(±)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone | 1614264-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (±)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone
• CAS: 1614264-94-6
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: RNCDDHBFXDTGSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (±)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 sodium acetate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(±)-[2-(methyl)propanoyloxy]methyl 6-chloro-5-methanoyl-2-methyl-4-(1-naphthyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Chemoenzymatic approach to optically active 1,4-dihydropyridine derivatives

  摘要：

  A series of racemic (2-methyl)propanoyloxymethyl 4-ary1-6-chloro-5-methanoy1-2-methy1-1,4-dihydropyridine-3-carboxylates [(+/-)-5a-h] have been prepared by a four step sequence including a multicomponent Hantzsch process and a Vilsmeier-Haack reaction. The subsequent resolution of (+/-)-5a-h was carried out by means of lipase-catalyzed hydrolysis, the most adequate enzymes being lipases from Candida rugosa (CRL) and Candida antarctica (CAL-B). The moderate to high enantioselectivities values (E up to >200) obtained in most cases allowed us to obtain the corresponding optically active 1,4-dihydropyridine derivatives with high enantiomeric excesses (ee >= 94%) and yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.047
• 作为产物：
  描述：

  (±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone 在 水 、 caesium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 (±)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012