α,α-dibenzylcyclohexanone | 7382-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α,α-dibenzylcyclohexanone
• 英文别名: 2,2-Dibenzylcyclohexanone；2,2-dibenzyl-cyclohexanone；2,2-Dibenzyl-cyclohexanon；α,α-Dibenzyl-cyclohexanon；1,1-Dibenzyl-cyclohexanon-(2)；2,2-Dibenzylcyclohexan-1-one
• CAS: 7382-11-8
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: CYUTWCRUZBMGCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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-dibenzylcyclohexanone 在 盐酸 、 甲基锂 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 20.5h， 生成 3,3-Dibenzylcyclohexene
  参考文献：
  名称：

  Cyclization and rearrangement processes resulting from bromination of 3-benzylcycloalkenes

  摘要：

  DOI：

  10.1021/jo00062a043
• 作为产物：
  描述：

  环己酮 、 溴甲苯 在 sodium tert-pentoxide 作用下， 生成 α,α-dibenzylcyclohexanone
  参考文献：
  名称：

  Chemistry of carbanions. XIX. Alkylation of enolates from unsymmetrical ketones

  摘要：

  DOI：

  10.1021/jo00815a037

文献信息

• Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters
  作者：Martin���R. Albicker、Nicolai Cramer

  DOI：10.1002/anie.200905060

  日期：2009.11.16

  Ta daa: The title reaction proceeds under essentially neutral reaction conditions at ambient temperature with a taddol‐based phosphoramidite ligand L* allowing the creation of indanes with quaternary stereogenic centers in high enantiomeric excess (see scheme; Tf=trifluoromethanesulfonyl, DMAc=dimethylacetamide).

  Ta daa：标题反应在室温下基本基于中性反应条件下，使用基于taddol的亚磷酰胺配体L *进行，从而以对映体过量的形式生成具有季立体异构中心的茚满（见方案; Tf =三氟甲磺酰基，DMAc =二甲基乙酰胺）。
• The preparation and reaction of enolates within micro reactors
  作者：Charlotte Wiles、Paul Watts、Stephen J. Haswell、Esteban Pombo-Villar

  DOI：10.1016/j.tet.2005.08.076

  日期：2005.11

  Over the past 5 years, interest in the miniaturisation of chemical synthesis has grown rapidly, however in order to facilitate transfer of the technology from its current position as a research tool to industrial applications, a core understanding of the challenges associated with transferring reactions from the macro to the micro domain is required. This paper therefore aims to broach this problem by investigating the application of micro reactors to a range of commonly employed synthetic reactions including acylation, aldol, alkylation, 1,4-conjugate addition (Michael addition) and the Knoevenagel condensation. Comparison of the results obtained with traditional batch techniques enable us to highlight some of the advantages associated with micro reaction technology. (c) 2005 Elsevier Ltd. All rights reserved.
• Alkylation of enolates with triflates
  作者：Robert B. Bates、Stuart R. Taylor

  DOI：10.1021/jo00068a050

  日期：1993.7
• Alkylation of Carbonyl Compounds in Water: Formation of CC and CO Bonds in the Presence of Surfactants
  作者：Giorgio Cerichelli、Simona Cerritelli、Marco Chiarini、Paolo De Maria、Antonella Fontana

  DOI：10.1002/1521-3765(20021115)8:22<5204::aid-chem5204>3.0.co;2-c

  日期：2002.11.15

  The formation of C-C and C-O bonds by the reaction of enolate intermediates with electrophilic substrates commonly requires strong bases, aprotic solvents and very low temperatures. A way of performing the same reactions with sodium hydroxide at moderate temperatures in aqueous surfactant solutions is presented. Different halides, ketones and surfactants (cationic, zwitterionic and anionic) have been used. The results obtained show that the amount of ketone alkylation is much higher and that the reactions are faster in the presence than in the absence of surfactant aggregates. The hydrolysis of the halide is minimised in the presence of cationic or zwitterionic surfactants.
• Enantioselective addition of lithium trimethylsilyl acetylide to substituted cyclohexanones synthesis of optically active tertiary cyclohexanols
  作者：Katja Scharpwinkel、Stefan Matull、Hans J. Schäfer

  DOI：10.1016/0957-4166(96)00316-3

  日期：1996.9

  Optically active tertiary alkynyl cyclohexanols were obtained by enantioselective addition of lithium trimethylsilylacetylide to cyclohexanones with different substituents in the alpha- and the beta-position. (2S,2'S)-2-Hydroxymethyl-1-[(1-methylpyrrolidin-2-yl)methyl]pyrrolidine 2 proved to be an effective chiral ligand for the addition. Copyright (C) 1996 Elsevier Science Ltd