α,α-Diphenylpropiophenone | 36504-01-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α,α-Diphenylpropiophenone
• 英文别名: 1,2,2-triphenylpropan-1-one；ω-Methyl-ω,ω-diphenyl-acetophenon；1,2,2-Triphenylpropanon；1,2,2-Triphenyl-propanon-(1)；1,1-Diphenylethylphenylketon；1,2,2-Triphenyl-propan-1-on；1,2,2-Triphenyl-1-propanone
• CAS: 36504-01-5
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: XGMJSKHYRPQWNT-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C
• 沸点：
  426.9±14.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  α,α-Diphenylpropiophenone 生成 9-甲基芴
  参考文献：
  名称：

  High intensity, argon ion laser-jet photochemistry

  摘要：

  DOI：

  10.1016/0584-8539(90)80169-y
• 作为产物：
  描述：

  2-benzoyl-2,5,6-triphenyl-3,4-dihydro-2H-pyran 在 三氯化铝 作用下， 生成 α,α-Diphenylpropiophenone
  参考文献：
  名称：

  Matti,J. et al., Bulletin de la Societe Chimique de France, 1963, p. 1176 - 1181

  摘要：

  DOI：

文献信息

• Acid-catalyzed reactions of 1,2-Dicarbonylethanes with benzene. Ethylene dication electrophiles
  作者：Takahisa Yamazaki、Shin-ichi Saito、Tomohiko Ohwada、Koichi Shudo

  DOI：10.1016/0040-4039(95)01075-s

  日期：1995.8

  1,2-Dicarbonyl compounds reacted with benzene in the presence of a strong acid, trifluoromethanesulfonic acid, to give gem-diphenylated ketones in high yields. The reaction was accelerated when the acidity of the medium was increased, supporting involvement of O,O-diprotonated 1,2-dicarbonyl species (i.e., 1,2-dihydroxyethylene dications) as the active electrophiles.

  1,2-二羰基化合物在强酸三氟甲磺酸的存在下与苯反应，以高收率得到了宝石-二苯基化的酮。当介质的酸度增加时，反应被加速，从而支持了O，O-二质子化的1,2-二羰基物质（即1,2-二羟基乙烯二羧酸）作为活性亲电子试剂的参与。
• The Chemistry of Hydroperoxides. IX. Relative Migratory Aptitudes of Groups in free Radical Rearrangements
  作者：M. S. Kharasch、Algirdas C. Poshkus、Andrew Fono、W. Nudenberg

  DOI：10.1021/jo50003a018

  日期：1951.9
• Some Observations on the Alkylation of Diphenylacetophenone and Diphenylacetone
  作者：Heinrich Rinderknecht

  DOI：10.1021/ja01156a082

  日期：1951.12
• Structures and Reactivities of Ethylene Dication Electrophiles
  作者：Tomohiko Ohwada、Takahisa Yamazaki、Takayoshi Suzuki、Shinichi Saito、Koichi Shudo

  DOI：10.1021/ja953623z

  日期：1996.1.1

  1,2-Dicarbonyl compounds such as 2,3-butanedione reacted with benzene in the presence of a strong acid, trifluoromethanesulfonic acid, to give gem-diphenylated ketones in high yield. The monoxime derivative of 1,2-diones also reacted with benzene in the acid, but slowly enough to allow discrimination of monophenylated and diphenylated oximes. The reactive electrophiles in these Friedel-Crafts reactions are considered to be O,O-diprotonated 1,2-dicarbonyl species and N,O-diprotonated ketoxime, i.e., related ethylene dications differentiated by a single different heteroatom substituent, a hydroxy or a hydroxyamino group. The reactivity depends on the electron-donating ability of substituents adjacent to the reaction center.
• Kulp, Stuart S.; Romanelli, Anthony, Organic Preparations and Procedures International, 1992, vol. 24, # 1, p. 7 - 12
  作者：Kulp, Stuart S.、Romanelli, Anthony

  DOI：——

  日期：——