(R)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone | 1614264-66-2

• 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: (R)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone
• 英文别名: 2-methylpropanoyloxymethyl (4R)-4-(4-bromophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 1614264-66-2
• 化学式: C₁₈H₂₀BrNO₅
• 分子量: 410.264
• InChiKey: OMZVGECTPJZNDA-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone 在 Candida antarctica lipase B 、 水 作用下， 以 甲醇 、 乙醚 、 甲基叔丁基醚 为溶剂， 反应 2.5h， 生成 methyl 4-(4-bromophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate
  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：

  氯甲基异酪酸盐 在 Candida antarctica lipase B 、 水 、 caesium carbonate 作用下， 以 甲基叔丁基醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (S)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-3,4-dihydro-2(1H)-pyridone 、 (R)-4-(4-bromophenyl)-6-methyl-5-[(2-methylpropanoyloxy)methyloxycarbonyl]-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 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.