(S)-1-(4-hydroxymethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one | 352233-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(4-hydroxymethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one
• 英文别名: (2S)-1-[4-(hydroxymethyl)phenyl]-2-methyl-3-piperidin-1-ylpropan-1-one
• CAS: 352233-17-1
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: MBFHFUBFALKDKH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-hydroxymethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one 在 palladium on activated charcoal chromium(VI) oxide 、 硫酸 、 氢气 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 1.75h， 生成 (1S,2S)-1-(4-carboxyphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-ol hydrochloride
  参考文献：
  名称：

  外消旋和旋光形式的一些托哌酮代谢物的合成

  摘要：

  1-（4'-羧基苯基）-2-甲基-3-（哌啶-1-基）-丙烷-1-酮M3，赤型-1-（4'-羧苯基）-2-甲基-3-（哌啶- 1-yl）-丙-1-醇M4和苏式-1-（4'-羧苯基）-2-甲基-3-（哌啶-1-基）-丙-1-醇M5，肌肉松弛药甲苯哌立松的代谢产物以外消旋和旋光形式合成。

  DOI：

  10.1016/s0957-4166(02)00025-3
• 作为产物：
  描述：

  4'-acetoxymethylpropiophenone 在 盐酸 、 sodium hydroxide 、 乙醇 、 水 作用下， 以 甲醇 为溶剂， 反应 4.25h， 生成 (S)-1-(4-hydroxymethylphenyl)-2-methyl-3-(piperidin-1-yl)propan-1-one
  参考文献：
  名称：

  Synthesis, resolution and absolute configuration of a tolperisone metabolite

  摘要：

  1-(4'-Hydroxymethyl-phenyl)-2-methyl-3-(piperidine-1-yl)-propane-1-one M2, a metabolite of tolperisone, was synthesised in a solvent-free Mannich reaction. The optical resolution was carried out by diastereoisomeric salt formation and separation, for which three resolving agents ((2R,3R)-O,O'-dibenzoyl tartaric acid, (2R,3R)-O,O'-di-p-toluoyl tartaric acid and (R)-2-hydroxy-4-(2-methoxyphenyl)-5.5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide (anicyphos)) were found. The absolute configuration of M2 was determined by the single-crystal X-ray diffraction method. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00088-x

文献信息

• Synthesis of some tolperisone metabolites in racemic and optically active form
  作者：József Bálint、Gabriella Egri、Imre Markovits、Mátyás Czugler、Katalin Marthi、Ádám Demeter、Krisztina Temesvári-Takács、Elemér Fogassy

  DOI：10.1016/s0957-4166(02)00025-3

  日期：2002.1

  -methyl-3-(piperidine-1-yl)-propan-1-ol M4 and threo-1-(4′-carboxyphenyl)-2-methyl-3-(piperidine-1-yl)-propan-1-ol M5, metabolites of the muscle relaxant tolperisone were synthesized in racemic and optically active forms.

  1-（4'-羧基苯基）-2-甲基-3-（哌啶-1-基）-丙烷-1-酮M3，赤型-1-（4'-羧苯基）-2-甲基-3-（哌啶- 1-yl）-丙-1-醇M4和苏式-1-（4'-羧苯基）-2-甲基-3-（哌啶-1-基）-丙-1-醇M5，肌肉松弛药甲苯哌立松的代谢产物以外消旋和旋光形式合成。
• Synthesis, resolution and absolute configuration of a tolperisone metabolite
  作者：József Bálint、Imre Markovits、Gabriella Egri、Zsuzsanna Tuza、László Párkányi、Elemér Fogassy

  DOI：10.1016/s0957-4166(01)00088-x

  日期：2001.4

  1-(4'-Hydroxymethyl-phenyl)-2-methyl-3-(piperidine-1-yl)-propane-1-one M2, a metabolite of tolperisone, was synthesised in a solvent-free Mannich reaction. The optical resolution was carried out by diastereoisomeric salt formation and separation, for which three resolving agents ((2R,3R)-O,O'-dibenzoyl tartaric acid, (2R,3R)-O,O'-di-p-toluoyl tartaric acid and (R)-2-hydroxy-4-(2-methoxyphenyl)-5.5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide (anicyphos)) were found. The absolute configuration of M2 was determined by the single-crystal X-ray diffraction method. (C) 2001 Elsevier Science Ltd. All rights reserved.