(5-methoxybiphenyl-2-yl)(phenyl)methanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (5-methoxybiphenyl-2-yl)(phenyl)methanone
• 英文别名: (4-methoxy-2-phenylphenyl)-phenylmethanone
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: XCRCHRBQFAYZAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  3’-甲氧基乙酰苯胺 在 叔丁基过氧化氢 、 三氟化硼甲醇络合物 、 palladium diacetate 、 sodium dodecyl sulfate 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 54.0h， 生成 (5-methoxybiphenyl-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions

  摘要：

  The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.

  DOI：

  10.1021/acs.joc.5b00272

文献信息

• The Barbier-Grignard-Type Arylation of Ketones and Unexpected Cross-Coupling of Phenolic Ketones using Unactivated Aryl Bromides
  作者：Yunming Wen、Guifang Chen、Shiqiang Huang、Yu Tang、Jun Yang、Yuanming Zhang

  DOI：10.1002/adsc.201500743

  日期：2016.3.17

  ketones and an unexpected cross‐coupling of phenolic ketones was observed using unactivated bromides and magnesium in tetrahydrofuran/toluene at 96 °C promoted by multicatalysts of cupric bromide (15 mol%), bismuth chloride (5 mol%) and silver bromide (10 mol%). The substituent and electronic effects on the reaction have been discussed. High yields of arylation and cross‐coupling have been attained under

  已开发出一种新颖，高度通用且高效的方法，用于酮的Barbier-Grignard型芳基化，并在96°C下使用未活化的溴化物和镁在四氢呋喃/甲苯中的未活化溴化物和镁在铜的多催化剂促进下观察到了酚酮的意外交叉偶联。溴化物（15摩尔％），氯化铋（5摩尔％）和溴化银（10摩尔％）。已经讨论了取代基和对反应的电子作用。在温和条件下，芳构化和交叉偶联的收率很高。提出了一种新颖的涉及醌中间体的合理机理。与酚酮的羟基交叉偶联的高化学选择性应有助于酮找到新的应用。
• Hattori, Tetsutaro; Takeda, Ayanobu; Suzuki, Kenji, Journal of the Chemical Society. Perkin transactions I, 1998, # 22, p. 3661 - 3671
  作者：Hattori, Tetsutaro、Takeda, Ayanobu、Suzuki, Kenji、Koike, Nobuyuki、Koshiishi, Eiji、Miyano, Sotaro

  DOI：——

  日期：——
• Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions
  作者：Bernd Schmidt、Nelli Elizarov、Uwe Schilde、Alexandra Kelling

  DOI：10.1021/acs.joc.5b00272

  日期：2015.5.1

  The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.