2,2,5,5-tetracyano-trans-3,6-bis(4-carbomethoxyphenyl)piperazine | 131195-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2,2,5,5-tetracyano-trans-3,6-bis(4-carbomethoxyphenyl)piperazine
• 英文别名: methyl 4-[(2R,5S)-3,3,6,6-tetracyano-5-(4-methoxycarbonylphenyl)piperazin-2-yl]benzoate
• CAS: 131195-38-5
• 化学式: C₂₄H₁₈N₆O₄
• 分子量: 454.445
• InChiKey: KHMUCERYPIBBJR-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  对苯二磺酸氨基丙二酰丁氰 、 对甲酰基苯甲酸甲酯 、 甲醇 以32%的产率得到
  参考文献：
  名称：

  FREEMAN, FILLMORE;KIM, DARRICK S. H. L., J. ORG. CHEM., 56,(1991) N, C. 657-663

  摘要：

  DOI：

文献信息

• Reaction of aminopropanedinitrile 4-methylbenzenesulfonate [aminomalononitrile p-toluenesulfonate (tosylate)] with aromatic aldehydes
  作者：Fillmore Freeman、Darrick S. H. L. Kim

  DOI：10.1021/jo00002a031

  日期：1991.1

  Aminopropanedinitrile 4-methylbenzenesulfonate (ammoniopropanedinitrile p-toluenesulfonate, aminomalononitrile p-toluenesulfonate (tosylate), 1) reacts with aromatic aldehydes in methanolic sodium ethanoate to give diastereoselectively (E,E)-4-amino-1-aryl-3-cyano-4-methoxy-2-aza-1,3-butadienes (3) and trans-3,6-diaryl-2,2,5,5-tetracyanopiperazines (4). The product distribution (3:4) depends on the ratio of reactants and the structures of the substrates. Electron-releasing groups on the 4-position of the phenyl ring favor piperazine (4) formation (method B.) The formation of piperazines (4) may involve synthetically useful N-protonated aryl-and cyano-stabilized azomethine ylide (prototropic 1,3-dipoles) intermediates which could have resulted from an imine-azomethine ylide tautomerism of prior formed 1-aryl-3,3-dicyano-2-aza-1-propenes. 1,3-Dipolar cycloaddition [4 + 2] reactions of the highly reactive azomethine ylides with dimethyl 1,2-ethynedicarboxylate (DMAD) give 3,4-dicarbomethoxy-2-cyano-5-aryl-3-pyrrolines, which undergo facile dehydrocyanation to 3,4-dicarbomethoxy-2-cyano-5-arylpyrroles. The possible intermediacy of ketenimines and of aryl- and cyano-stabilized 2-azaallyl anionic intermediates in equilibrium with azomethine ylides is also considered.