4-Isopropyl-2-phenyl-4-(2,2,2-trifluoro-acetyl)-4H-oxazol-5-one | 106942-36-3

• 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-Isopropyl-2-phenyl-4-(2,2,2-trifluoro-acetyl)-4H-oxazol-5-one
• CAS: 106942-36-3
• 化学式: C₁₄H₁₂F₃NO₃
• 分子量: 299.249
• InChiKey: RNASTRGOKCOALU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-Isopropyl-2-phenyl-4-(2,2,2-trifluoro-acetyl)-4H-oxazol-5-one 在 N-甲基吗啉 、 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 草酸 、 二甲基亚砜 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.75h， 生成 N-<<5-(dimethylamino)-1-naphtalenyl>sulfonyl>-L-alanyl-L-alanyl-N-<3,3,3-trifluoro-1-(1-methylethyl)-2-oxopropyl>-L-prolinamide
  参考文献：
  名称：

  Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G

  摘要：

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.

  DOI：

  10.1021/jm00163a063
• 作为产物：
  描述：

  N-苯甲酰-N-缬氨酸 在 乙酸酐 作用下， 生成 4-Isopropyl-2-phenyl-4-(2,2,2-trifluoro-acetyl)-4H-oxazol-5-one
  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

• Base-catalysed ¹⁸F-labelling of trifluoromethyl ketones. Application to the synthesis of ¹⁸F-labelled neutrophil elastase inhibitors
  作者：Denise N. Meyer、Miguel A. Cortés González、Xingguo Jiang、Linus Johansson-Holm、Monireh Pourghasemi Lati、Mathias Elgland、Patrik Nordeman、Gunnar Antoni、Kálmán J. Szabó

  DOI：10.1039/d1cc03624f

  日期：——

  A new method for the fluorine-18 labelling of trifluoromethyl ketones has been developed. This method is based on the conversion of a–COCF3 functional group to a difluoro enol silyl ether followed by halogenation and fluorine-18 labelling. The utility of this new method was demonstrated by the synthesis of fluorine-18 labelled neutrophil elastase inhibitors, which are potentially useful for detection

  开发了一种用于三氟甲基酮的氟 18 标记的新方法。该方法基于将 a-COCF 3官能团转化为二氟烯醇甲硅烷基醚，然后进行卤化和氟 18 标记。氟 18 标记的中性粒细胞弹性蛋白酶抑制剂的合成证明了这种新方法的实用性，这些抑制剂可能用于检测炎症性疾病。