1-benzyl-5-chloro-6-methyl-3-phenylpyrazin-2(1H)-one | 180893-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-benzyl-5-chloro-6-methyl-3-phenylpyrazin-2(1H)-one
• 英文别名: 1-benzyl-5-chloro-6-methyl-3-phenylpyrazin-2-one
• CAS: 180893-34-9
• 化学式: C₁₈H₁₅ClN₂O
• 分子量: 310.783
• InChiKey: YMVHTHONTFEDRD-UHFFFAOYSA-N

物化性质

• 沸点：
  441.5±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-chloro-6-methyl-3-phenylpyrazin-2(1H)-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones

  摘要：

  2(1H)-pyrazinones 7, 10 or 12 with in 6-position a 2-propynylaminomethyl or 3-butynylaminomethyl side chain undergo intramolecular Diels-Alder reactions providing cycloadducts which can he isolated or functionalised in some cases. By further thermolysis of these compounds either pyrrolo-[3,4-b]pyridinones 15/16 and/or pyrrolo[3,4-c]pyridines 17/18 or 1.7-naphthyridinones 25 and/or 2,7-naphthyridines 26 can be generated. Loss of either cyanide or isocyanate from the respective adducts is shown to be dependent on their substitution pattern. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00467-x
• 作为产物：
  描述：

  、 苯基三甲氧基硅烷 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以88%的产率得到1-benzyl-5-chloro-6-methyl-3-phenylpyrazin-2(1H)-one
  参考文献：
  名称：

  （杂）芳基硫代酯和硫醚与芳基硅氧烷的钯催化脱硫CC交叉偶联反应

  摘要：

  报道了第一个脱硫的Hiyama型交叉偶联方案，并以取代的5-氯-3-芳基吡嗪酮的合成为例。该方法也已成功地用于其他（杂）芳基硫醚和硫酯的芳基化。

  DOI：

  10.1002/adsc.200800395

文献信息

• Mild Room-Temperature Palladium-Catalyzed C3-Arylation of 2(1<i>H</i>)-Pyrazinones via a Desulfitative Kumada-Type Cross-Coupling Reaction
  作者：Vaibhav P. Mehta、Sachin G. Modha、Erik Van der Eycken

  DOI：10.1021/jo901327y

  日期：2009.9.4

  An efficient desulfitative Kumada-type cross-coupling protocol is reported for the C3-arylation of 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones. The method has also been successfully extended to the arylation of some (hetero)aryl thioethers and thioesters.

  一个有效的脱硫Kumada型交叉耦合协议已报告为5-氯-3-（苯基硫烷基）吡嗪-2（1 H）-ones的C3-芳基化。该方法也已成功地扩展到某些（杂）芳基硫醚和硫酯的芳基化反应。
• Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position
  作者：Wim M. De Borggraeve、Bie M.P. Verbist、Frederik J.R. Rombouts、Vijaykumar G. Pawar、Wim J. Smets、Laila Kamoune、Jo Alen、Erik V. Van der Eycken、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/j.tet.2004.09.054

  日期：2004.12

  In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external beta-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
  作者：Kris J. Buysens、Didier M. Vandenberghe、Georges J. Hoornaert

  DOI：10.1016/0040-4020(96)00467-x

  日期：1996.7

  2(1H)-pyrazinones 7, 10 or 12 with in 6-position a 2-propynylaminomethyl or 3-butynylaminomethyl side chain undergo intramolecular Diels-Alder reactions providing cycloadducts which can he isolated or functionalised in some cases. By further thermolysis of these compounds either pyrrolo-[3,4-b]pyridinones 15/16 and/or pyrrolo[3,4-c]pyridines 17/18 or 1.7-naphthyridinones 25 and/or 2,7-naphthyridines 26 can be generated. Loss of either cyanide or isocyanate from the respective adducts is shown to be dependent on their substitution pattern. Copyright (C) 1996 Elsevier Science Ltd
• Palladium-Catalyzed Desulfitative CC Cross-Coupling Reaction of (Hetero)Aryl Thioesters and Thioethers with Arylsiloxanes
  作者：Vaibhav Pravinchandra Mehta、Anuj Sharma、Erik Van der Eycken

  DOI：10.1002/adsc.200800395

  日期：2008.10.6

  The first desulfitative Hiyama-type cross-coupling protocol is reported and exemplified by the synthesis of substituted 5-chloro-3-arylpyrazinones. The method has also been successfully applied for the arylation of other (hetero)aryl thioethers and thioesters.

  报道了第一个脱硫的Hiyama型交叉偶联方案，并以取代的5-氯-3-芳基吡嗪酮的合成为例。该方法也已成功地用于其他（杂）芳基硫醚和硫酯的芳基化。