2-(3-bromophenyl)-5,7-dimethyl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-1,1-dicarbonitrile | 1207614-75-2

• 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: 2-(3-bromophenyl)-5,7-dimethyl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-1,1-dicarbonitrile
• 英文别名: 1-(3-Bromophenyl)-5,7-dimethyl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-2,2-dicarbonitrile
• CAS: 1207614-75-2
• 化学式: C₁₆H₁₁BrN₄O₃
• 分子量: 387.192
• InChiKey: XBEOJRLIWVVFGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-bromophenyl)-5,7-dimethyl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-1,1-dicarbonitrile 以 二甲基亚砜 为溶剂， 反应 0.5h， 以62%的产率得到
  参考文献：
  名称：

  Stereoselective synthesis of medicinally relevant furo[2,3-d]pyrimidine framework by thermal rearrangement of spirocyclic barbiturates

  摘要：

  在100°C下，二甲基亚砜中替代螺环巴比妥酸盐的热引发转化导致药用相关的呋喃[2,3-d]嘧啶以50-75%的产率立体选择性地形成。

  DOI：

  10.1039/c5ra19169f
• 作为产物：
  描述：

  间溴苯甲醛 在 溴 、 sodium ethanolate 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 2-(3-bromophenyl)-5,7-dimethyl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-1,1-dicarbonitrile
  参考文献：
  名称：

  Electrocatalytic and chemical methods in MHIRC reactions: the first example of the multicomponent assembly of medicinally relevant spirocyclopropylbarbiturates from three different molecules

  摘要：

  Electrolysis of aldehydes, barbituric acids, and malononitrile in alcohol in an undivided cell in the presence of sodium bromide results in efficient MHIRC formation of the corresponding spirocyclopropylbarbiturates in 50-65% substance yield. The electrocatalytic reaction smoothly proceeds under neutral and mild conditions with aromatic aldehydes bearing both electron-donating and electron-withdrawing groups. The implication of electrocatalysis in MHIRC reaction is an efficient approach to medicinally relevant spirocyclopropylbarbiturates avoiding the inconvenient direct use of molecular halogen or halogenated substrates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.029

文献信息

• Pyridinium bromide as a mediator in electrochemical reactions: the preparation of cyclopropane-1,1-dicarbonitriles
  作者：Anatoly N. Vereshchagin、Evgeniya O. Dorofeeva、Michail N. Elinson、Mikhail P. Egorov

  DOI：10.24820/ark.5550190.p011.041

  日期：——

  Pyridinium bromide has been tested as a new mediator for electrochemical transformations in methanol and acetonitrile. An efficient protocol for the synthesis of cyclopropanes via the electrochemical transformations of alkylidenemalononitriles and C-H acids (malononitrile, malonic ester, N,N-dimethylbarbituric acid, pyrazolin-5-ones) has been developed. The chemistry proceeds in a simple undivided

  溴化吡啶作为甲醇和乙腈中电化学转化的新介质已经过测试。已开发出一种通过亚烷基丙二腈和 CH 酸（丙二腈、丙二酸酯、N,N-二甲基巴比妥酸、吡唑啉-5-酮）的电化学转化合成环丙烷的有效方案。该化学反应在恒流条件下在一个简单的未分隔电池中进行，使用亚化学计量的 PyHBr，它既用作氧化还原催化剂又用作支持电解质；以这种方式不需要额外的导电盐。
• The first example of the cascade assembly of a spirocyclopropane structure: direct transformation of benzylidenemalononitriles and N,N′-dialkylbarbituric acids into substituted 2-aryl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-1,1-dicarbonitriles
  作者：Michail N. Elinson、Anatolii N. Vereshchagin、Nikita O. Stepanov、Tatiana A. Zaimovskaya、Valentina M. Merkulova、Gennady I. Nikishin

  DOI：10.1016/j.tetlet.2009.11.065

  日期：2010.1

  The direct formation of substituted 2-aryl-4,6,8-trioxo-5,7-diazaspiro[2.5]octane-1,1-dicarbonitriles in 75-95% yields from benzylidenemalononitriles and N,N'-dialkylbarbituric acids is described. (C) 2009 Elsevier Ltd. All rights reserved.