2,2-bis(3,4-dimethoxyphenyl)-1-phenylethanone | 27922-91-4

• 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: 2,2-bis(3,4-dimethoxyphenyl)-1-phenylethanone
• 英文别名: 2,2-Bis(3,4-dimethoxyphenyl)-1-phenylethan-1-one
• CAS: 27922-91-4
• 化学式: C₂₄H₂₄O₅
• 分子量: 392.452
• InChiKey: OZJGSKXLJMKYHK-UHFFFAOYSA-N

物化性质

• 沸点：
  533.0±50.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二苯基乙酮 、 邻苯二甲醚 在 dipotassium peroxodisulfate 、 三氟乙酸 作用下， 反应 24.0h， 以72%的产率得到2,2-bis(3,4-dimethoxyphenyl)-1-phenylethanone
  参考文献：
  名称：

  Aerobic Dehydrogenative α-Diarylation of Benzyl Ketones with Aromatics through Carbon–Carbon Bond Cleavage

  摘要：

  Substituted benzyl ketones reacted with aromatics in the presence of K2S2O8 in CF3COOH at room temperature, yielding alpha-diaryl benzyl ketones through a carbon-carbon bond cleavage. In the reaction, two new carbon-carbon bonds were formed and one carbon-carbon bond was cleaved. It is very interesting that two different nucleophiles such as benzyl ketones and aromatics were coupled together without metal, which is unusual in organic synthesis.

  DOI：

  10.1021/ol500079y

文献信息

• Palladium-Catalyzed Arylation of Ketone Enolates:  An Expeditious Entry to Tamoxifen-Related 1,2,2-Triarylethanones
  作者：Fátima Churruca、Raul SanMartin、Imanol Tellitu、Esther Domínguez

  DOI：10.1021/ol025811h

  日期：2002.5.1

  high yielding procedure for the preparation of 1,2,2-triarylethanones, skeletal analogues of tamoxifen, is presented. Apart from the economic and environmental advantages involved, this palladium-catalyzed arylation of deoxybenzoin enolates features a lack of ortho-arylation side reactions. In addition, an alternative approach from acetophenones to the target triarylethanone system is also announced

  [反应：请参见文字]。在对几种催化体系的作用进行了严格研究之后，提出了一种简单，高产的制备他莫昔芬骨架类似物1,2,2-triarylethanones的方法。除了所涉及的经济和环境优势外，这种钯催化的脱氧安息香烯醇烯酸酯的芳基化反应还缺少邻芳基化副反应。此外，还宣布了从苯乙酮到目标三芳酮系统的替代方法。
• Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading
  作者：Iratxe Astarloa、Raul SanMartin、María Teresa Herrero、Esther Domínguez

  DOI：10.1002/adsc.201701596

  日期：2018.4.17

  Acetophenone and deoxybenzoin derivatives are selectively α‐arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di‐ and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram‐scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic

  苯乙酮和脱氧安息香衍生物通过使用极少量的乙酸钯和二苯膦氧化物作为催化剂体系，而水作为唯一溶剂，选择性地进行α-芳基化。分离出的目标二-和三芳基酮几乎不含金属残留物，反应量可达到克级。还提供了基于TEM图像，中毒实验，动力学图和ESI-MS光谱的机械方案。
• Regioselective diarylation of ketone enolates by homogeneous and heterogeneous catalysis: synthesis of triarylethanones
  作者：Fátima Churruca、Raul SanMartin、Imanol Tellitu、Esther Domı́nguez

  DOI：10.1016/s0040-4039(03)01398-4

  日期：2003.7

  A novel, one-step approach to 1,2,2-triarylethanones is achieved by an efficient palladium-catalyzed alpha,alpha-diarylation of commercially available acetophenones. After assaying an array of experimental conditions, two convenient procedures, which avoid ortho-arylation side reactions, are chosen to perform the target regioselective diarylation. The former protocol is based on the use of such a simple homogeneous system as Pd(OAc)(2)/PPh3/Cs2CO3, and the latter one employs a commercially available polymer-anchored catalyst. FibreCat(TM) 1026. (C) 2003 Elsevier Ltd. All rights reserved.
• Towards a facile synthesis of triarylethanones: palladium-catalyzed arylation of ketone enolates under homogeneous and heterogeneous conditions
  作者：Fátima Churruca、Raul SanMartin、Mónica Carril、Imanol Tellitu、Esther Domı́nguez

  DOI：10.1016/j.tet.2003.12.065

  日期：2004.3

  The palladium-catalyzed regioselective alpha-monoarylation of deoxybenzoins and alpha,alpha-diarylation of acetophenones provides general, efficient access to 1,2,2-triarylethanones. After a comprehensive search for suitable experimental conditions to optimize such transformations, both reactions are alternatively conducted by means of either commercially available polymer-anchored catalysts or a very simple homogeneous catalytic system, thus avoiding the use of complex ligands. In addition, the synthesis of deoxybenzoins employing polymer-supported fibrous palladium catalysts is reported for the first time, and the excellent catalyst recycling properties suggest applicability to industrial purposes. (C) 2004 Elsevier Ltd. All rights reserved.
• Aerobic Dehydrogenative α-Diarylation of Benzyl Ketones with Aromatics through Carbon–Carbon Bond Cleavage
  作者：Nagnath Yadav More、Masilamani Jeganmohan

  DOI：10.1021/ol500079y

  日期：2014.2.7

  Substituted benzyl ketones reacted with aromatics in the presence of K2S2O8 in CF3COOH at room temperature, yielding alpha-diaryl benzyl ketones through a carbon-carbon bond cleavage. In the reaction, two new carbon-carbon bonds were formed and one carbon-carbon bond was cleaved. It is very interesting that two different nucleophiles such as benzyl ketones and aromatics were coupled together without metal, which is unusual in organic synthesis.