(E,2Z)-6-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-3-iodo-2-methylprop-2-enylidene]hex-4-enenitrile | 656232-73-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E,2Z)-6-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-3-iodo-2-methylprop-2-enylidene]hex-4-enenitrile
• CAS: 656232-73-4
• 化学式: C₁₆H₂₆INOSi
• 分子量: 403.379
• InChiKey: OFJFXYGIOBXAQG-BESMLHRRSA-N

物化性质

• 沸点：
  417.3±45.0 °C(predicted)
• 密度：
  1.231±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene 、 (E,2Z)-6-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-3-iodo-2-methylprop-2-enylidene]hex-4-enenitrile 在 四(三苯基膦)钯 、 双(乙腈)氯化钯(II) 六甲基二锡 、 N,N-二异丙基乙胺 作用下， 以 苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以83.5 mg的产率得到(1S,6S,7R,8R)-7-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyl]-1,3,5-trimethyl-8-(4-nitro-phenyl)-bicyclo[4.2.0]octa-2,4-diene-7-carbonitrile
  参考文献：
  名称：

  “Endo” and “Exo” Bicyclo[4.2.0]-octadiene Isomers from the Electrocyclization of Fully Substituted Tetraene Models for SNF 4435C and D. Control of Stereochemistry by Choice of a Functionalized Substituent

  摘要：

  [GRAPHICS]A tandem electrocyclic closure, perceived as the key step in a biomimetic approach to SNF 4435C and D, was tested with 1,1,8-trisubstituted tetraene substrates. The ratio of endo:exo products could be controlled by the choice of the R-z substituent at C-1. On the basis of these results, a short stereoselective route to an advanced SNF 4435 intermediate was devised.

  DOI：

  10.1021/ol036048+
• 作为产物：
  描述：

  (E)-4-<(tert-Butyldimethylsilyl)oxy>-2-buten-1-ol mesylate 在 potassium hexamethyldisilazane 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 30.75h， 生成 (E,2Z)-6-[tert-butyl(dimethyl)silyl]oxy-2-[(Z)-3-iodo-2-methylprop-2-enylidene]hex-4-enenitrile
  参考文献：
  名称：

  “Endo” and “Exo” Bicyclo[4.2.0]-octadiene Isomers from the Electrocyclization of Fully Substituted Tetraene Models for SNF 4435C and D. Control of Stereochemistry by Choice of a Functionalized Substituent

  摘要：

  [GRAPHICS]A tandem electrocyclic closure, perceived as the key step in a biomimetic approach to SNF 4435C and D, was tested with 1,1,8-trisubstituted tetraene substrates. The ratio of endo:exo products could be controlled by the choice of the R-z substituent at C-1. On the basis of these results, a short stereoselective route to an advanced SNF 4435 intermediate was devised.

  DOI：

  10.1021/ol036048+