2-amino-1-(4-methoxybenzyliden)amino-4-phenylimidazole | 185422-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-amino-1-(4-methoxybenzyliden)amino-4-phenylimidazole
• 英文别名: 1-[(4-Methoxyphenyl)methylideneamino]-4-phenylimidazol-2-amine
• CAS: 185422-34-8
• 化学式: C₁₇H₁₆N₄O
• mdl: MFCD01067620
• 分子量: 292.34
• InChiKey: KUECPEXHYGBZEI-UHFFFAOYSA-N

物化性质

• 沸点：
  541.3±52.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 2-amino-1-(4-methoxybenzyliden)amino-4-phenylimidazole 以 苯 为溶剂， 反应 0.17h， 以22%的产率得到
  参考文献：
  名称：

  Synthesis of Nitrogen-Containing Heterocycles 12. Reactions of 2-Amino-1-benzylideneamino-1H-imidazoles with Dimethyl Acetylenedicarboxylate

  摘要：

  2-Amino-4-aryl-l-benzylideneamino-IH-imidazoles (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in benzene to give dimethyl 2-amino-1-benzylidene-amino-1H-pyrrole-3,4-dicarboxylates (3), benzonitriles (4) and dimethyl 1-(2-amino-1-benzylideneamino-4-aryl-1H-imidazole-5-yl)fumarates (5) in moderate to high yields. Compounds 3 and 4 were considered as the reaction products of the intermediary Diels-Alder adducts, dimethyl 1-amino-3-aryl-7-benzylideneamino-2,7-diazabicylo[2.2.1]hepta-2,5-diene-5,6-dicarboxylates (2), which were not isolated and decomposed in a retro Diels-Alder reaction. The products 5 resulted from a Michael conjugate addition reaction of 1 to DMAD.

  DOI：

  10.3987/com-08-11558
• 作为产物：
  描述：

  (E)-(4-methoxyphenyl)-1,1-diamino-2,3-diazabuta-1,3-diene 、 2-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以56%的产率得到2-amino-1-(4-methoxybenzyliden)amino-4-phenylimidazole
  参考文献：
  名称：

  取代的2-氨基-1-芳基氨基咪唑和1-芳基氨基咪唑并[1,2-a]咪唑的合成

  摘要：

  DOI：

  10.1007/bf01164708

文献信息

• Synthesis of dihydro derivatives of 2-amino-4,5,7-triarylimidazo[1,5-b]pyridazine
  作者：N. N. Kolos、V. D. Orlov、B. V. Paponov、O. V. Shishkin

  DOI：10.1007/bf02323380

  日期：1999.10
• Cascade cyclization of 1,2-diamino-4-phenylimidazole with aromatic aldehydes and cyclohexanediones
  作者：V. V. Lipson、N. V. Svetlichnaya、M. G. Shirobokov、V. I. Musatov、O. V. Shishkin、S. V. Shishkina

  DOI：10.1134/s1070428012020182

  日期：2012.2

  The three-component condensation of 1,2-diamino-4-phenylimidazole with aromatic aldehydes and 1,3-cyclohexanediones occurred regioselectively and afforded 3-amino-1-phenyl-10-aryl-7,8-dihydroimidazo[1,5-b] cinnolin-9(5H,6H,10H)-ones.
• Synthesis of substituted 2-amino-1-arylidenaminoimidazoles and 1-arylidenaminoimidazo[1,2-a]imidazoles
  作者：M. Z. Krimer、F. Z. Makaev、E. P. Styngach、A. G. Koretskii、S. I. Pogrebnoi、A. I. Kochug

  DOI：10.1007/bf01164708

  日期：1996.9
• Synthesis of Nitrogen-Containing Heterocycles 12. Reactions of 2-Amino-1-benzylideneamino-1H-imidazoles with Dimethyl Acetylenedicarboxylate
  作者：Yoshiko Miyamoto

  DOI：10.3987/com-08-11558

  日期：——

  2-Amino-4-aryl-l-benzylideneamino-IH-imidazoles (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in benzene to give dimethyl 2-amino-1-benzylidene-amino-1H-pyrrole-3,4-dicarboxylates (3), benzonitriles (4) and dimethyl 1-(2-amino-1-benzylideneamino-4-aryl-1H-imidazole-5-yl)fumarates (5) in moderate to high yields. Compounds 3 and 4 were considered as the reaction products of the intermediary Diels-Alder adducts, dimethyl 1-amino-3-aryl-7-benzylideneamino-2,7-diazabicylo[2.2.1]hepta-2,5-diene-5,6-dicarboxylates (2), which were not isolated and decomposed in a retro Diels-Alder reaction. The products 5 resulted from a Michael conjugate addition reaction of 1 to DMAD.