(9ci)-4-氨基-1-甲基-1H-咪唑-2-羧酸 | 263710-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-4-氨基-1-甲基-1H-咪唑-2-羧酸
• 英文名称: 4-amino-1-methyl-1H-imidazole-2-carboxylic acid
• 英文别名: 4-amino-1-methyl-1H-imidazol-2-carboxylic acid；4-amino-1-methaneyl-2-carboxy-imidazole；4-amino-1-methyl-2-carboxy-imidazole；amino-1-methyl-2-carboxy-imidazole；4-Amino-1-methylimidazole-2-carboxylic acid
• CAS: 263710-28-7
• 化学式: C₅H₇N₃O₂
• mdl: MFCD18808541
• 分子量: 141.129
• InChiKey: PPQDQYBXCYQCNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲乙酐 、 (9ci)-4-氨基-1-甲基-1H-咪唑-2-羧酸 以 四氢呋喃 为溶剂， 以331 mg的产率得到4-甲酰胺基-1-甲基咪唑-2-羧酸
  参考文献：
  名称：

  N‐Formamido‐Containing Mono‐ and Diheterocyclic Pyrrole‐and Imidazole‐2‐carboxylic Acids as Building Blocks for Polyamide Synthesis

  摘要：

  Four N-formamido-containing mono-and diheterocyclic pyrrole- and imidazole-2-containing acids 1-4 were synthesized as intermediates for the preparation of polyamide molecules. The N-formamido-moiety forces the compounds to bind strongly as a stacked dimer, and in a staggered fashion, at specific sequences in the minor-groove of DNA. The acid moiety at the C-terminus of compounds enables these molecules to be coupled to amine-containing intermediates to form the amide linkages of the target polyamide. This convergent approach increases the synthetic diversity in polyamide chemistry by enabling one acid to be used with a variety of different C-terminus-functionalized intermediates.

  DOI：

  10.1080/00397910701648785
• 作为产物：
  描述：

  benzyl 4-formylamino-1-methylimidazole-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (9ci)-4-氨基-1-甲基-1H-咪唑-2-羧酸
  参考文献：
  名称：

  N‐Formamido‐Containing Mono‐ and Diheterocyclic Pyrrole‐and Imidazole‐2‐carboxylic Acids as Building Blocks for Polyamide Synthesis

  摘要：

  Four N-formamido-containing mono-and diheterocyclic pyrrole- and imidazole-2-containing acids 1-4 were synthesized as intermediates for the preparation of polyamide molecules. The N-formamido-moiety forces the compounds to bind strongly as a stacked dimer, and in a staggered fashion, at specific sequences in the minor-groove of DNA. The acid moiety at the C-terminus of compounds enables these molecules to be coupled to amine-containing intermediates to form the amide linkages of the target polyamide. This convergent approach increases the synthetic diversity in polyamide chemistry by enabling one acid to be used with a variety of different C-terminus-functionalized intermediates.

  DOI：

  10.1080/00397910701648785

文献信息

• Orthogonality and compatibility between Tsc and Fmoc amino-protecting groups
  作者：Jin Seok Choi、Hunhui Kang、Nakcheol Jeong、Hogyu Han

  DOI：10.1016/j.tet.2004.12.052

  日期：2005.2

  New deprotection conditions that provide a complete orthogonality between Tsc and Fmoc amino-protecting groups are described. The potential of these orthogonal deprotection conditions was then demonstrated by the efficient solid-phase synthesis of branched peptides 20 and 21 using doubly protected amino acids such as Tsc-Lys(Fmoc)-OH 4c and Fmoc-Lys(Tsc)-OH 4d.

  描述了在Tsc和Fmoc氨基保护基团之间提供完全正交性的新的脱保护条件。然后，通过使用双重保护的氨基酸（例如Tsc-Lys（Fmoc）-OH 4c和Fmoc-Lys（Tsc）-OH 4d）有效固相合成分支肽20和21，证明了这些正交脱保护条件的潜力。