(S,Z)-4-aza-3-methyl-4-(p-toluenesulfonyl)-8-(benzoyloxy)oct-6-enenitrile | 1254356-17-6

• 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: (S,Z)-4-aza-3-methyl-4-(p-toluenesulfonyl)-8-(benzoyloxy)oct-6-enenitrile
• 英文别名: [(Z)-4-[[(2S)-1-cyanopropan-2-yl]-(4-methylphenyl)sulfonylamino]but-2-enyl] benzoate
• CAS: 1254356-17-6
• 化学式: C₂₂H₂₄N₂O₄S
• 分子量: 412.51
• InChiKey: SUEKQCASQOHXDW-RURPWVQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S,Z)-4-aza-3-methyl-4-(p-toluenesulfonyl)-8-(benzoyloxy)oct-6-enenitrile 在 甲醇 、 sodium methylate 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.25h， 生成 methyl (5S,2Z,8Z)-6-aza-5-methyl-6-(p-toluenesulfonyl)-10-[(tertbutyldimethylsilyl)oxy]dec-2,8-dienoate
  参考文献：
  名称：

  Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical Cyclization

  摘要：

  A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto alpha,beta-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2 to 40:1 when the radical stabilizing group is vinyl or phenyl. Cyclization of a (triethylsilyl)vinyl-stabilized radical gives the corresponding piperidine radical as a single diastereoisomer that may either be trapped by tributyltin hydride to afford the 2,4,5-trisubstituted piperidine or undergo a second 5-endo cyclization onto the (triethylsilyl)vinyl substituent to produce the 3,5,7-trisubstituted octahydro[2]pyrindene as a single diastereoisomer.

  DOI：

  10.1021/jo101631y
• 作为产物：
  描述：

  4‐hydroxybut‐2‐en‐1‐yl benzoate 在 四溴化碳 、 caesium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.5h， 生成 (S,Z)-4-aza-3-methyl-4-(p-toluenesulfonyl)-8-(benzoyloxy)oct-6-enenitrile
  参考文献：
  名称：

  Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical Cyclization

  摘要：

  A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto alpha,beta-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2 to 40:1 when the radical stabilizing group is vinyl or phenyl. Cyclization of a (triethylsilyl)vinyl-stabilized radical gives the corresponding piperidine radical as a single diastereoisomer that may either be trapped by tributyltin hydride to afford the 2,4,5-trisubstituted piperidine or undergo a second 5-endo cyclization onto the (triethylsilyl)vinyl substituent to produce the 3,5,7-trisubstituted octahydro[2]pyrindene as a single diastereoisomer.

  DOI：

  10.1021/jo101631y