Bicyclo<5.1.1>nonane-3,5-dione | 166803-18-5

• 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>nonane-3,5-dione
• 英文别名: Bicyclo[5.1.1]nonane-3,5-dione
• CAS: 166803-18-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: PADGCVGDQHDXEP-UHFFFAOYSA-N

物化性质

• 沸点：
  290.5±13.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  s,s'-三甲烯(p-甲苯硫代磺酸盐) 、 Bicyclo<5.1.1>nonane-3,5-dione 在 potassium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以90%的产率得到Bicyclo<5.1.1>nonane-3,4,5-trione 4-(propylene dithioketal)
  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：

  3,4-Bis(trimethylsiloxy)bicyclo<4.1.1>oct-3-en 在 diethylzinc 、 三氯化铁 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 Bicyclo<5.1.1>nonane-3,5-dione
  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

• Is Through-Bond Dihydroaromaticity Attainable? Preparation of [4,5]Dihomotropone, Investigation of Its Ground-State Properties, and an Attempt to Generate the Dihomotropylium Cation
  作者：Leo A. Paquette、Timothy J. Watson、Dirk Friedrich、Roger Bishop、Eric Bacque

  DOI：10.1021/jo00098a031

  日期：1994.9

  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.