(2S,3R)-3-benzoyloxy-5-hexen-2-ol | 285555-85-3

• 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: (2S,3R)-3-benzoyloxy-5-hexen-2-ol
• 英文别名: [(2S,3R)-2-hydroxyhex-5-en-3-yl] benzoate
• CAS: 285555-85-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: PYBQLLNSKXPRNP-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-benzoyloxy-5-hexen-2-ol 在 三乙烯二胺 、 三氯溴甲烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 120.42h， 生成 (2R,3R,5R)-3-benzoyloxy-5-bromomethyl-2-methyltetrahydrofuran
  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)-2-(四氢-2H-吡喃-2-基氧基)-5-己烯-3-醇 在 三乙烯二胺 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (2S,3R)-3-benzoyloxy-5-hexen-2-ol
  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

文献信息

• Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions
  作者：Jens Hartung、Rainer Kneuer

  DOI：10.1016/j.tetasy.2003.06.006

  日期：2003.10

  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.