Bicyclo<5.1.1>nonan-4-one | 145325-96-8

• 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
• 英文别名: Bicyclo[5.1.1]nonan-4-one
• CAS: 145325-96-8
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: RRSQWWQPOQCYFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Bicyclo<5.1.1>nonan-4-one 在 硫酸 、 potassium tert-butylate 、 溴 、 对甲苯磺酸 作用下， 以 乙二醇 、 二甲基亚砜 、 苯 为溶剂， 反应 0.08h， 生成 <4,5>dihomotropone
  参考文献：
  名称：

  Synthesis and properties of [4,5]dihomotropone (bicyclo[5.1.1]Nona-2,5-dien-4-one)

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60984-x
• 作为产物：
  描述：

  4-Oxo-bicyclo[5.1.1]nonane-3-carboxylic acid ethyl ester 在 盐酸 作用下， 以 丙酮 为溶剂， 以82%的产率得到Bicyclo<5.1.1>nonan-4-one
  参考文献：
  名称：

  Synthesis and properties of [4,5]dihomotropone (bicyclo[5.1.1]Nona-2,5-dien-4-one)

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60984-x

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.