(1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol (S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate | 134028-03-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol (S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
• CAS: 134028-03-8
• 化学式: C₁₆H₁₆N₂O₆*C₁₉H₂₂N₂O
• 分子量: 626.709
• InChiKey: YAUFSFSQDCKNRC-SMIJEWCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  155.13
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol (S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 以84%的产率得到(S)-(+)-1,4-二氢-2,6-二甲基-4-(3-硝基苯基)-3,5-吡啶二甲酸单甲酯
  参考文献：
  名称：

  Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

  摘要：

  An efficient total synthesis of (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in high optical purities is reported. The useful step is the resolution of racemic 2, 6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid by using commercially available Cinchona alkaloids cinchonidine and quinidine as the resolving agents. Under the optimum conditions, the optical purities for R- and S-enantiomers are extremely high (ee >99.5%). The further dihydropyridine receptor binding activity assay shows that the S-enantiomer is more potent than R- enantiomer both in rat cardiac (approximately 19 times) and cerebral cortex membrane (12 times). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.104
• 作为产物：
  描述：

  辛可尼丁 、 2,6-二甲基-5-甲氧羰基-4-(3-硝基苯基)-1,4-二氢吡啶-3-羧酸 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 18.25h， 以41%的产率得到(1R)-quinolin-4-yl((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol (S)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

  摘要：

  An efficient total synthesis of (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate in high optical purities is reported. The useful step is the resolution of racemic 2, 6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid by using commercially available Cinchona alkaloids cinchonidine and quinidine as the resolving agents. Under the optimum conditions, the optical purities for R- and S-enantiomers are extremely high (ee >99.5%). The further dihydropyridine receptor binding activity assay shows that the S-enantiomer is more potent than R- enantiomer both in rat cardiac (approximately 19 times) and cerebral cortex membrane (12 times). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.104