1-tert-Butyl-5-(dimethylamino-methyleneamino)-1H-imidazole-4-carboxylic acid | 220394-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-tert-Butyl-5-(dimethylamino-methyleneamino)-1H-imidazole-4-carboxylic acid
• CAS: 220394-65-0
• 化学式: C₁₁H₁₈N₄O₂
• 分子量: 238.29
• InChiKey: FPKNIXZTZZBVIQ-AWNIVKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  70.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  氰基磷酸二乙酯 、 1-tert-Butyl-5-(dimethylamino-methyleneamino)-1H-imidazole-4-carboxylic acid 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以62%的产率得到1-t-butyl-5-N-(dimethylaminomethylene) amino imidazole-4-carbonyl cyanide
  参考文献：
  名称：

  摘要：

  1-t-Butyl-5-N-(dimethylaminomethylene)aminoimidazole-4-carbonyl cyanide (BUNDAMIC) is the first acyl cyanide to be synthesized from an imidazole-4-carboxylic acid, diethylphosphorocyanidate, and triethylamine and its structure determined by x-ray crystallography. It crystallizes with four molecules in the monoclinic space group (C) under bar 2/(m) under bar with a = 17.824(2), b = 6.784(2), c = 11.039(2) Angstrom, and beta = 96.17(1)degrees; (R) under bar = 0.036 over 1086 unique x-ray reflections. The cyanocarbonyl group is nearly linear, C-C = N angle 174.4(3)degrees, with dimensions C = N, 1.137(3); C-C, 1.493(3); and C = O, 1.224(3) Angstrom. The imidazole ring, in the mirror plane, has a lengthened C4 = C5 bond of 1.421(3) Angstrom, and there is a short ring-closing approach, H ... O6 = 2.07 Angstrom, between the methyleneamino hydrogen and the carbonyl oxygen.

  DOI：

  10.1023/a:1023200307429
• 作为产物：
  描述：

  1-tert-Butyl-5-(dimethylamino-methyleneamino)-1H-imidazole-4-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以100%的产率得到1-tert-Butyl-5-(dimethylamino-methyleneamino)-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  摘要：

  1-t-Butyl-5-N-(dimethylaminomethylene)aminoimidazole-4-carbonyl cyanide (BUNDAMIC) is the first acyl cyanide to be synthesized from an imidazole-4-carboxylic acid, diethylphosphorocyanidate, and triethylamine and its structure determined by x-ray crystallography. It crystallizes with four molecules in the monoclinic space group (C) under bar 2/(m) under bar with a = 17.824(2), b = 6.784(2), c = 11.039(2) Angstrom, and beta = 96.17(1)degrees; (R) under bar = 0.036 over 1086 unique x-ray reflections. The cyanocarbonyl group is nearly linear, C-C = N angle 174.4(3)degrees, with dimensions C = N, 1.137(3); C-C, 1.493(3); and C = O, 1.224(3) Angstrom. The imidazole ring, in the mirror plane, has a lengthened C4 = C5 bond of 1.421(3) Angstrom, and there is a short ring-closing approach, H ... O6 = 2.07 Angstrom, between the methyleneamino hydrogen and the carbonyl oxygen.

  DOI：

  10.1023/a:1023200307429