N-(4-Bromobutyryl)-4-chloro-2-cyclohexyl-1,2-dihydropyridine | 146253-92-1

• 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: N-(4-Bromobutyryl)-4-chloro-2-cyclohexyl-1,2-dihydropyridine
• 英文别名: 4-bromo-1-(4-chloro-2-cyclohexyl-2H-pyridin-1-yl)butan-1-one
• CAS: 146253-92-1
• 化学式: C₁₅H₂₁BrClNO
• 分子量: 346.695
• InChiKey: VABWDKYWJQNQLK-UHFFFAOYSA-N

物化性质

• 沸点：
  449.7±45.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲氧基吡啶 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 三氯乙烯 为溶剂， 反应 0.5h， 生成 N-(4-Bromobutyryl)-4-chloro-2-cyclohexyl-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

文献信息

• Conversion of N-Acyl-2,3-dihydro-4-pyridones to 4-chloro-1,2-dihydropyridines using the Vilsmeier reagent.
  作者：Rima S. Al-awar、Sajan P. Joseph、Daniel L. Comins

  DOI：10.1016/0040-4039(93)88003-2

  日期：1992.12

  N-Acyl-2,3-dihydro-4-pyridones are converted to 1-acyl-4-chloro-1,2-dihydropyridines in one step using one equivalent of Vilsmeier reagent. This conversion was utilized in an asymmetric synthesis of (−)-coniine.

  使用一当量的Vilsmeier试剂一步将N-酰基-2,3-二氢-4-吡啶酮转化为1-酰基-4-氯-1,2-二氢吡啶。该转化被用于（-）-亚氨酸的不对称合成中。