(9ci)-5-丙基-1H-咪唑-4-羰酰氯 | 459432-76-9

• 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)-5-丙基-1H-咪唑-4-羰酰氯
• 英文名称: 5-propyl-1H-imidazole-4-carbonyl chloride
• CAS: 459432-76-9
• 化学式: C₇H₉ClN₂O
• 分子量: 172.614
• InChiKey: QFTBZLXQAOGJJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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 24.08h， 生成 N-(3-methoxypropyl)-2-iodo-5-propyl-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  Anion Binding by Fluorescent Biimidazole Diamides

  摘要：

  Six 2,2'-biimidazoles with various amide groups at the 4- and 4'-positions were prepared from 5-propyl-1H-imidazole-4-carboxylic acid ethyl ester. In the final step of the synthesis, biimidazole C2-C2' bond formation was accomplished in 33-45% yield by palladium(0)-catalyzed homocoupling of the corresponding 2-iodoimidazoles. Four of the biimidazoles were studied by X-ray diffraction. In the solid state, all display coplanar imidazole rings, an anti relationship of amide groups, and intramolecular (NHamide...N-imid) and intermolecular (NHimid...O-amide) hydrogen bonding. In CH2Cl2, the emission intensity of the biimidazoles is quenched by the presence of dihydrogenphosphate and chloride anions, but no shifts in lambda(emiss) are observed. Binding constants for 1:1 biimidazole-anion complexation (K-assoc) are on the order of 10(4) M-1 for H2PO4- and Cl-. One of the receptors (bearing 3,5-difluorobenzylamides) is selective for chloride. The participation of the amide NH atoms in anion binding was established by H-1 NMR.

  DOI：

  10.1021/jo020098v
• 作为产物：
  描述：

  5-propyl-1H-imidazole-4-carboxylic acid hydrochloride 在 草酰氯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以71%的产率得到(9ci)-5-丙基-1H-咪唑-4-羰酰氯
  参考文献：
  名称：

  Biimidazole diamide anion binding agents

  摘要：

  本文描述了用于结合阴离子，如硫酸的双咪唑二酰胺化合物，以及其用途，例如从废水流中提取阴离子和/或检测阴离子。

  公开号：

  US20050004370A1

文献信息

• Biimidazole diamide anion binding agents
  申请人：Allen E. William

  公开号：US20050004370A1

  公开（公告）日：2005-01-06

  Biimidazole diamide compounds that are useful for binding anions such as sulfate are described, along with the use thereof for purposes such as extracting anions from a waste stream and/or detecting anions.

  本文描述了用于结合阴离子，如硫酸的双咪唑二酰胺化合物，以及其用途，例如从废水流中提取阴离子和/或检测阴离子。
• 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.
• US7078528B2
  申请人：——

  公开号：US7078528B2

  公开（公告）日：2006-07-18
• Anion Binding by Fluorescent Biimidazole Diamides
  作者：Corey P. Causey、William E. Allen

  DOI：10.1021/jo020098v

  日期：2002.8.1

  Six 2,2'-biimidazoles with various amide groups at the 4- and 4'-positions were prepared from 5-propyl-1H-imidazole-4-carboxylic acid ethyl ester. In the final step of the synthesis, biimidazole C2-C2' bond formation was accomplished in 33-45% yield by palladium(0)-catalyzed homocoupling of the corresponding 2-iodoimidazoles. Four of the biimidazoles were studied by X-ray diffraction. In the solid state, all display coplanar imidazole rings, an anti relationship of amide groups, and intramolecular (NHamide...N-imid) and intermolecular (NHimid...O-amide) hydrogen bonding. In CH2Cl2, the emission intensity of the biimidazoles is quenched by the presence of dihydrogenphosphate and chloride anions, but no shifts in lambda(emiss) are observed. Binding constants for 1:1 biimidazole-anion complexation (K-assoc) are on the order of 10(4) M-1 for H2PO4- and Cl-. One of the receptors (bearing 3,5-difluorobenzylamides) is selective for chloride. The participation of the amide NH atoms in anion binding was established by H-1 NMR.