14-oxatetracyclo[6.6.0.01,13.02,7]tetradeca-2,4,6-triene | 55386-31-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 14-oxatetracyclo[6.6.0.01,13.02,7]tetradeca-2,4,6-triene
• CAS: 55386-31-7
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: GKPMUKIHIKGTKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  14-oxatetracyclo[6.6.0.01,13.02,7]tetradeca-2,4,6-triene 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以58%的产率得到7,8-benzobicyclo<4.2.1>7-nonen-9-one
  参考文献：
  名称：

  Bridged aromatic alkenes for the study of carbocation–π interaction

  摘要：

  Toward the goal of gaining further insight into carbocation-pi interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit pi complexation of an intramolecular tertiary carbocation with a benzene ring, but the other isomer will not. The syntheses of three sets of such isomers, having, respectively, benzobicyclo[3.21]octene, benzobicyclo[2.2.1]heptene, and benzobicyclo[4.2.1]nonene structures, are described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.029
• 作为产物：
  描述：

  8,9-Benzobicyclo-<5.2.0>nona-1,8-dien 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到14-oxatetracyclo[6.6.0.01,13.02,7]tetradeca-2,4,6-triene
  参考文献：
  名称：

  Bridged aromatic alkenes for the study of carbocation–π interaction

  摘要：

  Toward the goal of gaining further insight into carbocation-pi interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit pi complexation of an intramolecular tertiary carbocation with a benzene ring, but the other isomer will not. The syntheses of three sets of such isomers, having, respectively, benzobicyclo[3.21]octene, benzobicyclo[2.2.1]heptene, and benzobicyclo[4.2.1]nonene structures, are described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.029

文献信息

• Bridged aromatic alkenes for the study of carbocation–π interaction
  作者：Thomas A. Spencer、Janeta Popovici-Müller、Bobbijo van Beusichem、Celeste Viscardi MacMillan、Carolee F. Lavey、Jessica M. Sin、Robert Ditchfield

  DOI：10.1016/j.tet.2010.04.029

  日期：2010.6

  Toward the goal of gaining further insight into carbocation-pi interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit pi complexation of an intramolecular tertiary carbocation with a benzene ring, but the other isomer will not. The syntheses of three sets of such isomers, having, respectively, benzobicyclo[3.21]octene, benzobicyclo[2.2.1]heptene, and benzobicyclo[4.2.1]nonene structures, are described. (C) 2010 Elsevier Ltd. All rights reserved.