5-O-[(2R)-1-(benzenesulfonyl)-3-hydroxypropan-2-yl] 3-O-ethyl (4R)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 1352187-22-4

• 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: 5-O-[(2R)-1-(benzenesulfonyl)-3-hydroxypropan-2-yl] 3-O-ethyl (4R)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1352187-22-4
• 化学式: C₂₆H₂₇Cl₂NO₇S
• 分子量: 568.475
• InChiKey: IJYGUGSYZYOQCN-UZUQRXQVSA-N

物化性质

• 沸点：
  739.3±60.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-[(2R)-1-(benzenesulfonyl)-3-hydroxypropan-2-yl] 3-O-ethyl (4R)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 、 sodium methylate 以 甲醇 为溶剂， 以80%的产率得到乙基甲基(4S)-4-(2,3-二氯苯基)-2,6-二甲基-1,4-二氢-3,5-吡啶二羧酸酯
  参考文献：
  名称：

  A facile synthesis of (S)-felodipine

  摘要：

  A short and facile synthesis of (S)-felodipine was developed starting from (R)-glycidol as the source of the chiral auxiliary. 2-Hydroxyethyl esters were found to undergo selective transesterification reactions in the presence of other esters. This selective transesterification reaction was applied to the synthesis of (S)-felodipine through selective substitution of the 2-hydroxyethyl group possessing chiral ester with sodium methoxide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.025
• 作为产物：
  描述：

  (2R)-1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-ol 在 哌啶 、 吡啶 、 Oxone 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 22.0h， 生成 5-O-[(2R)-1-(benzenesulfonyl)-3-hydroxypropan-2-yl] 3-O-ethyl (4R)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  A facile synthesis of (S)-felodipine

  摘要：

  A short and facile synthesis of (S)-felodipine was developed starting from (R)-glycidol as the source of the chiral auxiliary. 2-Hydroxyethyl esters were found to undergo selective transesterification reactions in the presence of other esters. This selective transesterification reaction was applied to the synthesis of (S)-felodipine through selective substitution of the 2-hydroxyethyl group possessing chiral ester with sodium methoxide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.025