(3Z,8aS)-(9CI)-3-亚乙基六氢吡咯并[1,2-a]吡嗪-1,4-二酮 | 114604-89-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (3Z,8aS)-(9CI)-3-亚乙基六氢吡咯并[1,2-a]吡嗪-1,4-二酮
• 英文名称: (S,Z)-3-Ethylidenehexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: (3Z,8aS)-3-ethylidene-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 114604-89-6
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: ZNFUNIIHSUSXNE-OUKKNOHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3Z,8aS)-(9CI)-3-亚乙基六氢吡咯并[1,2-a]吡嗪-1,4-二酮 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 168.0h， 生成 6-tert-butoxycarbonyl-(7aS)-3a,6-diazaperhydroindane-4,7-dione-5-spiro-1'-<(1'S,2'S)-2'-methylcyclopropane>
  参考文献：
  名称：

  Asymmetric syntheses of 1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines

  摘要：

  Monochiral alpha-benzamidocinnamic esters of N-methylephedrine or mandelic derivatives and benzylidene or alkylidene diketopiperazines, all obtained from oxazolones, react with diazomethane to give moderate to high diastereomeric excess (d.e) of pyrazoline derivatives which after photolysis and acid hydrolysis of the resulting cyclopropyl compounds, gave (1R,2R)-, (1S,2S)- or (1S,2R)-1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids. The enantiomerically pure dipeptide of the (1R,2R) enantiomer with S-proline was also obtained by selective cleavage of the diketopiperazine moiety. The structure of all compounds has been assessed by NMR studies and by X-ray crystallography analysis of an intermediate spiroderivative.

  DOI：

  10.1016/s0040-4020(01)89550-8
• 作为产物：
  描述：

  L-脯氨酸 在 碳酸氢钠 作用下， 以 叔丁醇 为溶剂， 生成 (3Z,8aS)-(9CI)-3-亚乙基六氢吡咯并[1,2-a]吡嗪-1,4-二酮
  参考文献：
  名称：

  Rational design and synthesis of unsaturated 2,5-dioxopiperazine derivatives as potential protein tyrosine kinase inhibitors

  摘要：

  The first general method for the synthesis of a library of trifunctionalized (Z)-3-alkylidene-2,5-piperazinediones as potential protein tyrosine kinase inhibitors from commercially available amino compounds, alpha-keto acids and aldehydes using a novel cyclization/cleavage strategy on solid support is described. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01599-8

文献信息

• What is the structure of barettin? Novel synthesis of unsaturated diketopiperazines.
  作者：Albrecht Lieberknecht、Helmut Griesser

  DOI：10.1016/s0040-4039(00)96483-9

  日期：1987.1
• LIEBERKNECHT, ALBRECHT;GRIESSER, HELMUT, TETRAHEDRON LETT., 28,(1987) N 37, 4275-4278
  作者：LIEBERKNECHT, ALBRECHT、GRIESSER, HELMUT

  DOI：——

  日期：——
• Asymmetric syntheses of 1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines
  作者：Carmen Alcaraz、Ma Dolores Fernández、Ma Pilar de Frutos、Joseé L. Marco、Manuel Bernabé、Concepción Foces-Foces、Félix H. Cano

  DOI：10.1016/s0040-4020(01)89550-8

  日期：1994.1

  Monochiral alpha-benzamidocinnamic esters of N-methylephedrine or mandelic derivatives and benzylidene or alkylidene diketopiperazines, all obtained from oxazolones, react with diazomethane to give moderate to high diastereomeric excess (d.e) of pyrazoline derivatives which after photolysis and acid hydrolysis of the resulting cyclopropyl compounds, gave (1R,2R)-, (1S,2S)- or (1S,2R)-1-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids. The enantiomerically pure dipeptide of the (1R,2R) enantiomer with S-proline was also obtained by selective cleavage of the diketopiperazine moiety. The structure of all compounds has been assessed by NMR studies and by X-ray crystallography analysis of an intermediate spiroderivative.
• Rational design and synthesis of unsaturated 2,5-dioxopiperazine derivatives as potential protein tyrosine kinase inhibitors
  作者：Wen-Ren Li、Shao-Zheng Peng

  DOI：10.1016/s0040-4039(98)01599-8

  日期：1998.10

  The first general method for the synthesis of a library of trifunctionalized (Z)-3-alkylidene-2,5-piperazinediones as potential protein tyrosine kinase inhibitors from commercially available amino compounds, alpha-keto acids and aldehydes using a novel cyclization/cleavage strategy on solid support is described. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.