Methanesulfonic acid 4-oxo-bicyclo[4.1.1]oct-3-yl ester | 145325-90-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid 4-oxo-bicyclo[4.1.1]oct-3-yl ester
• 英文别名: 4-[(Methylsulfonyl)oxy]bicyclo[4.1.1]octan-3-one；(4-oxo-3-bicyclo[4.1.1]octanyl) methanesulfonate
• CAS: 145325-90-2
• 化学式: C₉H₁₄O₄S
• 分子量: 218.274
• InChiKey: QLXOJJHQCWFRLX-UHFFFAOYSA-N

物化性质

• 沸点：
  401.0±24.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid 4-oxo-bicyclo[4.1.1]oct-3-yl ester 在 lithium bromide 作用下， 以 丙酮 为溶剂， 以61%的产率得到4-Bromobicyclo<4.1.1>octan-3-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
• 作为产物：
  描述：

  4-Hydroxy-bicyclo[4.1.1]octan-3-one 、 甲基磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以64%的产率得到Methanesulfonic acid 4-oxo-bicyclo[4.1.1]oct-3-yl ester
  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