3-(methoxycarbonyl)-2,6-dimethyl-5-(propoxycarbonyl)-1,4-dihydro-4-pyridinecarboxylic acid | 510755-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(methoxycarbonyl)-2,6-dimethyl-5-(propoxycarbonyl)-1,4-dihydro-4-pyridinecarboxylic acid
• 英文别名: 3-Methoxycarbonyl-2,6-dimethyl-5-propoxycarbonyl-1,4-dihydropyridine-4-carboxylic acid；3-methoxycarbonyl-2,6-dimethyl-5-propoxycarbonyl-1,4-dihydropyridine-4-carboxylic acid
• CAS: 510755-86-9；510755-93-8；510755-97-2
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: RZYPVGLDQHEYBT-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±45.0 °C(predicted)
• 密度：
  1.230±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(methoxycarbonyl)-2,6-dimethyl-5-(propoxycarbonyl)-1,4-dihydro-4-pyridinecarboxylic acid 在 lipase from Candida antarctica (Novozym 435(R)) 、 potassium carbonate 作用下， 以 异丙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 (-)-3-(methoxycarbonyl)-2,6-dimethyl-5-(propoxycarbonyl)-1,4-dihydro-4-pyridinecarboxylic acid
  参考文献：
  名称：

  Enantioselective lipase-catalysed kinetic resolution of acyloxymethyl and ethoxycarbonylmethyl esters of 1,4-dihydroisonicotinic acid derivatives

  摘要：

  The lipase-catalysed kinetic resolution of four derivatives of 4-[(acyloxy)methyl] and 4-ethoxycarbonylmethyl 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylates has been investigated. Whereas the enantioselectivity of lipases towards the acyloxymethyl derivatives was rather low, the Candida antarctica lipase B (Novozym 435(R), CAL-B)-catalysed hydrolysis of the ethoxycarbonylmethyl ester of 1,4-dihydroisonicotinic acid was enantioselective. In water-saturated diisopropyl ether at 45degreesC the enantioselectivity of CAL-B toward the ethoxycarbonylmethyl ester was rather moderate (E = 13.8), but it was enhanced at rt and +4degreesC (E = 21.5 and E = 28.9, respectively). A high enantiomeric ratio (E = 45.3) was reached at subzero temperatures, although at the expense of the reaction rate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00655-9
• 作为产物：
  描述：

  乙酰乙酸正丙酯 、 methyl (E)-3-aminocrotonate 、 乙醛酸 在 吗啉 、 乙酸酐 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 32.5h， 以12.6%的产率得到3-(methoxycarbonyl)-2,6-dimethyl-5-(propoxycarbonyl)-1,4-dihydro-4-pyridinecarboxylic acid
  参考文献：
  名称：

  Enantioselective lipase-catalysed kinetic resolution of acyloxymethyl and ethoxycarbonylmethyl esters of 1,4-dihydroisonicotinic acid derivatives

  摘要：

  The lipase-catalysed kinetic resolution of four derivatives of 4-[(acyloxy)methyl] and 4-ethoxycarbonylmethyl 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylates has been investigated. Whereas the enantioselectivity of lipases towards the acyloxymethyl derivatives was rather low, the Candida antarctica lipase B (Novozym 435(R), CAL-B)-catalysed hydrolysis of the ethoxycarbonylmethyl ester of 1,4-dihydroisonicotinic acid was enantioselective. In water-saturated diisopropyl ether at 45degreesC the enantioselectivity of CAL-B toward the ethoxycarbonylmethyl ester was rather moderate (E = 13.8), but it was enhanced at rt and +4degreesC (E = 21.5 and E = 28.9, respectively). A high enantiomeric ratio (E = 45.3) was reached at subzero temperatures, although at the expense of the reaction rate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00655-9

文献信息

• Enantioselective lipase-catalysed kinetic resolution of acyloxymethyl and ethoxycarbonylmethyl esters of 1,4-dihydroisonicotinic acid derivatives
  作者：Arkadij Sobolev、Maurice C.R. Franssen、Janis Poikans、Gunars Duburs、Aede de Groot

  DOI：10.1016/s0957-4166(02)00655-9

  日期：2002.10

  The lipase-catalysed kinetic resolution of four derivatives of 4-[(acyloxy)methyl] and 4-ethoxycarbonylmethyl 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylates has been investigated. Whereas the enantioselectivity of lipases towards the acyloxymethyl derivatives was rather low, the Candida antarctica lipase B (Novozym 435(R), CAL-B)-catalysed hydrolysis of the ethoxycarbonylmethyl ester of 1,4-dihydroisonicotinic acid was enantioselective. In water-saturated diisopropyl ether at 45degreesC the enantioselectivity of CAL-B toward the ethoxycarbonylmethyl ester was rather moderate (E = 13.8), but it was enhanced at rt and +4degreesC (E = 21.5 and E = 28.9, respectively). A high enantiomeric ratio (E = 45.3) was reached at subzero temperatures, although at the expense of the reaction rate. (C) 2002 Elsevier Science Ltd. All rights reserved.