(4S)-3-ethyl 5-(1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl) 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 1215080-64-0

• 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: (4S)-3-ethyl 5-(1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl) 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 3-O-ethyl 5-O-[(2R)-1-(oxan-2-yloxy)-3-phenylsulfanylpropan-2-yl] 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1215080-64-0
• 化学式: C₃₁H₃₅Cl₂NO₆S
• 分子量: 620.594
• InChiKey: PBCVVSONKIMGMQ-JJFHMGRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S)-3-ethyl 5-(1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl) 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 在 Oxone 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 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：

  2H-吡喃,四氢-2-[(2S)-噁丙环基甲氧基]- 在 哌啶 、 吡啶 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 丙酮 、 mineral oil 、 苯 为溶剂， 反应 10.5h， 生成 (4S)-3-ethyl 5-(1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl) 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