methyl (R,2Z,8E)-6-aza-10-hydroxy-5-isopropyl-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-2,8-dienoate | 1254356-75-6

• 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: methyl (R,2Z,8E)-6-aza-10-hydroxy-5-isopropyl-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-2,8-dienoate
• CAS: 1254356-75-6
• 化学式: C₂₆H₄₃NO₅SSi
• 分子量: 509.783
• InChiKey: OBLYMJLLBBXLCV-BCJVKQSFSA-N

物化性质

• 沸点：
  599.8±60.0 °C(predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (R,2Z,8E)-6-aza-10-hydroxy-5-isopropyl-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-2,8-dienoate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75%的产率得到methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-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：

  (E)-1-acetoxy-4-chloro-2-[(triethyl)silyl]but-2-ene 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 18.75h， 生成 methyl (R,2Z,8E)-6-aza-10-hydroxy-5-isopropyl-6-(p-toluenesulfonyl)-9-[(triethyl)silyl]deca-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