(7aS)-3a,6-diazaperhydroindane-4,7-dione-5-spiro-1'-<(1'R,2'R)-2'-phenylcyclopropane> | 161793-88-0

• 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: (7aS)-3a,6-diazaperhydroindane-4,7-dione-5-spiro-1'-<(1'R,2'R)-2'-phenylcyclopropane>
• CAS: 161793-88-0
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: BMAFRWLQQDCNRC-TYNCELHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  triethyloxonium fluoroborate 、 (7aS)-3a,6-diazaperhydroindane-4,7-dione-5-spiro-1'-<(1'R,2'R)-2'-phenylcyclopropane> 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(7aS)-3a,6-diaza-7-ethoxy-3a,4,5,7a-tetrahydroindane-4-one-5-spiro-1'-<(1'R,2'R)-2'-phenylcyclopropane>
  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：

  (3Z,8aS)-2-acetyl-3-benzylidene-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione 在 盐酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 10.0h， 生成 (7aS)-3a,6-diazaperhydroindane-4,7-dione-5-spiro-1'-<(1'R,2'R)-2'-phenylcyclopropane>
  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