Bicyclo<5.1.1>nonan-4-one ethylene ketal | 146258-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bicyclo<5.1.1>nonan-4-one ethylene ketal
• 英文别名: Spiro[1,3-dioxolane-2,4'-bicyclo[5.1.1]nonane]
• CAS: 146258-62-0
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: LNJPJBFDVSXEHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  Bicyclo<5.1.1>nonan-4-one ethylene ketal 在 溴 作用下， 以 乙二醇 为溶剂， 反应 0.33h， 以82%的产率得到
  参考文献：
  名称：

  Is Through-Bond Dihydroaromaticity Attainable? Preparation of [4,5]Dihomotropone, Investigation of Its Ground-State Properties, and an Attempt to Generate the Dihomotropylium Cation

  摘要：

  Construction of the first dihomotropone (6) has been accomplished. The key elements of the synthesis were a regiocontrolled expansion of a [4.1.1] bicyclic cr-bromo ketone and introduction of the dienone double bonds by means of the Garbisch method. The spectral properties of 6 under neutral and strongly acidic conditions are described and interpreted in terms of a lack of dihomoaromatic character. The parent bicyclo[5.1.1]nonadienyl cation is unstable and experiences ready Wagner-Meerwein rearrangement to the bicyclo[4.2.1]nonadien-7-yl cation. These features appear well suited to the ultimate evaluation of through-bond interaction in tricyclic homologues of 6 that carry perpendicular pi arrays in the third ring.

  DOI：

  10.1021/jo00098a031
• 作为产物：
  描述：

  4-Hydroxy-bicyclo[4.1.1]octan-3-one 在 吡啶 、 盐酸 、 三氟化硼乙醚 、 对甲苯磺酸 、 溶剂黄146 、 lithium bromide 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 108.5h， 生成 Bicyclo<5.1.1>nonan-4-one ethylene ketal
  参考文献：
  名称：

  Is Through-Bond Dihydroaromaticity Attainable? Preparation of [4,5]Dihomotropone, Investigation of Its Ground-State Properties, and an Attempt to Generate the Dihomotropylium Cation

  摘要：

  Construction of the first dihomotropone (6) has been accomplished. The key elements of the synthesis were a regiocontrolled expansion of a [4.1.1] bicyclic cr-bromo ketone and introduction of the dienone double bonds by means of the Garbisch method. The spectral properties of 6 under neutral and strongly acidic conditions are described and interpreted in terms of a lack of dihomoaromatic character. The parent bicyclo[5.1.1]nonadienyl cation is unstable and experiences ready Wagner-Meerwein rearrangement to the bicyclo[4.2.1]nonadien-7-yl cation. These features appear well suited to the ultimate evaluation of through-bond interaction in tricyclic homologues of 6 that carry perpendicular pi arrays in the third ring.

  DOI：

  10.1021/jo00098a031

文献信息

• Synthesis and properties of [4,5]dihomotropone (bicyclo[5.1.1]Nona-2,5-dien-4-one)
  作者：Loe A. Paquette、Eric Bacqué、Roger Bishop、Timothy J. Watson

  DOI：10.1016/s0040-4039(00)60984-x

  日期：1992.10

  The potentially through-bond "dihomoaromatic" title compound has been elaborated by means of a tandem acyloin-ring expansion sequence and shown by spectroscopic means not to possess significant ground-state polarization.