ethyl 4-hydroxy-2-(4-methoxyphenyl)-4-trifluoromethyl-4,5-dihydrooxazole-5-carboxylate | 1354700-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 4-hydroxy-2-(4-methoxyphenyl)-4-trifluoromethyl-4,5-dihydrooxazole-5-carboxylate
• 英文别名: ethyl 4-hydroxy-2-(4-methoxyphenyl)-4-(trifluoromethyl)-5H-1,3-oxazole-5-carboxylate
• CAS: 1354700-08-5
• 化学式: C₁₄H₁₄F₃NO₅
• 分子量: 333.264
• InChiKey: OFNDMWAZERKWCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-2-(4-methoxyphenyl)-4-trifluoromethyl-4,5-dihydrooxazole-5-carboxylate 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以72%的产率得到ethyl 2-(4-methoxyphenyl)-4-trifluoromethyloxazole-5-carboxylate
  参考文献：
  名称：

  Diverse Trifluoromethyl Heterocycles from a Single Precursor

  摘要：

  Ethyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate is a highly versatile intermediate for the synthesis of a wide range of trifluoromethyl heterocycles. With the use of rhodium(II) or copper(II) catalyzed carbene X-H insertion reactions as key steps, a diverse set of trifluoromethyl-oxazoles, -thiazoles, -imidazoles, -1,2,4-triazines, and -pyridines are available from the diazoketoester, either directly in a single step or with just one additional step.

  DOI：

  10.1021/jo202201w
• 作为产物：
  描述：

  4-甲氧基苯甲酰胺 、 ethyl 2-diazo-3-oxo-4,4,4-trifluorobutyrate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以38%的产率得到ethyl 4-hydroxy-2-(4-methoxyphenyl)-4-trifluoromethyl-4,5-dihydrooxazole-5-carboxylate
  参考文献：
  名称：

  Diverse Trifluoromethyl Heterocycles from a Single Precursor

  摘要：

  Ethyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate is a highly versatile intermediate for the synthesis of a wide range of trifluoromethyl heterocycles. With the use of rhodium(II) or copper(II) catalyzed carbene X-H insertion reactions as key steps, a diverse set of trifluoromethyl-oxazoles, -thiazoles, -imidazoles, -1,2,4-triazines, and -pyridines are available from the diazoketoester, either directly in a single step or with just one additional step.

  DOI：

  10.1021/jo202201w

文献信息

• Diverse Trifluoromethyl Heterocycles from a Single Precursor
  作者：Mark A. Honey、Raffaele Pasceri、William Lewis、Christopher J. Moody

  DOI：10.1021/jo202201w

  日期：2012.2.3

  Ethyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate is a highly versatile intermediate for the synthesis of a wide range of trifluoromethyl heterocycles. With the use of rhodium(II) or copper(II) catalyzed carbene X-H insertion reactions as key steps, a diverse set of trifluoromethyl-oxazoles, -thiazoles, -imidazoles, -1,2,4-triazines, and -pyridines are available from the diazoketoester, either directly in a single step or with just one additional step.