1-(4-chlorophenyl)-2-N,N-dibenzylamino-1-propanone | 33426-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chlorophenyl)-2-N,N-dibenzylamino-1-propanone
• 英文别名: 1-(4-Chlorophenyl)-2-(dibenzylamino)propan-1-one
• CAS: 33426-80-1
• 化学式: C₂₃H₂₂ClNO
• 分子量: 363.887
• InChiKey: BWEXIEMYSOARBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.173
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-N,N-dibenzylamino-1-propanone 在 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 氢氟酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2-N,N-dibenzylamino-1-(4-[18F]fluorophenyl)-1-propanone
  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：

  4-氯苯丙酮 在 溴 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 2.0h， 生成 1-(4-chlorophenyl)-2-N,N-dibenzylamino-1-propanone
  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

文献信息

• 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.