(1E)-1,1-dichloro-2-(5-(3-methoxyphenyl)-2-penten-2-yl)-2-triisopropylsilyloxycyclopropane | 952315-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1E)-1,1-dichloro-2-(5-(3-methoxyphenyl)-2-penten-2-yl)-2-triisopropylsilyloxycyclopropane
• 英文别名: [2,2-dichloro-1-[(E)-5-(3-methoxyphenyl)pent-2-en-2-yl]cyclopropyl]oxy-tri(propan-2-yl)silane
• CAS: 952315-85-4
• 化学式: C₂₄H₃₈Cl₂O₂Si
• 分子量: 457.556
• InChiKey: UVCAOAXVHPRTDX-RGVLZGJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (1E)-1,1-dichloro-2-(5-(3-methoxyphenyl)-2-penten-2-yl)-2-triisopropylsilyloxycyclopropane 在 silver tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以89%的产率得到1-(N-benzyl-N-methylamino)-2-chloro-7-methoxy-9b-methyl-2,3,3a,4,5,9b-hexahydrocyclopenta[a]naphthalene
  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：

  ethyl (2E)-5-(3-methoxyphenyl)-2-methyl-2-pentenoate 在 sodium hydroxide 、 苄基三乙基氯化铵 、 二甲羟胺盐酸盐 、 二甲基氯化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 (1E)-1,1-dichloro-2-(5-(3-methoxyphenyl)-2-penten-2-yl)-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

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.