4-hydroxy-1-methyl-3-(2,2,2-trifluoroacetyl)quinolin-2(1H)-one | 73281-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-hydroxy-1-methyl-3-(2,2,2-trifluoroacetyl)quinolin-2(1H)-one
• 英文别名: 4-hydroxy-1-methyl-3-trifluoroacetylquinolin-2(1H)-one；4-hydroxy-1-methyl-3-trifluoroacetyl-1H-quinolin-2-one；4-Hydroxy-1-methyl-3-(2,2,2-trifluoroacetyl)quinolin-2-one
• CAS: 73281-60-4
• 化学式: C₁₂H₈F₃NO₃
• 分子量: 271.196
• InChiKey: AFEPAUBAOOEFFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-2-cyano-4,4,4-trifluoro-3-hydroxy-N-methyl-N-phenylbut-2-enamide 在 N,N-二甲基甲酰胺 、 三氟乙酸酐 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以89%的产率得到4-hydroxy-1-methyl-3-(2,2,2-trifluoroacetyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Trifluoroacetylation-Induced Houben−Hoesch-Type Cyclization of Cyanoacetanilides: Increased Nucleophilicity of CN Groups

  摘要：

  Trifluoroacetic anhydride-mediated tandem trifluoroacetylation/cyclization of cyanoacetanilides proceeded efficiently under mild conditions to give 4-hydroxy-3-trifluoroacetylquinolin-2(1H)-ones in good yields. Isolation and direct observation of the reaction intermediates revealed that alpha-trifluoroacetylation resulted in the shortening of C N bonds and that the electron density of CN groups was high. A plausible reaction mechanism based on the results is also described.

  DOI：

  10.1021/jo100220m

文献信息

• α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones
  作者：Yusuke Kobayashi、Terue Nakatani、Rie Tanaka、Mari Okada、Eri Torii、Takashi Harayama、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2011.03.040

  日期：2011.5

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.
• COPPOLA G. M.; HARDTMANN G. E., J. HETEROCYCL. CHEM., 1979, 16, NO 8, 1605-1610
  作者：COPPOLA G. M.、 HARDTMANN G. E.

  DOI：——

  日期：——