4-Chloro-2-(4-chlorobutyl)-3-formyl-1-(phenoxycarbonyl)-1,2-dihydropyridine | 154050-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-Chloro-2-(4-chlorobutyl)-3-formyl-1-(phenoxycarbonyl)-1,2-dihydropyridine
• 英文别名: phenyl 4-chloro-2-(4-chlorobutyl)-3-formyl-2H-pyridine-1-carboxylate
• CAS: 154050-66-5
• 化学式: C₁₇H₁₇Cl₂NO₃
• 分子量: 354.233
• InChiKey: AHZJLMUYKYMUJS-UHFFFAOYSA-N

物化性质

• 沸点：
  456.0±45.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Chloro-2-(4-chlorobutyl)-3-formyl-1-(phenoxycarbonyl)-1,2-dihydropyridine 在 platinum on activated charcoal sodium tetrahydroborate 、 cerium(III) chloride 、 氢气 、 lithium carbonate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 27.08h， 生成 (2R*,3S*)-2-(4-chlorobutyl)-3-(hydroxymethyl)-1-(phenoxycarbonyl)piperidine
  参考文献：
  名称：

  Conversion of N-acyl-2,3-dihydro-4-pyridones to 4-chloro-1,2-dihydropyridines using the Vilsmeier Reagent. Synthesis of (-)-coniine and (±)-lupinine

  摘要：

  The full details are given of a study on the conversion of dihydropyridones of the type 3 to 4-chloro-1,2-dihydropyridines 4 using a Vilsmeier reagent. The use of 1 equiv of Vilsmeier reagent under mild conditions (ClCHCCl2, rt) transformed several racemic N-acyl-2,3-dihydro-4-pyridones 3 to dihydropyridines 4 in very good to excellent yields (83-96%). A C-3 methyl group can be tolerated as was demonstrated in the preparation of 4-chloro-3-methyl-1,2-dihydropyridine 7 from dihydropyridone 6 in 90 % yield. The utility of this conversion was demonstrated in the synthesis of the piperidine alkaloid, (-)-coniine. The synthesis of (-)-coniine was completed in five steps from 4-methoxy-3-(triisopropylsilyl)pyridine in 54% overall yield. When 2,3-dihydro-4-pyridones are treated with excess Vilsmeier reagent, good yields of 4-chloro-3-formyl-1,2-dihydropyridines result. These heterocycles are useful intermediates for alkaloid preparation, as was shown by two syntheses of the quinolizidine alkaloid, (+/-)-lupinine, carried out in three and five steps, respectively.

  DOI：

  10.1021/jo00079a018
• 作为产物：
  描述：

  氯甲酸苯酯 在 magnesium 、 1,2-二溴乙烷 、 三氯氧磷 作用下， 以 三氯乙烯 为溶剂， 反应 8.0h， 生成 4-Chloro-2-(4-chlorobutyl)-3-formyl-1-(phenoxycarbonyl)-1,2-dihydropyridine
  参考文献：
  名称：

  Conversion of N-acyl-2,3-dihydro-4-pyridones to 4-chloro-1,2-dihydropyridines using the Vilsmeier Reagent. Synthesis of (-)-coniine and (±)-lupinine

  摘要：

  The full details are given of a study on the conversion of dihydropyridones of the type 3 to 4-chloro-1,2-dihydropyridines 4 using a Vilsmeier reagent. The use of 1 equiv of Vilsmeier reagent under mild conditions (ClCHCCl2, rt) transformed several racemic N-acyl-2,3-dihydro-4-pyridones 3 to dihydropyridines 4 in very good to excellent yields (83-96%). A C-3 methyl group can be tolerated as was demonstrated in the preparation of 4-chloro-3-methyl-1,2-dihydropyridine 7 from dihydropyridone 6 in 90 % yield. The utility of this conversion was demonstrated in the synthesis of the piperidine alkaloid, (-)-coniine. The synthesis of (-)-coniine was completed in five steps from 4-methoxy-3-(triisopropylsilyl)pyridine in 54% overall yield. When 2,3-dihydro-4-pyridones are treated with excess Vilsmeier reagent, good yields of 4-chloro-3-formyl-1,2-dihydropyridines result. These heterocycles are useful intermediates for alkaloid preparation, as was shown by two syntheses of the quinolizidine alkaloid, (+/-)-lupinine, carried out in three and five steps, respectively.

  DOI：

  10.1021/jo00079a018