3-(4-Amino-6-phenyl-[1,3,5]triazin-2-yl)-propionic acid methyl ester | 130670-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-(4-Amino-6-phenyl-[1,3,5]triazin-2-yl)-propionic acid methyl ester
• 英文别名: Methyl 3-(4-amino-6-phenyl-1,3,5-triazin-2-yl)propanoate
• CAS: 130670-14-3
• 化学式: C₁₃H₁₄N₄O₂
• 分子量: 258.28
• InChiKey: XRFYDLVLNYTMFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  盐酸胍 、 methyl (E)-3-phenyl-2H-azirine-2-acrylate 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 120.0h， 以35%的产率得到3-(4-Amino-6-phenyl-[1,3,5]triazin-2-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Reaction of methyl (E)-2-phenyl-1-azirine-3-acrylates with hydrazines and amidines. Synthetic and mechanistic implications

  摘要：

  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.

  DOI：

  10.1021/jo00001a004

文献信息

• 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：——