dimethyl 2-phenyl-5-(trifluoromethyl)furan-3,4-dicarboxylate | 1333158-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: dimethyl 2-phenyl-5-(trifluoromethyl)furan-3,4-dicarboxylate
• 英文别名: 2-(Trifluoromethyl)-5-phenylfuran-3,4-dicarboxylic acid dimethyl ester
• CAS: 1333158-60-3
• 化学式: C₁₅H₁₁F₃O₅
• 分子量: 328.245
• InChiKey: QQJNVBUUPPEDOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  dimethyl (2E)-2-benzoylbut-2-enedioate 、 三氟乙酸酐 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到dimethyl 2-phenyl-5-(trifluoromethyl)furan-3,4-dicarboxylate
  参考文献：
  名称：

  A Powerful Cascade Approach for Expeditious Synthesis of Trifluoromethylated Furans

  摘要：

  A powerful approach to synthesize trifluoromethylated furans has been developed. The method is operationally simple, broad in substrate scope, and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize trifluoromethylated furans but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.

  DOI：

  10.1021/ol2022092

文献信息

• Formal [2+2+1] Synthesis of Tetrasubstituted Furans from Aldehydes, Acetylenedicarboxylates, and Acyl Compounds
  作者：Keiichiro Tateishi、Yuri Matsumoto、Akio Saito

  DOI：10.1002/ejoc.201900806

  日期：2019.9.8

  A combination of 4‐picoline and Ph3P (or nBu3P) efficiently promotes a formal [2+2+1] synthesis of tetrasubstituted furans from aldehydes, acetylenedicarboxylates and acyl compounds through O‐acylation of the α,β‐enone intermediates followed by intramolecular Wittig reaction under the metal‐free and mild conditions. The present method can be applied not only to acyl chlorides but also trifluoroacetic

  4-甲基吡啶和Ph 3 P（或n Bu 3 P）的组合有效地促进了α，β-烯酮的O-酰化作用由醛，炔二羧酸酯和酰基化合物从四价呋喃[2 + 2 + 1]形式正式合成中间体，然后在无金属和温和条件下进行分子内Wittig反应。本方法不仅可以应用于酰氯，而且可以作为酰基化合物应用于三氟乙酸酐。
• A Powerful Cascade Approach for Expeditious Synthesis of Trifluoromethylated Furans
  作者：Yao Wang、Yong-Chun Luo、Xiu-Qin Hu、Peng-Fei Xu

  DOI：10.1021/ol2022092

  日期：2011.10.7

  A powerful approach to synthesize trifluoromethylated furans has been developed. The method is operationally simple, broad in substrate scope, and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize trifluoromethylated furans but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.