2-bromo-N-(quinolin-8-yl)propanamide | 1161690-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-bromo-N-(quinolin-8-yl)propanamide
• 英文别名: 2-bromo-N-quinolin-8-ylpropanamide
• CAS: 1161690-16-9
• 化学式: C₁₂H₁₁BrN₂O
• 分子量: 279.136
• InChiKey: IYEFCJMQNZPJKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(quinolin-8-yl)propanamide 在 高氯酸 作用下， 反应 72.0h， 以67%的产率得到2-bromo-N-(quinolin-8-yl)propanamide perchlorate
  参考文献：
  名称：

  Interactions of amino acids, carboxylic acids, and mineral acids with different quinoline derivatives

  摘要：

  A series of quinoline containing receptors having amide and ester bonds are synthesized and characterised. The relative binding abilities of these receptors with various amino acids, carboxylic acids and mineral acids are determined by monitoring the changes in fluorescence intensity. Among the receptors bis(2-(quinolin-8-yloxy)ethyl) isophthalate shows fluorescence enhancement on addition of amino acids whereas the other receptors shows fluorescence quenching on addition of amino acids. The receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy) propanamide has higher binding affinity for amino acids. However, the receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide having similar structure do not bind to amino acids. This is attributed to the concave structure of the former which is favoured due to the presence of methyl substituent. The receptor bis(2-(quinolin-8-yloxy)ethyl) isophthalate do not bind to hydroxy carboxylic acids, but is a good receptor for dicarboxylic acids. The crystal structure of bromide and perchlorate salts of receptor 2-bromo-N-(quinolin-8-yl)-propanamide are determined. In both the cases the amide groups are not in the plane of quinoline ring. The structure of N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide, N-(2-methoxyphenethyl)-2-(quinolin-8-yloxy)acetamide and their salts with maleic acid as well as fumaric acid are determined. It is observed that the solid state structures are governed by the double bond geometry of these two acid. Maleic acid forms salt in both the cases, whereas fumaric acid forms either salt or co-crystals. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.01.040
• 作为产物：
  描述：

  8-氨基喹啉 、 2-溴丙酰溴 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromo-N-(quinolin-8-yl)propanamide
  参考文献：
  名称：

  α-[18F]氟酰胺与[18F]AgF的放射合成

  摘要：

  银促进的α-溴酰胺的亲核放射性氟化已被开发用于α-[ 18 F]氟酰胺的放射合成。反应条件简单且与伯、仲和叔 α-溴酰胺兼容。此外，该方法已成功应用于生物活性放射性示踪剂的合成，具有良好的放射化学转化率（RCC）和放射化学产率（RCY）。

  DOI：

  10.1055/s-0041-1738458

文献信息

• Selectivity in metal ions mediated C-N bond formation reactions of 8-aminoquinoline derivatives
  作者：Dipjyoti Kalita、Jubaraj B. Baruah

  DOI：10.1002/poc.1899

  日期：2012.2

  to be from methanol by deuterium labelling experiments. Whereas similar copper mediated reaction of I in ethanol led to nucleophilic substitution of bromide ion by ethoxide. The structures of the salts of fused heterocyclic compounds were determined and their fluorescence emissions were studied. The large difference in fluorescence emission of compound V formed from copper mediated reaction in ethanol

  通过2-溴N-（喹啉-8-基）丙酰胺（I）和2-溴N的C–N键形成的环化反应-（喹啉-8-基）乙酰胺（II）可通过金属盐（例如铜（+2），镍（+2）高氯酸盐或硝酸盐和乙酸钯（+2））来促进。镍（+2）高氯酸盐介导的I和II反应导致C–N键形成，从而给出了三个稠合六元杂环的相应高氯酸盐。发现铜（+2）介导的反应对I依赖于溶剂，但对II不依赖于溶剂。铜介导的II反应生成的环化产物类似于由II与高氯酸镍（+2）在甲醇或乙醇中反应获得的环化产物。但是，I与高氯酸铜（+2）在甲醇中的反应得到了C–N键合的甲氧基化环化产物。该反应分两步进行，环化然后进行甲氧基化。通过氘标记实验证实了甲氧基的来源是甲醇。而在乙醇中类似的铜介导的I反应导致乙醇离子对溴离子的亲核取代。确定了稠合杂环化合物的盐的结构，并研究了其荧光发射。由铜在乙醇中介导的反应形成的化合物V与在甲醇或乙醇中由镍介导的反应形成的化合物VI的荧光
• Interactions of amino acids, carboxylic acids, and mineral acids with different quinoline derivatives
  作者：Dipjyoti Kalita、Himangshu Deka、Shyam Sundar Samanta、Subrata Guchait、Jubaraj B. Baruah

  DOI：10.1016/j.molstruc.2011.01.040

  日期：2011.3

  A series of quinoline containing receptors having amide and ester bonds are synthesized and characterised. The relative binding abilities of these receptors with various amino acids, carboxylic acids and mineral acids are determined by monitoring the changes in fluorescence intensity. Among the receptors bis(2-(quinolin-8-yloxy)ethyl) isophthalate shows fluorescence enhancement on addition of amino acids whereas the other receptors shows fluorescence quenching on addition of amino acids. The receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy) propanamide has higher binding affinity for amino acids. However, the receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide having similar structure do not bind to amino acids. This is attributed to the concave structure of the former which is favoured due to the presence of methyl substituent. The receptor bis(2-(quinolin-8-yloxy)ethyl) isophthalate do not bind to hydroxy carboxylic acids, but is a good receptor for dicarboxylic acids. The crystal structure of bromide and perchlorate salts of receptor 2-bromo-N-(quinolin-8-yl)-propanamide are determined. In both the cases the amide groups are not in the plane of quinoline ring. The structure of N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide, N-(2-methoxyphenethyl)-2-(quinolin-8-yloxy)acetamide and their salts with maleic acid as well as fumaric acid are determined. It is observed that the solid state structures are governed by the double bond geometry of these two acid. Maleic acid forms salt in both the cases, whereas fumaric acid forms either salt or co-crystals. (C) 2011 Elsevier B.V. All rights reserved.