2,6-Dimethyl-1,4-dihydro-pyridine-3,4,5-tricarboxylic acid 3,5-dipropyl ester | 157490-63-6

• 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: 2,6-Dimethyl-1,4-dihydro-pyridine-3,4,5-tricarboxylic acid 3,5-dipropyl ester
• 英文别名: 3,5-Dipropyl 1,4-dihydro-2,6-dimethyl-3,4,5-pyridinetricarboxylate；2,6-dimethyl-3,5-bis(propoxycarbonyl)-1,4-dihydropyridine-4-carboxylic acid
• CAS: 157490-63-6
• 化学式: C₁₆H₂₃NO₆
• 分子量: 325.362
• InChiKey: KFZBLPOJWMDIPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2,6-Dimethyl-1,4-dihydro-pyridine-3,4,5-tricarboxylic acid 3,5-dipropyl ester 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 sodium 2-(2,6-dimethyl-3,5-di-n-propoxycarbonyl-1,4-dihydroisonicotinoyl)aminoethane sulfonate
  参考文献：
  名称：

  The derivatives of 2,6-dimethyl-1,4-dihydroisonicotinic acid and their antiplatelet properties

  摘要：

  DOI：

  10.1016/0223-5234(94)90103-1
• 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

• The derivatives of 2,6-dimethyl-1,4-dihydroisonicotinic acid and their antiplatelet properties
  作者：J Poikáns、G Tirzítis、E Bisenieks、J Uldrikis、VS Gurevich、IA Mikhailova、G Duburs

  DOI：10.1016/0223-5234(94)90103-1

  日期：1994.1
• 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.