(3S,4S)-1-Allyl-pyrrolidine-3,4-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4S)-1-Allyl-pyrrolidine-3,4-diol
• 英文别名: (3S,4S)-1-prop-2-enylpyrrolidine-3,4-diol
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: HRBXGVGYORAILE-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-Allyl-pyrrolidine-3,4-diol 、 alkaline earth salt of/the/ methylsulfuric acid 生成 Acetic acid (3R,4R)-4-acetoxy-1-allyl-pyrrolidin-3-yl ester
  参考文献：
  名称：

  Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration

  摘要：

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00791-7
• 作为产物：
  描述：

  Sulfuric acid mono-((3R,4R)-1-allyl-4-sulfooxy-pyrrolidin-3-yl) ester 在 硫酸 作用下， 生成 (3S,4S)-1-Allyl-pyrrolidine-3,4-diol
  参考文献：
  名称：

  Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration

  摘要：

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)00791-7

文献信息

• New Route to <i>N</i>‐Alkylated <i>trans</i>‐Pyrrolidine Diols from 2,2,3,3‐Tetramethoxybutane‐Protected Dimethyl Tartrate
  作者：J. Graça Martins、P. Cambeiro Barrulas、Carolina S. Marques、Anthony J. Burke

  DOI：10.1080/00397910801916520

  日期：2008.4

  Abstract A short synthesis of some trans‐pyrrolidine diols is described starting from (2R,3R,5R,6R)‐5,6‐dimethoxy‐5,6‐dimethyl[1,4]dioxane‐2,3‐dicarboxylic acid dimethyl ester 3. The key step was the occurrence of a tandem azide reduction/cyclization sequence on mono‐azide intermediate 6 upon catalytic hydrogenation. This method afforded both (3R,4R)‐(+)‐1‐benzyl‐3,4‐pyrrolidinediol 9a and (3R,4R)‐(+)‐1‐allyl‐3

  摘要 以 (2R,3R,5R,6R)-5,6-二甲氧基-5,6-二甲基[1,4]二恶烷-2,3-二甲酸二甲酯为原料，快速合成了一些反式吡咯烷二醇。 3. 关键步骤是单叠氮化物中间体 6 在催化氢化时发生串联叠氮化物还原/环化序列。该方法从 3 开始得到 (3R,4R)-(+)-1-苄基-3,4-吡咯烷二醇 9a 和 (3R,4R)-(+)-1-烯丙基-3,4-吡咯烷二醇 9b。使用盐水虾生物测定法对化合物 9a 和 9b 进行了测试，但每种都没有显示出活性，使用稳定的自由基二苯基苦基肼 (DPPH) 进行的抗氧化测试也是如此。