methyl (4R)-4-(3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate | 1614264-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (4R)-4-(3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 1614264-62-8
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: QIXOZLLBNAHMGA-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (±)-5-(tert-butoxycarbonyl)-4-(3-methoxyphenyl)-6-methyl-3,4-dihydro-2(1H)-pyridone 在 Candida antarctica lipase B 、 水 、 caesium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 甲基叔丁基醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 methyl (4R)-4-(3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-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

文献信息

• Chemoenzymatic synthesis of optically active phenolic 3,4-dihydropyridin-2-ones: a way to access enantioenriched 1,4-dihydropyridine and benzodiazepine derivatives
  作者：Susana Y. Torres、Rosario Brieva、Francisca Rebolledo

  DOI：10.1039/c7ob01066d

  日期：——

  A chemoenzymatic approach for the synthesis of optically active 4-(3-acetoxyphenyl)-5-(alkoxycarbonyl)-6-methyl-3,4-dihydropyridin-2-ones (3,4-DHP-2-ones) and their hydroxyphenyl derivatives has been developed, the key step being a Candida rugosa lipase (CRL)-catalyzed hydrolysis reaction. As a result, different optically active 3,4-DHP-2-ones have been prepared with very high enantiomeric excesses

  化学酶法合成光学活性的4-（3-乙酰氧基苯基）-5-（烷氧基羰基）-6-甲基-3,4-二氢吡啶-2-酮（3,4-DHP-2-酮）及其羟苯基已开发出衍生物，关键步骤是皱纹假丝酵母脂肪酶（CRL）催化的水解反应。结果，制备了具有很高对映体过量（ee = 94–99％）和良好收率的不同旋光性3,4-DHP-2-one。对映体富集的3,4-DHP-2-one已轻松转化为高度官能化的（R）-和（S）-1,4-二氢吡啶（1,4-DHPs）通过Vilsmeier-Haack反应获得。最后，使用TFA作为酸促进剂将1,4-DHP与苯-1,2-二胺偶联，为我们提供了相应的旋光杂合的1,5-苯并二氮杂-1,4-二氢吡啶（BZD-DHP）衍生物。在这些过程中未发生外消旋作用，并且以优异的产率获得了所有光学活性化合物。
• 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.