2-(2,6-dimethylphenyl)-1-(3-methoxyphenyl)ethanone | 960591-80-4

• 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-(2,6-dimethylphenyl)-1-(3-methoxyphenyl)ethanone
• 英文别名: 2-(2,6-Dimethylphenyl)-1-(3-methoxyphenyl)ethanone
• CAS: 960591-80-4
• 化学式: C₁₇H₁₈O₂
• mdl: MFCD25250334
• 分子量: 254.329
• InChiKey: VJCMIZVKAUREKM-UHFFFAOYSA-N

物化性质

• 沸点：
  390.2±32.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 3-甲氧基苯乙酮 在 [Pd(IHept)(acac)Cl] 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以92%的产率得到2-(2,6-dimethylphenyl)-1-(3-methoxyphenyl)ethanone
  参考文献：
  名称：

  低催化剂负载下钯催化的芳酮的α-芳基化

  摘要：

  已经开发出用于芳基酮α-芳基化的一般催化方案。它涉及使用预成型的，板凳稳定的Pd– N杂环卡宾预催化剂作为辅助配体，并允许在非常低的催化剂负载量下偶联各种官能化的偶联伙伴。仔细选择溶剂/碱体系对于获得最佳催化剂性能至关重要。在合成工业上有用的化合物时，也成功地测试了前催化剂。

  DOI：

  10.1002/chem.201404900

文献信息

• A Highly Practical and General Route for α-Arylations of Ketones Using Bis-phosphinoferrocene-Based Palladium Catalysts
  作者：Gabriela A. Grasa、Thomas J. Colacot

  DOI：10.1021/op7002503

  日期：2008.5.1

  Well-defined, air-stable Pd complexes of bis-phosphinoferrocene family of catalysts have been studied in the arylation of various ketones with aryl chlorides and aryl bromides. Bis(di-tert-butyl)phosphinoferrocene (DtBPF)-based catalysts such as (DtBPF) PdCl2 and (DtBPF)PdBr2 have been identified as two of the most active catalysts for the alpha-arylation of a model reaction involving propiophenone and 4-chlorotoluene. The scope of the (DtBPF)PdCl2 catalyst has been efficiently expanded to the arylation of various ketones with aryl chlorides and bromides with up to 97% isolated yields, under relatively mild reaction conditions at low catalyst loadings. The efficacy of the (DtBPF)PdCl2 catalyst was demonstrated at very low catalyst loadings with SIC 10,000 for the difficult aryl bromide, 4-bromoanisole, and 2000 for the electron-neutral aryl chloride, 4-chlorotoluene, on similar to 10-g scale with excellent isolated yields and lower Pd in the product (6 and 48 ppm, respectively). Comparative studies on the Pd:DtBPF molar ratios between in situ catalysts and preisolated catalysts revealed that preisolated (DtBPF)PdX2 (X = Cl, Br) are the catalysts of choice due to various practical reasons.
• α-Arylation of Ketones Using Highly Active, Air-Stable (DtBPF)PdX₂ (X = Cl, Br) Catalysts
  作者：Gabriela A. Grasa、Thomas J. Colacot

  DOI：10.1021/ol702430a

  日期：2007.12.1

  alpha-Arylation of various ketones with aryl chlorides and bromides using the well-defined and air-stable (DtBPF)PdX2 (X = Cl, Br) catalysts gave 80-100% yield of the coupled products under relatively mild conditions at low catalyst loadings. The X-ray structure of (DtBPF)PdCl2 revealed the largest P-Pd-P bite angle (104.2 degrees) for a ferrocenyl bisphosphine ligand. P-31 NMR monitoring of (DtBPF)PdCl2-catalyzed reaction of 4-chlorotoluene with propiophenone indicated that DtBPF remained coordinated in a bidentate mode during the catalytic cycle.
• Palladium-Catalyzed α-Arylation of Arylketones at Low Catalyst Loadings
  作者：Enrico Marelli、Martin Corpet、Sian R. Davies、Steven P. Nolan

  DOI：10.1002/chem.201404900

  日期：2014.12.22

  involves the use of a preformed, bench‐stable Pd–N‐heterocyclic carbene pre‐catalyst bearing IHept as an ancillary ligand, and allows the coupling of various functionalized coupling partners at very low catalyst loading. Careful choice of the solvent/base system was crucial to obtain optimum catalyst performance. The pre‐catalyst was also successfully tested in the synthesis of an industrially relevant

  已经开发出用于芳基酮α-芳基化的一般催化方案。它涉及使用预成型的，板凳稳定的Pd– N杂环卡宾预催化剂作为辅助配体，并允许在非常低的催化剂负载量下偶联各种官能化的偶联伙伴。仔细选择溶剂/碱体系对于获得最佳催化剂性能至关重要。在合成工业上有用的化合物时，也成功地测试了前催化剂。