methyl (5R,Z)-6-aza-5-benzyl-8-hydroxy-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate | 1254356-15-4

• 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: methyl (5R,Z)-6-aza-5-benzyl-8-hydroxy-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate
• 英文别名: methyl (Z,5R)-5-[(2-hydroxy-2-phenylethyl)-(4-methylphenyl)sulfonylamino]-6-phenylhex-2-enoate
• CAS: 1254356-15-4
• 化学式: C₂₈H₃₁NO₅S
• 分子量: 493.624
• InChiKey: LJRBEPVZYOBDHA-DWRDYKDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (5R,Z)-6-aza-5-benzyl-8-hydroxy-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate
  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：

  (S)-3-tosylamino-4-phenylbutanenitrile 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 23.75h， 生成 methyl (5R,Z)-6-aza-5-benzyl-8-hydroxy-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate
  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