bis[(isobutyryloxy)methyl] 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate | 442682-38-4

• 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: bis[(isobutyryloxy)methyl] 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 英文别名: 2,6-Dimethyl-4-[2-(difluoromethoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid bis[(isobutyryloxy)methyl] ester；bis(2-methylpropanoyloxymethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 442682-38-4
• 化学式: C₂₆H₃₁F₂NO₉
• 分子量: 539.53
• InChiKey: PEIRNTDKOZNZQI-UHFFFAOYSA-N

物化性质

• 沸点：
  592.1±50.0 °C(predicted)
• 密度：
  1.238±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis[(isobutyryloxy)methyl] 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 在 potassium carbonate 、 磷脂酶B 作用下， 以 异丙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (-)-3-[(isobutyryloxy)methyl] 5-methyl (4R)-4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  An efficient chemoenzymatic approach to enantiomerically pure 4-[2-(difluoromethoxy)phenyl] substituted 1,4-dihydropyridine-3,5-dicarboxylates

  摘要：

  An efficient chemoenzymatic synthesis of (-)-3-methyl 5-(2-propoxyethyl) (4R)-4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate has been achieved. The key step is a highly stereoselective Candida rugosa lipase (CRL)-mediated asymmetrisation of the prochiral bis[(isobutyryloxy)methyl]-4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00022-8
• 作为产物：
  描述：

  (二氟甲氧基)苯甲醛 在 氢氧化钾 、 ammonium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 bis[(isobutyryloxy)methyl] 4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  An efficient chemoenzymatic approach to enantiomerically pure 4-[2-(difluoromethoxy)phenyl] substituted 1,4-dihydropyridine-3,5-dicarboxylates

  摘要：

  An efficient chemoenzymatic synthesis of (-)-3-methyl 5-(2-propoxyethyl) (4R)-4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate has been achieved. The key step is a highly stereoselective Candida rugosa lipase (CRL)-mediated asymmetrisation of the prochiral bis[(isobutyryloxy)methyl]-4-[2-(difluoromethoxy)phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00022-8