6-methyl-2,3,4,5-tetrahydro-cyclopenta[a]naphthalen-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methyl-2,3,4,5-tetrahydro-cyclopenta[a]naphthalen-1-one
• 英文别名: 6-Methyl-2,3,4,5-tetrahydrocyclopenta[a]naphthalen-1-one；6-methyl-2,3,4,5-tetrahydrocyclopenta[a]naphthalen-1-one
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: AMBXSFYMNYAXRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1E)-1,1-dichloro-2-(4-(2-methylphenyl)-1-butenyl)-2-triisopropylsilyloxycyclopropane 在 silver tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以79%的产率得到6-methyl-2,3,4,5-tetrahydro-cyclopenta[a]naphthalen-1-one
  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.