(Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride | 145038-67-1

• 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
• 英文名称: (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride
• 英文别名: 6-tert-butoxycarbonyl-(Z)-5-propylidene-(7aS)-3a,6-diazaperhydroindane-4,7-dione；tert-butyl (3Z,8aS)-1,4-dioxo-3-propylidene-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-2-carboxylate
• CAS: 145038-67-1
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: JIZZFOJQIIEWSA-QBQSQJOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride 在 盐酸 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 192.0h， 生成 (+)-(1R,2S)-allocoronamic acid
  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：

  (8αS)-(1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-yl)-phosphonic acid dimethyl ester 在 4-二甲氨基吡啶 、 TEA 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride
  参考文献：
  名称：

  Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid

  摘要：

  The asymmetric synthesis of (+)-(1R,2S)-allocoronamic acid is reported. Diazomethane addition to (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photolysis and acid hydrolysis of the resulting spirocyclopropane, into (+)-(1R,2S)-1-amino-2-ethyl-cyclopropanecarboxylic acid.

  DOI：

  10.1016/s0040-4039(00)61159-0

文献信息

• 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.
• Enantioselective synthesis of (+)-(1R,2S)-allocoronamic acid
  作者：Carmen Alcaraz、Angela Herrero、José L. Marco、Eldiberto Fernández-Alvarez、Manuel Bernabé

  DOI：10.1016/s0040-4039(00)61159-0

  日期：1992.9

  The asymmetric synthesis of (+)-(1R,2S)-allocoronamic acid is reported. Diazomethane addition to (Z)-N-(tert-butoxycarbonyl)ethyldehydroalanyl-L-prolin-anhydride, easily prepared from (Z)-2-phenyl-4-propylidene-5(4H)-oxazolone and L-proline, gave in high diastereomeric excess the corresponding spiropyrazoline, which was transformed, on photolysis and acid hydrolysis of the resulting spirocyclopropane, into (+)-(1R,2S)-1-amino-2-ethyl-cyclopropanecarboxylic acid.