4-bromo-N,N'-diethylbenzamidine | 346448-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-N,N'-diethylbenzamidine
• 英文别名: 4-bromo-N,N'-diethylbenzenecarboximidamide
• CAS: 346448-60-0；661485-27-4
• 化学式: C₁₁H₁₅BrN₂
• 分子量: 255.157
• InChiKey: ZFCSDLVNKFXIRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-N,N'-diethylbenzamidine 在 盐酸 作用下， 生成 4-bromo-N,N-diethylbenzamidinium chloride
  参考文献：
  名称：

  Noncovalent Interactions between Tetrazole and an N,N‘-Diethyl-Substituted Benzamidine

  摘要：

  Amidines have long been known to form strong noncovalent complexes with carboxylates and phosphates. However, their interaction with tetrazoles, which are acidic heterocycles and important bioisosteric replacements for carboxylic acids in medicinal chemistry, has remained unexplored so far. The binding of a tetrazole to an N,N'-diethyl-substituted benzamidine has been studied for the first time by X-ray crystallography, solution NMR methods, and electrospray mass; spectrometry. The amidinium group of model complex 3 was found to prefer an E,Z configuration in the crystal. Benzamidinium and tetrazolate groups alternate along an infinite chain of hydrogen bonds and salt bridges between the amidine-NH groups and the two tetrazole-N atoms next to the ring carbon. In solution, a 1:1 complex was evident from Job's method of continuous variation, and an association constant of 4.0 x 10(3) +/- 1.6 x 10(3) M-1 (in CDCl3/CD3CN, 6:1) could be determined by H-1 NMR dilution experiments. Tetrazolate was not only found to be a weaker ligand than carboxylates but, surprisingly, the binding mode also changed with concentration in neat CDCl3. At low concentrations, the amidine group in complex 3 adapted an E,E configuration as it does in a related carboxylic acid complex 4. With increasing concentration, the E,Z isomer starts to predominate. A free activation enthalpy DeltaG(298)(double dagger) of 64 +/- 1 kJ mol(-1) for the E,E to E,Z isomerization was determined by line shape analysis at different magnetic fields. Binding strength was further probed in a competition experiment between a bisamidine, a carboxylate, and a tetrazolate by electrospray mass spectrometry.

  DOI：

  10.1021/jo005632i
• 作为产物：
  描述：

  N-乙基-4-溴苯甲酰胺 以 乙醇 、 二氯甲烷 为溶剂， 反应 144.0h， 生成 4-bromo-N,N'-diethylbenzamidine
  参考文献：
  名称：

  Noncovalent Interactions between Tetrazole and an N,N‘-Diethyl-Substituted Benzamidine

  摘要：

  Amidines have long been known to form strong noncovalent complexes with carboxylates and phosphates. However, their interaction with tetrazoles, which are acidic heterocycles and important bioisosteric replacements for carboxylic acids in medicinal chemistry, has remained unexplored so far. The binding of a tetrazole to an N,N'-diethyl-substituted benzamidine has been studied for the first time by X-ray crystallography, solution NMR methods, and electrospray mass; spectrometry. The amidinium group of model complex 3 was found to prefer an E,Z configuration in the crystal. Benzamidinium and tetrazolate groups alternate along an infinite chain of hydrogen bonds and salt bridges between the amidine-NH groups and the two tetrazole-N atoms next to the ring carbon. In solution, a 1:1 complex was evident from Job's method of continuous variation, and an association constant of 4.0 x 10(3) +/- 1.6 x 10(3) M-1 (in CDCl3/CD3CN, 6:1) could be determined by H-1 NMR dilution experiments. Tetrazolate was not only found to be a weaker ligand than carboxylates but, surprisingly, the binding mode also changed with concentration in neat CDCl3. At low concentrations, the amidine group in complex 3 adapted an E,E configuration as it does in a related carboxylic acid complex 4. With increasing concentration, the E,Z isomer starts to predominate. A free activation enthalpy DeltaG(298)(double dagger) of 64 +/- 1 kJ mol(-1) for the E,E to E,Z isomerization was determined by line shape analysis at different magnetic fields. Binding strength was further probed in a competition experiment between a bisamidine, a carboxylate, and a tetrazolate by electrospray mass spectrometry.

  DOI：

  10.1021/jo005632i

文献信息

• BACTERIAL EFFLUX PUMP INHIBITORS FOR THE TREATMENT OF OPHTHALMIC AND OTIC INFECTIONS
  申请人：Bostian Keith

  公开号：US20080132457A1

  公开（公告）日：2008-06-05

  Efflux pump inhibitors are co-administered with antimicrobial agents for the treatment of ophthalmic or otic infections. The agents may be co-administered directly to the site of infection (e.g., the eye or ear).

  流出泵抑制剂与抗微生物药物一起联合使用，用于治疗眼科或耳科感染。这些药物可以直接共同应用于感染部位（例如眼睛或耳朵）。
• US7947741B2
  申请人：——

  公开号：US7947741B2

  公开（公告）日：2011-05-24
• US7994225B2
  申请人：——

  公开号：US7994225B2

  公开（公告）日：2011-08-09
• Noncovalent Interactions between Tetrazole and an <i>N</i>,<i>N</i>‘-Diethyl-Substituted Benzamidine
  作者：Lars Peters、Roland Fröhlich、Alan S. F. Boyd、Arno Kraft

  DOI：10.1021/jo005632i

  日期：2001.5.1

  Amidines have long been known to form strong noncovalent complexes with carboxylates and phosphates. However, their interaction with tetrazoles, which are acidic heterocycles and important bioisosteric replacements for carboxylic acids in medicinal chemistry, has remained unexplored so far. The binding of a tetrazole to an N,N'-diethyl-substituted benzamidine has been studied for the first time by X-ray crystallography, solution NMR methods, and electrospray mass; spectrometry. The amidinium group of model complex 3 was found to prefer an E,Z configuration in the crystal. Benzamidinium and tetrazolate groups alternate along an infinite chain of hydrogen bonds and salt bridges between the amidine-NH groups and the two tetrazole-N atoms next to the ring carbon. In solution, a 1:1 complex was evident from Job's method of continuous variation, and an association constant of 4.0 x 10(3) +/- 1.6 x 10(3) M-1 (in CDCl3/CD3CN, 6:1) could be determined by H-1 NMR dilution experiments. Tetrazolate was not only found to be a weaker ligand than carboxylates but, surprisingly, the binding mode also changed with concentration in neat CDCl3. At low concentrations, the amidine group in complex 3 adapted an E,E configuration as it does in a related carboxylic acid complex 4. With increasing concentration, the E,Z isomer starts to predominate. A free activation enthalpy DeltaG(298)(double dagger) of 64 +/- 1 kJ mol(-1) for the E,E to E,Z isomerization was determined by line shape analysis at different magnetic fields. Binding strength was further probed in a competition experiment between a bisamidine, a carboxylate, and a tetrazolate by electrospray mass spectrometry.