(3E)-2-triisopropylsiloxy-6-(3-methoxyphenyl)-1,3-hexadiene | 952315-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3E)-2-triisopropylsiloxy-6-(3-methoxyphenyl)-1,3-hexadiene
• 英文别名: [(3E)-6-(3-methoxyphenyl)hexa-1,3-dien-2-yl]oxy-tri(propan-2-yl)silane
• CAS: 952315-64-9
• 化学式: C₂₂H₃₆O₂Si
• 分子量: 360.612
• InChiKey: DDXTWUAFNFCULK-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E)-2-triisopropylsiloxy-6-(3-methoxyphenyl)-1,3-hexadiene 、 氯仿 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 0.5h， 以75%的产率得到(1E)-1,1-dichloro-2-(4-(3-methoxyphenyl)-1-butenyl)-2-triisopropylsilyloxycyclopropane
  参考文献：
  名称：

  Interrupted Nazarov Reactions Using Dichlorocyclopropanes:  A Novel Mode of Arene Trapping

  摘要：

  2-Siloxy-2-alkenyl-1,1-dichlorocyclopropanes with aryl-terminated side chains undergo silver-assisted electrocyclic opening/Nazarov cyclization. The resulting 2-siloxycyclopentenyl cations are intercepted by the pendant arenes to furnish tricyclic adducts in moderate to good yields. In cases where the arene trap was tethered through the cyclopropane unit, a new mode of trapping occurred to generate unique bridged carbon frameworks.

  DOI：

  10.1021/ol7015669
• 作为产物：
  描述：

  3-(3-甲氧基苯基)-1-丙醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 (3E)-2-triisopropylsiloxy-6-(3-methoxyphenyl)-1,3-hexadiene
  参考文献：
  名称：

  Interrupted Nazarov Reactions Using Dichlorocyclopropanes:  A Novel Mode of Arene Trapping

  摘要：

  2-Siloxy-2-alkenyl-1,1-dichlorocyclopropanes with aryl-terminated side chains undergo silver-assisted electrocyclic opening/Nazarov cyclization. The resulting 2-siloxycyclopentenyl cations are intercepted by the pendant arenes to furnish tricyclic adducts in moderate to good yields. In cases where the arene trap was tethered through the cyclopropane unit, a new mode of trapping occurred to generate unique bridged carbon frameworks.

  DOI：

  10.1021/ol7015669

文献信息

• Interrupted Nazarov Reactions Using Dichlorocyclopropanes:  A Novel Mode of Arene Trapping
  作者：Tina N. Grant、F. G. West

  DOI：10.1021/ol7015669

  日期：2007.9.1

  2-Siloxy-2-alkenyl-1,1-dichlorocyclopropanes with aryl-terminated side chains undergo silver-assisted electrocyclic opening/Nazarov cyclization. The resulting 2-siloxycyclopentenyl cations are intercepted by the pendant arenes to furnish tricyclic adducts in moderate to good yields. In cases where the arene trap was tethered through the cyclopropane unit, a new mode of trapping occurred to generate unique bridged carbon frameworks.