bis(2-cyanoethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate | 442682-35-1

• 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: bis(2-cyanoethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate
• CAS: 442682-35-1
• 化学式: C₂₂H₂₁F₂N₃O₅
• 分子量: 445.423
• InChiKey: NGHYYIDYAQCPJW-UHFFFAOYSA-N

物化性质

• 沸点：
  627.1±55.0 °C(predicted)
• 密度：
  1.278±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  121.44
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  bis(2-cyanoethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以73%的产率得到4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylic acid
  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 、 2-氰基乙酰乙酸乙酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以38%的产率得到bis(2-cyanoethyl) 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

文献信息

• An efficient chemoenzymatic approach to enantiomerically pure 4-[2-(difluoromethoxy)phenyl] substituted 1,4-dihydropyridine-3,5-dicarboxylates
  作者：Arkadij Sobolev、Maurice C.R. Franssen、Brigita Vigante、Brigita Cekavicus、Natalija Makarova、Gunars Duburs、Aede de Groot

  DOI：10.1016/s0957-4166(02)00022-8

  日期：2001.12

  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.