4-trifluoroacetyl-5-hydroxy-2-phenyloxazole | 106942-35-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-trifluoroacetyl-5-hydroxy-2-phenyloxazole
• 英文别名: 2-phenyl-4-(2,2,2-trifluoroacetyl)-4H-oxazol-5-one；2-Phenyl-4-(trifluoroacetyl)-2-oxazoline-5-one；2-phenyl-4-(2,2,2-trifluoroacetyl)-4H-1,3-oxazol-5-one
• CAS: 106942-35-2
• 化学式: C₁₁H₆F₃NO₃
• 分子量: 257.169
• InChiKey: MLMPMCISMSVJRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  303.3±52.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-trifluoroacetyl-5-hydroxy-2-phenyloxazole 在 sodium acetate 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N-苯甲酰基甘氨酸甲酯
  参考文献：
  名称：

  4-Trifluoroacetyl-2-phenyloxazol-5-one: Versatile Template for Synthesis of Trifluoromethyl-Substituted Heterocycles

  摘要：

  4-Trifluoroacetyl-2-phenyloxazol-5-one (1) is a versatile template for the synthesis of various trifluoromethyl-substituted heterocycles. Cyclocondesation of 1 with hydroxylamine and hydrazine afforded isoxazole and pyrazole, respectively. Another key protocol involves nucleophilic ring opening of 1 with H2O or MeOH to give alpha-amido trifluoromethyl ketones which are transformed into trifluoromethyl-substituted thiazoles, oxazoles, imidazoles, pyrazoles, and pyrimidines.

  DOI：

  10.3987/com-13-12838
• 作为产物：
  描述：

  马尿酸 在 乙酸酐 作用下， 生成 4-trifluoroacetyl-5-hydroxy-2-phenyloxazole
  参考文献：
  名称：

  氟化α-氨基酮的合成第一部分：α-苯甲酰胺基烷基二氟和三氟甲基酮

  摘要：

  由α-氨基酸制得的2-苯基-5（4H）-恶唑酮通过改良的Dakin-West方法与二氟和三氟乙酸酐反应，以一锅法反应生成α-苯甲酰胺基烷基二氟和三氟甲基酮收率高。单氟甲基类似物也由α-氨基酸制备，但是避免了使用剧毒的氟乙酸酐。关键步骤是在相应的溴甲基酮上进行卤素交换反应。

  DOI：

  10.1016/s0040-4039(00)84319-1

文献信息

• Efficient synthesis of (R)-3-amino-1,1,1-trifluoropropan-2-ol via a Dakin–West reaction followed by enantioselective reduction
  作者：Lulin Wei、Teresa Makowski、Carlos Martinez、Arun Ghosh

  DOI：10.1016/j.tetasy.2008.12.001

  日期：2008.12

  chromatography-free asymmetric synthesis of (R)-3-amino-1,1,1-trifluoropropan-2-ol was developed for large scale production of a cholesterol ester transfer protein (CETP) inhibitor. The synthesis features a new efficient route to a β-amino trifluoromethylketone involving a modified Dakin–West reaction followed by an asymmetric hydrogenation or an enzymatic reduction of the resulting ketone to the alcohol.

  开发了一种高效，无色谱的不对称合成（R）-3-氨基-1,1,1-三氟丙烷-2-醇的方法，用于大规模生产胆固醇酯转移蛋白（CETP）抑制剂。合成的特征是一种新的有效途径来生产β-氨基三氟甲基酮，涉及经过修饰的Dakin-West反应，然后进行不对称氢化或将所得酮酶解为醇。
• [EN] IMIDAZO[1,2-B]PYRIDAZINE IL-17A INHIBITORS<br/>[FR] INHIBITEURS IMIDAZO [1,2-B]PYRIDAZINE IL-17 A
  申请人：LILLY CO ELI

  公开号：WO2020146194A1

  公开（公告）日：2020-07-16

  The invention provides certain difluorocyclohexyl-imidazopyridazinyl-imidazolidinone compounds of formula II as IL-17A inhibitors, pharmaceutical compositions thereof, and methods of using a compound of formula II to treat certain symptoms of psoriasis, rheumatoid arthritis or multiple sclerosis.

  该发明提供了某些二氟环己基咪唑吡啶啉咪唑烷酮化合物（式II）作为IL-17A抑制剂，以及它们的药物组合物，并使用式II化合物治疗银屑病、类风湿性关节炎或多发性硬化症某些症状的方法。
• IL-17A INHIBITORS
  申请人：Eli Lilly and Company

  公开号：US20220073526A1

  公开（公告）日：2022-03-10

  The invention provides certain difluorocyclohexyl-imidazopyridazinyl-imidazolidinone compounds of formula II as IL-17A inhibitors, pharmaceutical compositions thereof, and methods of using a compound of formula II to treat certain symptoms of psoriasis, rheumatoid arthritis or multiple sclerosis.
• Synthesis of fluorinated α-amino ketones part I: α-benzamidoalkyl mono- di- and trifluoromethyl ketones
  作者：Michael Kolb、Jacqueline Barth、Bernhard Neises

  DOI：10.1016/s0040-4039(00)84319-1

  日期：1986.1

  2-Phenyl-5(4H)-oxazolones, obtained from α-amino acids, are reacted with di- and trifluoro acetic anhydride by a modified Dakin-West procedure to yield in a one-pot reaction α-benzamidoalkyl-di- and trifluoromethyl ketones in good yields. The monofluoromethyl analogues were also prepared from α-amino acids, however the use of the highly toxic fluoroacetic anhydride was avoided. The key step is the

  由α-氨基酸制得的2-苯基-5（4H）-恶唑酮通过改良的Dakin-West方法与二氟和三氟乙酸酐反应，以一锅法反应生成α-苯甲酰胺基烷基二氟和三氟甲基酮收率高。单氟甲基类似物也由α-氨基酸制备，但是避免了使用剧毒的氟乙酸酐。关键步骤是在相应的溴甲基酮上进行卤素交换反应。
• 4-Trifluoroacetyl-2-phenyloxazol-5-one: Versatile Template for Synthesis of Trifluoromethyl-Substituted Heterocycles
  作者：Masami Kawase、Ryosuke Saijo、Ken-ichi Kurihara

  DOI：10.3987/com-13-12838

  日期：——

  4-Trifluoroacetyl-2-phenyloxazol-5-one (1) is a versatile template for the synthesis of various trifluoromethyl-substituted heterocycles. Cyclocondesation of 1 with hydroxylamine and hydrazine afforded isoxazole and pyrazole, respectively. Another key protocol involves nucleophilic ring opening of 1 with H2O or MeOH to give alpha-amido trifluoromethyl ketones which are transformed into trifluoromethyl-substituted thiazoles, oxazoles, imidazoles, pyrazoles, and pyrimidines.