(S)-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide | 865316-85-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide
• 英文别名: N-[(1S)-1-phenylethyl]-5-propyl-1H-imidazole-4-carboxamide
• CAS: 865316-85-4
• 化学式: C₁₅H₁₉N₃O
• 分子量: 257.335
• InChiKey: KMGVUBQBNFCXPM-NSHDSACASA-N

物化性质

• 沸点：
  512.4±45.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-propyl-1H-imidazole-4-carboxylic acid (1-phenylethyl)amide 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(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
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 (9ci)-5-丙基-1H-咪唑-4-羰酰氯 反应 0.25h， 以92%的产率得到(S)-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

文献信息

• Participation of host ‘spacer’ atoms in carboxylic acid binding: implications for amino acid recognition
  作者：Daniel K. Barnhill、Andrew L. Sargent、William E. Allen

  DOI：10.1016/j.tet.2005.06.096

  日期：2005.8

  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.