4-[(pivaloyloxy)methyl] 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylate | 510755-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[(pivaloyloxy)methyl] 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylate
• 英文别名: 4-O-(2,2-dimethylpropanoyloxymethyl) 3-O-methyl 5-O-propyl 2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylate
• CAS: 510755-91-6
• 化学式: C₂₀H₂₉NO₈
• 分子量: 411.452
• InChiKey: GEXSWTOGLBDSPO-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±50.0 °C(predicted)
• 密度：
  1.165±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[(pivaloyloxy)methyl] 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylate 在 lipase from Candida rugosa 作用下， 以 various solvents 、 乙腈 为溶剂， 反应 120.0h， 生成 (+)-3-(methoxycarbonyl)-2,6-dimethyl-5-(propoxycarbonyl)-1,4-dihydro-4-pyridinecarboxylic acid 、 (-)-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：

  methyl (E)-3-aminocrotonate 在 吗啉 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 4-[(pivaloyloxy)methyl] 3-methyl 5-propyl 2,6-dimethyl-1,4-dihydro-3,4,5-pyridinetricarboxylate
  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