(S)-2-iodo-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide | 865316-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-iodo-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide
• CAS: 865316-88-7
• 化学式: C₁₅H₁₈IN₃O
• 分子量: 383.232
• InChiKey: RUTHBNAIJGXWCA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.78
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-2-iodo-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide 在 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 以54%的产率得到(S,S)-5,5'-dipropyl-1H,1H'-[2,2']biimidazolyl-4,4'-dicarboxylic acid bis[(1-phenylethyl)amide]
  参考文献：
  名称：

  Participation of host ‘spacer’ atoms in carboxylic acid binding: implications for amino acid recognition

  摘要：

  Chiral 4,4'-diamidao-2,2'-biimidazoles were synthesized and found to bind N-Boc protected amino acids in CDCl3. The biinmidazole that features (R)-tetrahydrofurfuryl units discriminates between N-Boc-L-Ser (K-assoc 120 M-1) and its non-natural D-enantiomer (270 M-1). X-ray diffraction and computational analyses show that members of this receptor class adopt a cleft-like conformation, presenting a donor-spacer-donor-acceptor H-bonding array. Complexes of such biimidazoles with the COOH unit of amino acids are stabilized by direct involvement of what is nominally a 'spacer' atom. unlike other D-Sp-D-A hosts, (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.096
• 作为产物：
  描述：

  (9ci)-5-丙基-1H-咪唑-4-羰酰氯 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (S)-2-iodo-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide
  参考文献：
  名称：

  Participation of host ‘spacer’ atoms in carboxylic acid binding: implications for amino acid recognition

  摘要：

  Chiral 4,4'-diamidao-2,2'-biimidazoles were synthesized and found to bind N-Boc protected amino acids in CDCl3. The biinmidazole that features (R)-tetrahydrofurfuryl units discriminates between N-Boc-L-Ser (K-assoc 120 M-1) and its non-natural D-enantiomer (270 M-1). X-ray diffraction and computational analyses show that members of this receptor class adopt a cleft-like conformation, presenting a donor-spacer-donor-acceptor H-bonding array. Complexes of such biimidazoles with the COOH unit of amino acids are stabilized by direct involvement of what is nominally a 'spacer' atom. unlike other D-Sp-D-A hosts, (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.096