1-methyl-5-((4-methylphenyl)sulfonyl)-6-phenylpyrazin-2(1H)-one | 1448021-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-5-((4-methylphenyl)sulfonyl)-6-phenylpyrazin-2(1H)-one
• 英文别名: 1-Methyl-5-(4-methylphenyl)sulfonyl-6-phenylpyrazin-2-one；1-methyl-5-(4-methylphenyl)sulfonyl-6-phenylpyrazin-2-one
• CAS: 1448021-95-1
• 化学式: C₁₈H₁₆N₂O₃S
• 分子量: 340.403
• InChiKey: PGLVRGNQIBHPCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对甲基苯磺酰甲基异腈 、 1-methyl-5-((4-methylphenyl)sulfonyl)-6-phenylpyrazin-2(1H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以94%的产率得到7-methyl-5-((4-methylphenyl)sulfonyl)-6-phenylimidazo[1,5-a]pyrazin-8(7H)-one
  参考文献：
  名称：

  Facile Synthesis of Imidazo[1,5-a]pyrazin-8(7H)-ones from Mesoionic 1,3-Oxazolium-5-olates via a Multistep One-Pot Transformation

  摘要：

  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.

  DOI：

  10.3987/com-16-13551
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 4-trifluoroacetyl-3-methyl-2-phenyl-1,3-oxazolium-5-olate 在 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72%的产率得到1-methyl-5-((4-methylphenyl)sulfonyl)-6-phenylpyrazin-2(1H)-one
  参考文献：
  名称：

  Novel ring transformation of mesoionic oxazoles into 2(1H)-pyrazinones by the reaction with TosMIC

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.06.018

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。
• 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.