2-(2,6-dimethylphenyl)-1-(naphthalen-1-yl)ethanone | 960591-78-0

• 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-(naphthalen-1-yl)ethanone
• 英文别名: 2-(2,6-dimethylphenyl)-1-(1-naphthalenyl)ethanone；2-(2,6-Dimethylphenyl)-1-(naphthalen-1-yl)ethan-1-one；2-(2,6-dimethylphenyl)-1-naphthalen-1-ylethanone
• CAS: 960591-78-0
• 化学式: C₂₀H₁₈O
• 分子量: 274.362
• InChiKey: UBMMBUXUDULRKO-UHFFFAOYSA-N

物化性质

• 沸点：
  448.2±14.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-萘乙酮 、 2-氯-1,3-二甲苯 在 (C₅H₅)Fe(C₅H₃C(CH₃)NC₆H₄CH₃)PdCl(CN₂(C₆H₃(CH(CH₃)2)2)2C₂H₂) 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以75%的产率得到2-(2,6-dimethylphenyl)-1-(naphthalen-1-yl)ethanone
  参考文献：
  名称：

  环palpalated二茂铁亚胺的碳烯加合物催化酮与芳基氯化物或溴化物的α-芳基化反应

  摘要：

  环palpalated二茂铁亚胺的碳烯加合物对酮与芳基卤化物的α-芳基化反应表现出很高的催化活性。以中等至优异的产率获得了相应的产物。该方案适用于各种酮类和广泛范围的芳基卤化物，包括芳基氯化物，溴化物以及未活化和空间受阻的芳基卤化物。

  DOI：

  10.1016/j.tet.2011.08.036

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.
• Carbene adduct of cyclopalladated ferrocenylimine catalyzed α-arylation of ketones with aryl chlorides or bromides
  作者：Jinli Zhang、Xueqian Yang、Xiuling Cui、Yangjie Wu

  DOI：10.1016/j.tet.2011.08.036

  日期：2011.11

  Carbene adduct of cyclopalladated ferrocenylimine exhibited highly catalytic activity for the α-arylation of ketones with aryl halides. The corresponding products were obtained in moderate to excellent yields. Such protocol was applied to various ketones and a broad scope of aryl halides including aryl chlorides, bromides as well as unactivated and sterically hindered aryl halides.

  环palpalated二茂铁亚胺的碳烯加合物对酮与芳基卤化物的α-芳基化反应表现出很高的催化活性。以中等至优异的产率获得了相应的产物。该方案适用于各种酮类和广泛范围的芳基卤化物，包括芳基氯化物，溴化物以及未活化和空间受阻的芳基卤化物。