(±)-5-(acetoxymethyloxycarbonyl)-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2-(1H)-pyridone | 1614264-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-5-(acetoxymethyloxycarbonyl)-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2-(1H)-pyridone
• 英文别名: acetyloxymethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 1614264-63-9
• 化学式: C₁₆H₁₆N₂O₇
• 分子量: 348.312
• InChiKey: NVSJBCDAQURDLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (±)-5-(acetoxymethyloxycarbonyl)-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2-(1H)-pyridone 在 Candida antarctica lipase B 、 水 作用下， 以 甲基叔丁基醚 为溶剂， 反应 2.0h， 以91%的产率得到
  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：

  (±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(3-nitrophenyl)-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， 生成 (±)-5-(acetoxymethyloxycarbonyl)-6-methyl-4-(3-nitrophenyl)-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

• US20140275042A1
  申请人：——

  公开号：US20140275042A1

  公开（公告）日：2014-09-18