4-methacryloyl-1-phenyl semicarbazide | 156211-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methacryloyl-1-phenyl semicarbazide
• 英文别名: 4-Methacryloyl-1-phenyl-semicarbazid；N-(anilinocarbamoyl)-2-methylprop-2-enamide
• CAS: 156211-58-4
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: BYXYRVUKJJVCPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.23
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-methacryloyl-1-phenyl semicarbazide 以 间二甲苯 为溶剂， 反应 12.0h， 以76%的产率得到5-Isopropenyl-2-phenyl-1,2-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  Ring Closure Reactions of Adducts of Methacryloyl Isocyanate to Arylhydrazines and Their Related Componds

  摘要：

  Methacryloyl isocyanate (MAI) reacted with arylhydrazines (1) to give semicarbazides (2) in good yields. Treatment of 2 with aqueous potassium hydroxide gave the corresponding 1-aryl-3-hydroxy-1,2,4-triazoles (3), whereas thermal ring closure of 2 afforded isomeric 2,3-dihydro-2-aryl-1,2,4-triazole-3(1H)-ones (4). MAI reacted with benzamidine to give directly 1,3,5-triazine-2(1H)-one (10) by the loss of water. On the other hand, the reaction of MAI with 1,3-diphenylguanidine afforded the 1:1 adduct (11), which on thermal decomposition gave the perhydropyrimidin-6(1H)-one (12) and perhydro-1,3,5-triazine-2,6-dione (13). The pathways for the formation of 4, 12 and 13 are also described.

  DOI：

  10.3987/com-93-6560
• 作为产物：
  描述：

  甲基丙烯酰异氰酸酯 、 苯肼 以 四氢呋喃 为溶剂， 以77%的产率得到4-methacryloyl-1-phenyl semicarbazide
  参考文献：
  名称：

  Ring Closure Reactions of Adducts of Methacryloyl Isocyanate to Arylhydrazines and Their Related Componds

  摘要：

  Methacryloyl isocyanate (MAI) reacted with arylhydrazines (1) to give semicarbazides (2) in good yields. Treatment of 2 with aqueous potassium hydroxide gave the corresponding 1-aryl-3-hydroxy-1,2,4-triazoles (3), whereas thermal ring closure of 2 afforded isomeric 2,3-dihydro-2-aryl-1,2,4-triazole-3(1H)-ones (4). MAI reacted with benzamidine to give directly 1,3,5-triazine-2(1H)-one (10) by the loss of water. On the other hand, the reaction of MAI with 1,3-diphenylguanidine afforded the 1:1 adduct (11), which on thermal decomposition gave the perhydropyrimidin-6(1H)-one (12) and perhydro-1,3,5-triazine-2,6-dione (13). The pathways for the formation of 4, 12 and 13 are also described.

  DOI：

  10.3987/com-93-6560

文献信息

• Lieser; Kemmner, Chemische Berichte, 1951, vol. 84, p. 4,11
  作者：Lieser、Kemmner

  DOI：——

  日期：——