(±)-5-(tert-butoxycarbonyl)-6-methyl-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone | 1614264-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (±)-5-(tert-butoxycarbonyl)-6-methyl-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone
• CAS: 1614264-86-6
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: MSLBBJKORKLQED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (±)-5-(tert-butoxycarbonyl)-6-methyl-4-(1-naphthyl)-3,4-dihydro-2(1H)-pyridone 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(±)-5-carboxy-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
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 乙酰乙酸叔丁酯 、 1-萘甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 6.0h， 以92%的产率得到(±)-5-(tert-butoxycarbonyl)-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

文献信息

• Chemoenzymatic approach to optically active 1,4-dihydropyridine derivatives
  作者：Susana Y. Torres、Yamila Verdecia、Francisca Rebolledo

  DOI：10.1016/j.tet.2015.04.047

  日期：2015.6

  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.