2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diacetoxymethyl ester | 145627-20-9

• 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: 2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diacetoxymethyl ester
• 英文别名: Bis(acetyloxymethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 145627-20-9
• 化学式: C₂₁H₂₂N₂O₁₀
• 分子量: 462.413
• InChiKey: JZBPBLAZVYZMRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diacetoxymethyl ester 在 水 作用下， 以 异丙醚 为溶剂， 反应 24.0h， 以87%的产率得到(R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monoacetoxymethyl ester
  参考文献：
  名称：

  Drastic solvent effect on lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines

  摘要：

  Two enantiomers of 1,4-dihydropyridine compounds have been obtained with high enantiomeric purity by lipase-catalyzed hydrolysis in organic solvent saturated with water. Enantioselectivity of this reaction is dependent on the solvent used.

  DOI：

  10.1016/s0040-4039(00)60861-4

文献信息

• Optically-active dihydropyridines via lipase-catalyzed enantioselective hydrolysis
  作者：Loreto Salazar、Charles J. Sih

  DOI：10.1016/0957-4166(95)00386-x

  日期：1995.12

  Several prochiral esters of 1,4-dihydropyridines were enantioselectively hydrolyzed by Pseudomonas lipases (AK, P-30, and K-10) and Candida cylindracea lipase (OF-360). The stereochemical preferences of the lipases P-30 and K-10 were found to be always 4-Pro R and that of OF-360 to be 4-Pro S. In contrast, the prochiral preference of the lipase AK varied depending on the substitution on the dihydropyridine ring. The N-methoxymethyl derivatives afforded the 4S isomers (95% ee) whereas the N-unsubstituted compounds yielded the 4R isomers (50-70% ee).