3-allyl 5-methyl (4R)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate | 167700-27-8

• 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: 3-allyl 5-methyl (4R)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS: 167700-27-8
• 化学式: C₁₉H₁₉Cl₂NO₄
• 分子量: 396.27
• InChiKey: CCXJCRVPZXIYLX-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-allyl 5-methyl (4R)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate 在 吗啉 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以62%的产率得到(4S)-4-(2,3-dichlorophenyl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethylpyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of Optically Pure 1,4-Dihydropyridine Derivatives by Means of Diastereoisomeric Separation of the Hantzsch Intermediates Bearing (R)-1-Phenylethylamino Group

  摘要：

  Hantzsch intermediates, which were obtained by Michael addition reaction of benzylideneacetoacetates with the enamino esters bearing (R)-1-phenylethylamino group as a chiral auxiliary, were separated into two diastereoisomeric mixtures. Each of them underwent cyclization reaction to give optically pure 1,4-dihydropyridine derivatives.

  DOI：

  10.3987/com-94-s(b)51
• 作为产物：
  描述：

  allyl 3-((1R)-1-phenylethyl)aminocrotonate 在 ammonium hydroxide 、 正丁基锂 、 silica gel 作用下， 反应 6.5h， 生成 3-allyl 5-methyl (4R)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of Optically Pure 1,4-Dihydropyridine Derivatives by Means of Diastereoisomeric Separation of the Hantzsch Intermediates Bearing (R)-1-Phenylethylamino Group

  摘要：

  Hantzsch intermediates, which were obtained by Michael addition reaction of benzylideneacetoacetates with the enamino esters bearing (R)-1-phenylethylamino group as a chiral auxiliary, were separated into two diastereoisomeric mixtures. Each of them underwent cyclization reaction to give optically pure 1,4-dihydropyridine derivatives.

  DOI：

  10.3987/com-94-s(b)51