(R)-4-(3-methoxyphenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone | 1614264-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-4-(3-methoxyphenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone
• 英文别名: 2-methylpropanoyloxymethyl (4R)-4-(3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 1614264-67-3
• 化学式: C₁₉H₂₃NO₆
• 分子量: 361.395
• InChiKey: XLYLZNFQAWLVDD-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-(3-methoxyphenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-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49%的产率得到(4R)-4-(3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylic acid
  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：

  (±)-4-(3-methoxyphenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-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 7.0h， 以69%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

文献信息

• Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives
  作者：Susana Y. Torres、Estael Ochoa、Yamila Verdecia、Francisca Rebolledo

  DOI：10.1016/j.tet.2014.05.012

  日期：2014.8

  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.