(Z)-3-(2-Methyl-2H-benzotriazol-5-ylamino)-acrylic acid methyl ester | 173317-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: (Z)-3-(2-Methyl-2H-benzotriazol-5-ylamino)-acrylic acid methyl ester
• CAS: 173317-12-9
• 化学式: C₁₁H₁₂N₄O₂
• 分子量: 232.242
• InChiKey: OMQZXUMPKHRPTA-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.04
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-Methyl-2H-benzotriazol-5-ylamino)-acrylic acid methyl ester 以 various solvent(s) 为溶剂， 反应 0.33h， 以94%的产率得到9-oxo-2-methyl-2H-triazolo<4,5-f>quinoline
  参考文献：
  名称：

  Reaction of 5-Aminobenzotriazoles with Methyl Propiolate. Formation of Triazolo[4,5-f]quinolines and Related Compounds. Unusual Products in the Michael Addition Reaction of 2-Methyl-2H-5-aminobenzotriazole

  摘要：

  Reaction of 5-aminobenzotriazoles (1b-d) with methyl propiolate gives (Z/E)-3-[1(2)(3)-methyl(benzotriazol-5-yl)]aminomonopropenoates (5b-d) and (E)-3-[1(2)(3)-methyl(benzotriazol-5-yl)]aminobispropenoates (6b-d), while in the case of la addition took place on the nitrogen of the triazole ring to give mixtures of (E)-3-(5-aminobenzotriazol-1(2)(3)-yl)propenoates (2,3,4). Mono- (5b-d) and bis-adducts (6b-d) underwent further reaction which also led to the isolation of triazolo[4,5-f]quinolines, of a triazolo[4,5-f]carbostyril and 1-[benzotriazol-5-yl]-2-pyridones. Formation of these compounds depends on the reaction conditions: the solvent employed and the temperature. Thermal cyclization of Michael adduct (Z/E)-(5c) gave triazoloquinolinone (9c) and the rearranged product (13) in various ratio depending on the concentration of Dowtherm used.

  DOI：

  10.3987/com-95-7145
• 作为产物：
  描述：

  2-methyl-2H-benzotriazol-5-amine 、 丙炔酸甲酯 反应 90.0h， 以33%的产率得到(Z)-3-(2-Methyl-2H-benzotriazol-5-ylamino)-acrylic acid methyl ester
  参考文献：
  名称：

  Reaction of 5-Aminobenzotriazoles with Methyl Propiolate. Formation of Triazolo[4,5-f]quinolines and Related Compounds. Unusual Products in the Michael Addition Reaction of 2-Methyl-2H-5-aminobenzotriazole

  摘要：

  Reaction of 5-aminobenzotriazoles (1b-d) with methyl propiolate gives (Z/E)-3-[1(2)(3)-methyl(benzotriazol-5-yl)]aminomonopropenoates (5b-d) and (E)-3-[1(2)(3)-methyl(benzotriazol-5-yl)]aminobispropenoates (6b-d), while in the case of la addition took place on the nitrogen of the triazole ring to give mixtures of (E)-3-(5-aminobenzotriazol-1(2)(3)-yl)propenoates (2,3,4). Mono- (5b-d) and bis-adducts (6b-d) underwent further reaction which also led to the isolation of triazolo[4,5-f]quinolines, of a triazolo[4,5-f]carbostyril and 1-[benzotriazol-5-yl]-2-pyridones. Formation of these compounds depends on the reaction conditions: the solvent employed and the temperature. Thermal cyclization of Michael adduct (Z/E)-(5c) gave triazoloquinolinone (9c) and the rearranged product (13) in various ratio depending on the concentration of Dowtherm used.

  DOI：

  10.3987/com-95-7145