methyl (E)-3-(2-methyl-3-phenylazirin-2-yl)prop-2-enoate | 130670-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 叠氮烷
• 英文名称: methyl (E)-3-(2-methyl-3-phenylazirin-2-yl)prop-2-enoate
• CAS: 130670-06-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: KUFXJMCPZVTBAL-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(2-methyl-3-phenylazirin-2-yl)prop-2-enoate 以 苯 为溶剂， 反应 54.0h， 生成 (E)-3-((2R,3S)-2-Methoxy-3-methyl-5-oxo-2,4,4-triphenyl-pyrrolidin-3-yl)-acrylic acid methyl ester
  参考文献：
  名称：

  1-丙烯基-3-甲基丙烯酸的亚甲基酯及其衍生物与二苯乙烯酮的反应。通往5-吡咯啉-2-酮的便捷途径

  摘要：

  1-叠氮基1a-d与二苯乙烯酮反应，可得到1：1的加合物，显示为5-吡咯啉-2-酮3a-d。描述了3的一些转换。

  DOI：

  10.1016/s0040-4020(97)00388-8

文献信息

• Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-<i>Z</i> Mode:  Convenient Route to 2-Aza-1,3-dienes
  作者：Marcia T. Barroso、Albert Kascheres

  DOI：10.1021/jo980198u

  日期：1999.1.1

  Reaction of 1-azirine-3-methylacrylates 1a,b with imidazoles and pyrazoles under mild conditions results in the formation of 2-aza-1,3-dienes 2a-g containing a potential leaving group at the 1-position. Simple alcohols (methanol and ethanol) react similarly with la,b in the presence of sodium carbonate to afford 2h-j. Utilization of 2 in the hetero Diels-Alder reaction with electron-deficient dienophiles is described.
• Reaction of methyl (E)-2-phenyl-1-azirine-3-acrylates with hydrazines and amidines. Synthetic and mechanistic implications
  作者：Albert Kascheres、Cecilia M. A. Oliveira、Mariangela B. M. De Azevedo、Cintia M. S. Nobre

  DOI：10.1021/jo00001a004

  日期：1991.1

  1-Azirines 2a-b react with hydrazine in methanol to produce hexahydropyrrolo[3,2-c]pyrazol-5-ones 3a-b. The process is suggested to involve intramolecular interception of an unstable 4-aminopyrazoline intermediate resulting from C=N bond cleavage. Reaction of 2a with phenylhydrazine similarly affords 3c. In dimethyl sulfoxide, on the other hand, formamidine, guanidine, and hydrazine afford imidazole 4, pyrimidines 5a-b, amino-s-triazine 6, or triazole 9 as a consequence of C-C bond cleavage in aziridine intermediate 8. The intermediacy of tautomers is proposed to account for the diversity of products in this case.
• KASCHERES, ALBERT;OLIVEIRA, CECILIA M. A.;DE, AZEVEDO MARIANGELA B. M.;NO+, J. ORG. CHEM., 56,(1991) N, C. 7-9
  作者：KASCHERES, ALBERT、OLIVEIRA, CECILIA M. A.、DE, AZEVEDO MARIANGELA B. M.、NO+

  DOI：——

  日期：——
• Reaction of a 1-azirine-3-methylacrylate and derivatives with diphenylketene. A convenient route to 5-pyrrolin-2-ones
  作者：Albert Kascheres、José Nunes、Fernando Brandão

  DOI：10.1016/s0040-4020(97)00388-8

  日期：1997.5

  Reaction of 1-azirines 1a-d with diphenylketene afforded 1:1 adducts that were shown to be 5-pyrrolin-2-ones 3a-d. Some transformations of 3 are described.

  1-叠氮基1a-d与二苯乙烯酮反应，可得到1：1的加合物，显示为5-吡咯啉-2-酮3a-d。描述了3的一些转换。