5-amino-1-(3,4-dimethoxyphenyl)-4-cyanoimidazole | 155579-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-(3,4-dimethoxyphenyl)-4-cyanoimidazole
• 英文别名: 5-amino-1-(3,4-dimethoxyphenyl)-1H-imidazole-4-carbonitrile；5-amino-1-(3,4-dimethoxyphenyl)imidazole-4-carbonitrile
• CAS: 155579-45-6
• 化学式: C₁₂H₁₂N₄O₂
• 分子量: 244.253
• InChiKey: DYOKRYYJOMOXEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-1-(3,4-dimethoxyphenyl)-4-cyanoimidazole 在 氨 、 乙酸酐 作用下， 以 甲醇 为溶剂， 生成 6-amino-9-(3,4-dimethoxyphenyl)purine
  参考文献：
  名称：

  Synthesis of 9-Aryl-6-aminopurines from 5-Amino-1-aryl-1H-imidazole-4-carbonitriles

  摘要：

  5-Amino-1-aryl-1H-imidazole-4-carbonitriles were converted into 9-aryl-6-aminopurines via imidates formation at treating with CH(OEt)(3) and Ac2O followed by reaction with ammonia.

  DOI：

  10.1023/b:rujo.0000013141.59809.a3
• 作为产物：
  描述：

  N¹-(3,4-dimethoxyphenyl)-N²-(Z)-[2-amino-1,2-dicyanovinyl]formamidine 在 氢氧化钾 作用下， 以89%的产率得到5-amino-1-(3,4-dimethoxyphenyl)-4-cyanoimidazole
  参考文献：
  名称：

  SYNTHESIS OF 5-AMINO-1- ARYL-4-CYANOIMIDAZOLES FROMN-ARYL-N′-(1,2-DICYANOVINYL)- FORMAMIDINES

  摘要：

  The aryl-(Z)-N-[2-amino-1,2-dicyanovinyl]formandine cyclize in the presence of base to give a 1,5-diamino-4-cyanoimidazole or a 1,5-diamino-4-(cyanoformimidoyl)imidazole, depending on the reaction conditions and the nature of the base used to induced cyclization.

  DOI：

  10.1081/scc-100106031

文献信息

• Synthesis of 1-Substituted 5-Aminoimidazole-4-carbaldehydes and 8-Amino-1-(2-fluorobenzyl)imidazo[4’,5’:5,6]pyrido[2,3-<b><i>d</i></b>]pyrimidine
  作者：Brian Booth、Robert Carpenter、Gaby Morlock、Zahid Mahmood、Robin Pritchard

  DOI：10.1055/s-2001-18705

  日期：——

  The syntheses of a number of 1-substituted 5-aminoimidazole-4-carbaldehydes 3, by the reduction of the corresponding 5-amino-4-cyanoimidazole derivatives is reported using LiAlH(OEt)3, prepared in situ from LiAlH4 and ethyl acetate. The compounds of type 1 are useful intermediates for the synthesis of elongated adenine derivatives.

  报道了通过还原相应的5-氨基-4-氰基咪唑衍生物，合成多种1-取代的5-氨基咪唑-4-醛（3），该还原反应使用了由LiAlH4和乙酸乙酯原位制备的LiAlH(OEt)3。类型1的化合物是合成延伸腺苷衍生物的有用中间体。
• Alves, M. Jose; Booth, Brian L; Al-Duaij, Omar Kh., Journal of Chemical Research, Miniprint, 1993, # 10, p. 2701 - 2719
  作者：Alves, M. Jose、Booth, Brian L、Al-Duaij, Omar Kh.、Eastwood, Paul、Nezhat, Lida、et al.

  DOI：——

  日期：——
• SYNTHESIS OF 5-AMINO-1- ARYL-4-CYANOIMIDAZOLES FROM<i>N</i>-ARYL-<i>N</i>′-(1,2-DICYANOVINYL)- FORMAMIDINES
  作者：Asieh Yahya-Zadeh、Brian L. Booth

  DOI：10.1081/scc-100106031

  日期：2001.1

  The aryl-(Z)-N-[2-amino-1,2-dicyanovinyl]formandine cyclize in the presence of base to give a 1,5-diamino-4-cyanoimidazole or a 1,5-diamino-4-(cyanoformimidoyl)imidazole, depending on the reaction conditions and the nature of the base used to induced cyclization.
• Synthesis of 9-Aryl-6-aminopurines from 5-Amino-1-aryl-1H-imidazole-4-carbonitriles
  作者：A. Yahay-Zadeh

  DOI：10.1023/b:rujo.0000013141.59809.a3

  日期：2003.11

  5-Amino-1-aryl-1H-imidazole-4-carbonitriles were converted into 9-aryl-6-aminopurines via imidates formation at treating with CH(OEt)(3) and Ac2O followed by reaction with ammonia.