4-trif luoroacetyl-2-(4-methoxyphenyl)-3-methyl-1,3-oxazolium-5-olate | 203627-30-9

• 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-trif luoroacetyl-2-(4-methoxyphenyl)-3-methyl-1,3-oxazolium-5-olate
• 英文别名: (1Z)-2,2,2-trifluoro-1-[2-(4-methoxyphenyl)-3-methyl-5-oxo-1,3-oxazol-3-ium-4-ylidene]ethanolate
• CAS: 203627-30-9
• 化学式: C₁₃H₁₀F₃NO₄
• 分子量: 301.222
• InChiKey: PZUOASHUWKAHBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-trif luoroacetyl-2-(4-methoxyphenyl)-3-methyl-1,3-oxazolium-5-olate 在 吡啶 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 N-(3-benzoyloxy-5-trifluoromethyl-1-phenyl-1H-pyrazol-4-yl)-N-methylbenzamide
  参考文献：
  名称：

  中离子型4-三氟乙酰基-1,3-恶唑鎓5-油酸酯与苯肼的区域选择性反应：三氟甲基取代的吡唑和1,2,4-三嗪衍生物的合成

  摘要：

  通过苯肼的区域选择性攻击，有选择地获得了6-三氟甲基-1,2,4-三嗪（2），3-三氟甲基-5-吡唑啉酮（3）或5-三氟甲基-3-羟基吡唑（4）。取决于反应溶剂的性质和温度，中离子的4-三氟乙酰基-1,3-恶唑鎓5-酸酯（1）。

  DOI：

  10.1016/s0040-4039(97)10712-2
• 作为产物：
  描述：

  三氟甲磺酸酐 、 N-(4-甲氧基苯甲酰基)-N-甲基甘氨酸 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到4-trif luoroacetyl-2-(4-methoxyphenyl)-3-methyl-1,3-oxazolium-5-olate
  参考文献：
  名称：

  Heterocyclization of 4-Trifluoroacetyl-1,3-oxazolium-5-olates with 1,4-Bis-nucleophiles

  摘要：

  Reactions of aromatic 1,4-bis-nucleophiles such as o-phenylenediamine and o-aminothiophenol, with mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) gave regiospecifically seven member trifluoromethylated heterocycles such as 1,5-benzodiazepines (3) and 1,5-benzothiazepines (4). The reaction with o-aminophenol afforded non-cyclized products (5). The structures of 3, 4, and 5 were established by X-Ray diffraction analysis.

  DOI：

  10.3987/com-01-9325

文献信息

• A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1<i>H</i>)-Pyrazinones of Biological Interest
  作者：Ryosuke Saijo、Hiroshi Sekiya、Eiji Tamai、Ken-ichi Kurihara、Jun Maki、Hiroshi Sakagami、Masami Kawase

  DOI：10.1248/cpb.c16-00830

  日期：——

  In this report, we describe a new method for the synthesis of densely functionalized 2(1H)-pyrazinones. Treatment of mesoionic 1,3-oxazolium-5-olates with carbanions derived from activated methylene isocyanides (p-toluenesulfonylmethyl isocyanide (TosMIC) and ethyl isocyanoacetate) causes a novel ring transformation affording 2(1H)-pyrazinones in moderate to high yields. The cytotoxicity and antibacterial

  在这份报告中，我们描述了一种新的合成功能密集的2（1H）-吡嗪酮的方法。用衍生自活化亚甲基异氰酸酯（对甲苯磺酰基甲基异氰酸酯（TosMIC）和异氰基乙酸乙酯）的碳负离子处理中离子1,3-恶唑鎓5-酸酯，会引起新的环转化，从而以中等至高收率提供2（1H）-吡嗪酮。研究了一些所得产物的细胞毒性和抗菌活性，并且某些产物表现出肿瘤特异性的细胞毒性。
• Synthesis of Trifluoromethyl-Substituted Pyrazoles and 1,2,4-Triazines by Ring Transformation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phenylhydrazine
  作者：Masami Kawase、Hiromi Koiwai

  DOI：10.1248/cpb.56.433

  日期：——

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates 1 were easily prepared by the cyclodehydration reaction of N-acyl-N-alkyl-alpha-amino acids with trifluoroacetic anhydride. Due to the presence of the trifluoromethyl ketone and the mesoionic five-membered oxazole, there are three reaction sites to be attacked by the nucleophiles at C-2, C-5 and the trifluoroacetyl group in 1. Based on this model,

  通过N-酰基-N-烷基-α-氨基酸与三氟乙酸酐的环脱水反应，可以容易地制备介电的4-三氟乙酰基-1,3-恶唑鎓-5-酸酯。由于三氟甲基酮和中性离子五元恶唑的存在，亲核试剂在C-1，C-5和三氟乙酰基上存在三个反应位点。基于该模型，三种模式发现苯肼的区域选择性攻击提供了三种不同的产物，分别以良好的产率提供了6-三氟甲基-1,2,4-三嗪3、3-三氟甲基-5-吡唑酮5和5-三氟甲基-3-羟基吡唑4。 ，取决于溶剂的性质和反应温度。
• Facile Synthesis of Imidazo[1,5-a]pyrazin-8(7H)-ones from Mesoionic 1,3-Oxazolium-5-olates via a Multistep One-Pot Transformation
  作者：Masami Kawase、Ryosuke Saijo、Hidemitsu Uno

  DOI：10.3987/com-16-13551

  日期：——

  A novel one-pot conversion of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates into imidazo[1,5-a]pyrazin-8(7.H)-ones by the reaction with TosMIC is described. The structure of the product was determined by single-crystal X-ray analysis.
• Novel ring transformation of mesoionic oxazoles into 2(1H)-pyrazinones by the reaction with TosMIC
  作者：Ryosuke Saijo、Ken-ichi Kurihara、Kazuki Akira、Hidemitsu Uno、Masami Kawase

  DOI：10.1016/j.tetlet.2013.06.018

  日期：2013.8

  Treatment of mesoionic 1,3-oxazolium-5-olates with TosMIC in the presence of a base causes a novel ring transformation affording 2(1H)-pyrazinones in moderate yields. The origin of C-2 carbonyl oxygen in the product was elucidated to be molecular oxygen, based on O-18-labeling experiments.[GRAPHICS].(C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• Synthesis of Functionalized Pyrrolidines from Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates and Aminomalonate
  作者：Masami Kawase、Hiroshi Miyamae、Setsuo Saito

  DOI：10.3987/com-98-s(h)46

  日期：——

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) undergo tandem addition of aminomalonate to afford 3-amido-4-trifluoromethylpyrrolidin-2-ones (2) in moderate yields.