4-trifluoroacetyl-3-(4-methoxybenzyl)-2-phenyl-1,3-oxazolium-5-olate | 1253394-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-trifluoroacetyl-3-(4-methoxybenzyl)-2-phenyl-1,3-oxazolium-5-olate
• CAS: 1253394-10-3
• 化学式: C₁₉H₁₄F₃NO₄
• 分子量: 377.32
• InChiKey: QNVZFGZPXVUOMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.38
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-trifluoroacetyl-3-(4-methoxybenzyl)-2-phenyl-1,3-oxazolium-5-olate 、 甲基三苯基溴化膦 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以87%的产率得到4-trifluoromethyl-1-(4-methoxybenzyl)-2-phenyl-1H-pyrrole
  参考文献：
  名称：

  New Synthesis of 3-Trifluoromethylpyrroles by Condensation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phosphorus Ylides

  摘要：

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give beta-trifluoromethylpyrroles (2) in good yields. The novel ring transformations of 1 into 2 occur via an initial attack of the ylide anions on the C-2 position of the ring.

  DOI：

  10.1021/ol1018689
• 作为产物：
  描述：

  N-benzoyl-N-(4-methoxyphenylmethyl)glycine 、 三氟乙酸酐 以 乙酸乙酯 为溶剂， 以75%的产率得到4-trifluoroacetyl-3-(4-methoxybenzyl)-2-phenyl-1,3-oxazolium-5-olate
  参考文献：
  名称：

  New Synthesis of 3-Trifluoromethylpyrroles by Condensation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phosphorus Ylides

  摘要：

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give beta-trifluoromethylpyrroles (2) in good yields. The novel ring transformations of 1 into 2 occur via an initial attack of the ylide anions on the C-2 position of the ring.

  DOI：

  10.1021/ol1018689

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。
• The use of sulfur ylides in the synthesis of 3-alkyl(aryl)thio-4-trifluoromethylpyrroles from mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates
  作者：Ryosuke Saijo、Masami Kawase

  DOI：10.1016/j.tetlet.2012.03.130

  日期：2012.5

  In this report, we describe a new method for the synthesis of densely functionalized pyrroles. Reaction of mesoionic 1,3-oxazolium-5-olates with various S-ylides proceeds via nucleophilic addition followed by opening of the oxazole ring and subsequent cyclization to multisubstituted pyrroles bearing both a trifluoromethyl and alkyl(aryl)thio group at 3- and 4-positions.

  在这份报告中，我们描述了一种合成高密度官能化吡咯的新方法。通过亲核加成反应，使中离子1,3-恶唑基5-油酸酯与各种S-基化物反应，然后打开恶唑环，随后环化成在3-和4位同时带有三氟甲基和烷基（芳基）硫基的多取代吡咯-位置。
• 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.