methyl 4-phenyl-2-(trifluoromethyl)oxazole-5-carboxylate | 1346526-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 4-phenyl-2-(trifluoromethyl)oxazole-5-carboxylate
• 英文别名: methyl 4-phenyl-2-(trifluoromethyl)-1,3-oxazole-5-carboxylate
• CAS: 1346526-79-1
• 化学式: C₁₂H₈F₃NO₃
• 分子量: 271.196
• InChiKey: SRNNEIRAZXIFPE-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C
• 沸点：
  306.9±42.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 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：
  7

反应信息

• 作为产物：
  描述：

  methyl 3-amino-3-phenylacrylate 、 [双(三氟乙酰氧基)碘]苯 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以80%的产率得到methyl 4-phenyl-2-(trifluoromethyl)oxazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of 2-(Trifluoromethyl)oxazoles from β-Monosubstituted Enamines via PhI(OCOCF₃)₂-Mediated Trifluoroacetoxylation and Cyclization

  摘要：

  Treatment of beta-monosubstituted enamines with phenyliodine bis(trifluoroacetate) (PIFA) was found to give a variety of 4,5-disubstituted 2-(trifluoromethyl)oxazoles. This approach allows the incorporation of the trifluoromethyl moiety in PIFA into the final products, which presumably takes place via the oxidative beta-trifluoroacetoxylation of the enamine substrates followed by subsequent intramolecular cyclization.

  DOI：

  10.1021/jo202070h

文献信息

• Synthesis of 2-Fluoroalkylated Oxazoles from β-Monosubstituted Enamines <i>via</i> Fluoroacyloxylation and Cyclization Mediated by Fluoroalkyl-Containing Hypervalent Iodine(III) Species Generated <i>In Situ</i>
  作者：Zhifang Yang、Fengxia Sun、Yadong Li、Kaiyue Yang、Jianing Zhang、Lingzhi Xu、Hui Zhao、Yunfei Du

  DOI：10.1021/acs.joc.3c01032

  日期：2023.8.4

  A metal-free synthesis of a series of fluoroalkyl-containing oxazoles from β-monosubstituted enamines was developed. This fluoroacyloxylation/cyclization cascade process was mediated by fluoroalkyl-containing hypervalent iodine(III) species formed in situ from the reaction of phenyliodine(III) diacetate (PIDA) and RCF2CO2H (R = H, Cl, Br, F, CF3, CH3, Ph, SAr, OAr).

  开发了由β-单取代烯胺无金属合成一系列含氟烷基恶唑的方法。这种氟酰氧基化/环化级联过程是由二乙酸苯碘(III) (PIDA) 和 RCF 2 CO 2 H (R = H, Cl, Br, F, CF 3、CH 3、Ph、SAr、OAr)。