(2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazol-2(3H)-thione | 632330-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazol-2(3H)-thione
• 英文别名: [(2R,3S)-2-[(4-methyl-2-sulfanylidene-1,3-thiazol-3-yl)oxy]hex-5-en-3-yl] benzoate
• CAS: 632330-40-6
• 化学式: C₁₇H₁₉NO₃S₂
• 分子量: 349.475
• InChiKey: FEOBJULPZFSXKN-HIFRSBDPSA-N

物化性质

• 沸点：
  458.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazol-2(3H)-thione 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 1.42h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2R,3S,5S)-5-bromomethyl-2-methyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions

  摘要：

  A new synthesis of (-)-muscarine, (+)-allo-muscarine, (-)-epi-muscarine, and (-)-epiallo-muscarine has been devised which utilizes selective alkoxyl radical cyclizations for constructing tri-substituted tetrahydrofuran units. Photolysis of (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazole-2(3H)thione in the presence of BrCCl3 provided (2R,3S,5S)-3-benzoyloxy-5-broniomethyl-2-methyltetrahydrofuran as the major product and the corresponding (2R,3S,5R)-isomer as the minor. These building blocks were converted into enantiomerically pure (+)-allo-muscarine (from the major alkoxyl radical cyclization product) and (-)-muscarine (from the minor product). Temperature and substituent effects on the diastereoselectivity of the underlying alkoxyl radical cyclization have been investigated. (-)-epi-Muscarine and (-)-epiallo-muscarine have been prepared likewise, starting from (2R.3R)-ev-(3-benzoyloxy-5-hexen-2-oxy)-4-metliylthiazole-2(3H)thione. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2003.06.006
• 作为产物：
  描述：

  (2S)-3-benzoyloxy-2-(tetrahydropyran-2-yl)oxy-5-hexene 在 三乙烯二胺 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazol-2(3H)-thione
  参考文献：
  名称：

  Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions

  摘要：

  A new synthesis of (-)-muscarine, (+)-allo-muscarine, (-)-epi-muscarine, and (-)-epiallo-muscarine has been devised which utilizes selective alkoxyl radical cyclizations for constructing tri-substituted tetrahydrofuran units. Photolysis of (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazole-2(3H)thione in the presence of BrCCl3 provided (2R,3S,5S)-3-benzoyloxy-5-broniomethyl-2-methyltetrahydrofuran as the major product and the corresponding (2R,3S,5R)-isomer as the minor. These building blocks were converted into enantiomerically pure (+)-allo-muscarine (from the major alkoxyl radical cyclization product) and (-)-muscarine (from the minor product). Temperature and substituent effects on the diastereoselectivity of the underlying alkoxyl radical cyclization have been investigated. (-)-epi-Muscarine and (-)-epiallo-muscarine have been prepared likewise, starting from (2R.3R)-ev-(3-benzoyloxy-5-hexen-2-oxy)-4-metliylthiazole-2(3H)thione. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2003.06.006