Brannigan、S. Douglas Prosch

  DOI：10.1021/jf00049a040

  日期：1995.1

  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.