2-Azido-1-(4-chloro-phenyl)-propan-1-one | 875289-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Azido-1-(4-chloro-phenyl)-propan-1-one
• 英文别名: 2-Azido-1-(4-chlorophenyl)propan-1-one
• CAS: 875289-86-4
• 化学式: C₉H₈ClN₃O
• 分子量: 209.635
• InChiKey: VHHANYYJLJUBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Azido-1-(4-chloro-phenyl)-propan-1-one 在 盐酸 、 sodium carbonate 、 亚磷酸三乙酯 作用下， 以 水 、 甲苯 为溶剂， 生成 N-[2-(4-Chlorophenyl)-1-methyl-2-oxoethyl]acetamide
  参考文献：
  名称：

  N.C.A.18F-labelled norephedrine derivatives via α-aminopropiophenones

  摘要：

  N-protected 2-anlino-1-([F-18]fluorophenyl)-1-propanones are interesting fluorine-18 labelled intermediates to synthesize potential PET-tracers for mapping the adrenergic nervous system of the heart. Several N-protected alpha -aminoalkylarylketones were prepared to examine the direct nucleophilic n.c.a. F-18-fluorination of these carbonyl activated precursors. The influence of different protecting groups, the kind of leaving group and the stereoselective reduction of the keto function have been investigated in order to optimize the radiotracer production. It was shown that the F-18-substitution of the para-trimethylammonium group, e.g. of N-dibenzylated propiophenone, leads to radiochemical yields of up to 60%. The stereoselective reduction of the carbonyl function with formation of the n.c.a. erythro 2-N,N-dibenzylamino-1-(4-[F-18]fluorophenyl)-1-propanol was performed using BH3. THF. The diastereomeric excess was about 80%. Hydrogenolytical debenzylation was achieved with ammonium formiate in presence of palladium on charcoal to give the 4-[F-18]fluoronorephedrine with a radiochemical yield of 15-20% within a total time of 60 min.

  DOI：

  10.1002/1099-1344(200012)43:14<1345::aid-jlcr424>3.0.co;2-n
• 作为产物：
  描述：

  [1-(4-Chlorophenyl)-1-oxopropan-2-yl] 4-nitrobenzenesulfonate 在 sodium azide 作用下， 生成 2-Azido-1-(4-chloro-phenyl)-propan-1-one
  参考文献：
  名称：

  An Effective Synthesis of α-Azido Ketones From Ketones

  摘要：

  One-pot transformation of ketones into alpha -azido ketones has been achieved by successive treatment with HNIB and NaN3 in acetonitrile.

  DOI：

  10.1080/00397910008087049

文献信息

• Structural spectroscopic study of enantiomerically pure synthetic cathinones and their major metabolites
  作者：Dita Spálovská、Martin Paškan、Bronislav Jurásek、Martin Kuchař、Michal Kohout、Vladimír Setnička

  DOI：10.1039/d0nj05065b

  日期：——

  structure is crucial. Here, we present a comprehensive spectroscopic structural study of synthetic cathinones (clephedrone, flephedrone, and brephedrone) and their major human metabolites, desmethyl derivatives. Chiral high-performance liquid chromatography was utilized to obtain the individual enantiomers of the parent synthetic cathinones and their assumed major metabolites synthesized de novo. The

  新的精神活性物质（NPS）已成为非法滥用药物的流行替代品。但是，要确定它们在人体中的代谢途径，对其结构的详细了解至关重要。在这里，我们对合成的卡西酮（麻黄酮，麻黄酮和麻黄酮）及其主要的人体代谢产物去甲基衍生物进行了全面的光谱结构研究。手性高效液相色谱用于获得母体合成卡西酮的单个对映异构体及其从头合成的主要代谢产物。所开发的色谱方法使得有可能以毫克级获得目标光学纯物质。电子和振动圆二色性，结合红外和紫外光谱并得到DFT计算的支持，以确定它们的绝对构型和手法，以详细阐明其分子结构。在水溶液中发现每种物质的两个稳定构象异构体。根据玻尔兹曼分布估计它们的相对丰度，并获得种群加权光谱。实验光谱和模拟光谱之间实现了非常好的一致性，从而可以在水溶液中确定所研究物质的3D结构。
• Ermert, J.; Hamacher, K.; Coenen, H. H., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 53 - 55
  作者：Ermert, J.、Hamacher, K.、Coenen, H. H.

  DOI：——

  日期：——
• An Effective Synthesis of α-Azido Ketones From Ketones
  作者：Jong Chan Lee、Sehyun Kim、Woo Choul Shin

  DOI：10.1080/00397910008087049

  日期：2000.12

  One-pot transformation of ketones into alpha -azido ketones has been achieved by successive treatment with HNIB and NaN3 in acetonitrile.
• N.C.A.18F-labelled norephedrine derivatives via α-aminopropiophenones
  作者：J. Ermert、K. Hamacher、H. H. Coenen

  DOI：10.1002/1099-1344(200012)43:14<1345::aid-jlcr424>3.0.co;2-n

  日期：2000.12

  N-protected 2-anlino-1-([F-18]fluorophenyl)-1-propanones are interesting fluorine-18 labelled intermediates to synthesize potential PET-tracers for mapping the adrenergic nervous system of the heart. Several N-protected alpha -aminoalkylarylketones were prepared to examine the direct nucleophilic n.c.a. F-18-fluorination of these carbonyl activated precursors. The influence of different protecting groups, the kind of leaving group and the stereoselective reduction of the keto function have been investigated in order to optimize the radiotracer production. It was shown that the F-18-substitution of the para-trimethylammonium group, e.g. of N-dibenzylated propiophenone, leads to radiochemical yields of up to 60%. The stereoselective reduction of the carbonyl function with formation of the n.c.a. erythro 2-N,N-dibenzylamino-1-(4-[F-18]fluorophenyl)-1-propanol was performed using BH3. THF. The diastereomeric excess was about 80%. Hydrogenolytical debenzylation was achieved with ammonium formiate in presence of palladium on charcoal to give the 4-[F-18]fluoronorephedrine with a radiochemical yield of 15-20% within a total time of 60 min.