(2R)-1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl 3-oxobutanoate | 1215080-62-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2R)-1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl 3-oxobutanoate
• 英文别名: [(2R)-1-(oxan-2-yloxy)-3-phenylsulfanylpropan-2-yl] 3-oxobutanoate
• CAS: 1215080-62-8
• 化学式: C₁₈H₂₄O₅S
• 分子量: 352.452
• InChiKey: XSKZROMNBDQQNW-NNJIEVJOSA-N

物化性质

• 沸点：
  508.5±50.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R)-1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl 3-oxobutanoate 在 哌啶 、 吡啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  2H-吡喃,四氢-2-[(2S)-噁丙环基甲氧基]- 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 丙酮 、 mineral oil 为溶剂， 反应 4.5h， 生成 (2R)-1-(phenylthio)-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl 3-oxobutanoate
  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

文献信息

• [EN] PROCESS FOR PREPARING (S)-(-)-FELODIPINE<br/>[FR] PROCEDE DE PREPARATION DE (S)-(-)-FELODIPINE
  申请人：AHN GOOK PHARMACEUTICAL CO LTD

  公开号：WO2010027113A2

  公开（公告）日：2010-03-11

  The embodiment proposes a method for preparing (S)-(-)- ethyl methyl 4-(2,3-dichlorophenyl)- 1,4-dihydro-2,6-dimethyl-3,5-pyridine- dicarboxylate (hereinafter, referring to as "(S)-(-)-felodipine", and more particularly, a method for effectively preparing the (S)-(-)-felodipine through a selective transesterification of -hydroxy ester after synthesizing a felodipine derivate including a chiral separation compound and isolating (S)-isomers. The chiral separation compound is synthesized from (R)-glycidol or (S)-glycidol through reaction with various nucleophiles and epoxide.
• A facile synthesis of (S)-felodipine
  作者：Kuktae Kwon、Jung A. Shin、Hee-Yoon Lee

  DOI：10.1016/j.tet.2011.10.025

  日期：2011.12

  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.