(±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone | 1614264-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone
• CAS: 1614264-75-3
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: UCCYRRPKTFBJEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.19
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 2-cyanoethyl 2-oxobutanoate 、 1-萘甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 7.0h， 以52%的产率得到(±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-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