2(1H)-吡嗪酮,3,5-二氯-6-苯基-1-(苯基甲基)- | 138610-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2(1H)-吡嗪酮,3,5-二氯-6-苯基-1-(苯基甲基)-
• 英文名称: 1-benzyl-3,5-dichloro-6-phenyl-2(1H)-pyrazinone
• 英文别名: 2(1H)-Pyrazinone, 3,5-dichloro-6-phenyl-1-(phenylmethyl)-；1-benzyl-3,5-dichloro-6-phenylpyrazin-2-one
• CAS: 138610-71-6
• 化学式: C₁₇H₁₂Cl₂N₂O
• 分子量: 331.201
• InChiKey: BITMPVLDUYOJFU-UHFFFAOYSA-N

物化性质

• 沸点：
  462.6±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2(1H)-吡嗪酮,3,5-二氯-6-苯基-1-(苯基甲基)- 在 四(三苯基膦)钯 sodium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到1-benzyl-5-chloro-6-phenyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Stereoselective transformation of pyrazinones into substituted analogues of cis-5-amino-6-oxo-2-piperidinemethanol and cis-5-amino-2-piperidinemethanol

  摘要：

  Various analogues of cis-5-amino-6-oxo-2-piperidinemethanol and c-is-5-amino-2-piperidinemethanol have been prepared via Diels-Alder reaction of substituted pyrazinones with ethene followed by acid methanolysis of the bridged lactam adducts. Further reduction of the resulting methyl 2-piperidinecarboxylate ester compounds led to the corresponding 2-piperidinemethanol products that were converted into potential SP antagonists. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00741-5
• 作为产物：
  描述：

  苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺盐酸盐 作用下， 以 氯苯 为溶剂， 生成 2(1H)-吡嗪酮,3,5-二氯-6-苯基-1-(苯基甲基)-
  参考文献：
  名称：

  Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.09.054

文献信息

• Intramolecular Diels-Alder reactions of 2(1H)-pyrazinones: Synthesis of new Furo/Pyrano-pyridinones and -pyridines
  作者：Kris J. Buysens、Didier M. Vandenberghe、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1016/0040-4020(95)00802-f

  日期：1995.11

  4-alkynyloxy side chain and 2(1H)-pyrazinones 9–10 carrying the corresponding 2- or 3-alkynyloxy(m)ethyl substituent are shown to undergo intramolecular Diels-Alder reaction. The formation of either fused pyridinones 13, 16, 20, 22 or 24 and/or pyridines 14, 17, 19 or 25 depends on the substitution pattern of the anchored pyrazinone and runs via the loss of either nitrile or isocyanate from the intermediate

  2（1 H）-吡嗪酮2-5，在3-位带有3-或4-炔基氧基侧链，2（1 H）-吡嗪酮9-10带有相应的2-或3-炔基氧基（m）乙基取代基显示出发生分子内Diels-Alder反应。是稠合吡啶酮的形成13，16，20，22或24和/或吡啶14，17，19或25取决于锚定的吡嗪酮和运行的取代模式通过中间体环加合物损失了腈或异氰酸酯。还讨论了氧原子的位置和侧链的长度对反应条件的影响。
• New routes for the synthesis of 3- and 5-substituted 2(1H)-pyrazinones
  作者：Rasha Azzam、Wim De Borggraeve、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/j.tetlet.2004.01.017

  日期：2004.2

  Furthermore, following hydrogenolysis of the 5-chloro substituent and regioselective 5-bromination, this palladium-catalysed cross-coupling approach could be extended to the synthesis of the analogous 5-substituted 2(1H)-pyrazinones.

  通过将Suzuki和Heck反应方法应用于3,5-二氯-2（1 H）-吡嗪酮制备了各种3-（杂）芳基，3-烷基和3-烯基-2（1 H）-吡嗪酮。此外，继5-氯取代基的氢解和区域选择性的5-溴化之后，这种钯催化的交叉偶联方法可以扩展到类似的5-取代的2（1 H）-吡嗪酮的合成。
• Synthesis of α-carbolines and β-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
  作者：Abdellah Tahri、Kris J. Buysens、Erik V. Van der Eycken、Didier M. Vandenberghe、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(98)00802-3

  日期：1998.10

  2(1H)-Pyrazinones bearing a X-(o-C6H4)CC-R moiety (X=NH, NAc) are shown to undergo an intramolecular cycloaddition-elimination reaction on thermolysis in refluxing bromobenzene yielding α-carbolines or β-carbolinones. The product distribution depends strongly on the substitution pattern of the pyrazinone precursors and the solvent used for thermolysis. A high yield and selective formation of β-carbolinones

  显示带有X-（o -C 6 H 4）CCR部分（X = NH，NAc）的2（1 H）-吡嗪酮在回流过程中发生热分解过程中发生分子内环加成消除反应，从而生成溴代溴苯或β-咔啉酮。产物分布在很大程度上取决于吡嗪酮前体的取代方式和用于热解的溶剂。当在四氢萘中回流加热时，​​可以高收率和选择性形成β-咔啉酮。使用乙酸酐作为溶剂促进了反应，并且使得通过在前述溶剂中热解无法获得的咔啉成为可能。
• Synthesis of Novel Functionalised Symmetric Bi-2(1<i>H</i>)-pyrazinones
  作者：Wim M. De Borggraeve、Prasad Appukkuttan、Rasha Azzam、Wim Dehaen、Frans Compernolle、Erik Van der Eycken、Georges Hoornaert

  DOI：10.1055/s-2005-863747

  日期：——

  A simple and convenient synthesis for functionalised bi-2(1H)-pyrazinones 9, 11a-h starting from 3,5-dichloro-2(1H)-pyrazinones 7, 10a-h is described. The pyrazinone is homo-coupled by means of a Suzuki-type reaction of an in situ generated boronate. The reactions were carried out under conventional heating as well as under microwave irradiation and dramatic improvements in the rates and yields have been observed under the latter conditions.

  本文介绍了一种简单方便的合成方法，即从 3,5-二氯-2(1H)-吡嗪酮 7、10a-h 开始，合成功能化双-2(1H)-吡嗪酮 9、11a-h。吡嗪酮是通过原位生成的硼酸盐的苏木型反应进行均偶合的。反应在常规加热和微波辐照条件下进行，在微波辐照条件下，反应的速率和产率都有显著提高。
• Divergent pathways in the intramolecular diels-alder reaction of 2(1H)-pyrazinones substituted at the 3-position with a phenylalkyne containing side chain
  作者：A. Tahri、W. De Borggraeve、K. Buysens、L. Van Meervelt、F. Compernolle、G.J. Hoornaert

  DOI：10.1016/s0040-4020(99)00913-8

  日期：1999.12

  2(1H)-Pyrazinones bearing an X-(o-C6H4)-CC-R moiety (X = O or NH; R = H, Ph or TMS) at position 3 were subjected to intramolecular Diels-Alder reaction. For the ether compounds (X = O) cycloaddition-elimination occurred readily to produce either benzofuro[2,3-c]pyridin-1(2-H)-ones or benzofuro[2,3-b]pyridines. For the aniline derivatives (X = NH, R = H or TMS) thermolysis in acetic anhydride resulted

  在位置3上带有X-（o -C 6 H 4）-CCR部分（X = O或NH; R = H，Ph或TMS）的2（1 H）-吡嗪酮进行分子内Diels-Alder反应。对于醚类化合物（X = O），很容易发生环加成消除反应，从而生成苯并呋喃[2,3- c ]吡啶-1（2- H）-ones或苯并呋喃[2,3- b]吡啶。对于苯胺衍生物（X = NH，R = H或TMS），在乙酸酐中进行热分解可产生类似的β-咔啉酮和α-咔啉产物分布，但是与先前在回流四氢萘中获得的产物分布不同。该结果由苯胺NH-乙酰化的前体进行的环加成反应解释。然而，具有Ph作为炔属端基（X ＝ NH，R ＝ Ph）的苯胺衍生物通过发散途径反应产生N-（2-氧代吡嗪-3-基）-2-Ph-取代的吲哚。