(E)-6-[tert-butyl(dimethyl)silyl]oxy-2-diethoxyphosphorylhex-4-enenitrile | 656232-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (E)-6-[tert-butyl(dimethyl)silyl]oxy-2-diethoxyphosphorylhex-4-enenitrile
• CAS: 656232-76-7
• 化学式: C₁₆H₃₂NO₄PSi
• 分子量: 361.494
• InChiKey: JMRGDLFEXRRTKN-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-6-[tert-butyl(dimethyl)silyl]oxy-2-diethoxyphosphorylhex-4-enenitrile 在 四(三苯基膦)钯 potassium hexamethyldisilazane 、 六甲基二锡 、 N,N-二异丙基乙胺 作用下， 以 甲苯 、 苯 为溶剂， 反应 22.0h， 生成 (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：

  氰甲基磷酸二乙酯 、 (E)-4-<(tert-Butyldimethylsilyl)oxy>-2-buten-1-ol mesylate 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.75h， 以62%的产率得到(E)-6-[tert-butyl(dimethyl)silyl]oxy-2-diethoxyphosphorylhex-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+

文献信息

• “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
  作者：Kathlyn A. Parker、Yeon-Hee Lim

  DOI：10.1021/ol036048+

  日期：2004.1.1

  [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.