1-[2'-(4,5-dihydro-1,3-oxazol-2-yl)-3'-methyl-biphenyl-4-yl]-ethanone | 851513-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2'-(4,5-dihydro-1,3-oxazol-2-yl)-3'-methyl-biphenyl-4-yl]-ethanone
• 英文别名: 1-(2'-(4,5-dihydrooxazol-2-yl)-3'-methylbiphenyl-4-yl)ethanone；1-{2'-(4,5-dihydrooxazol-2-yl)-3'-methyl-[1,1'-biphenyl]-4-yl}ethan-1-one；4-acetyl-3'-methyl-2'-(4,5-dihydrooxazol-2-yl)biphenyl；1-[4-[2-(4,5-Dihydro-1,3-oxazol-2-yl)-3-methylphenyl]phenyl]ethanone
• CAS: 851513-91-2
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: SAWWVUZGYNEEAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  87.6-88.4 °C
• 沸点：
  452.7±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2'-(4,5-dihydro-1,3-oxazol-2-yl)-3'-methyl-biphenyl-4-yl]-ethanone 、 三乙基硅烷 以 N-甲基吡咯烷酮 为溶剂， 反应 22.0h， 以172 mg的产率得到2-[3-methyl-4'-(1-triethylsilanyloxyethyl)biphenyl-2-yl]-4,5-dihydrooxazole
  参考文献：
  名称：

  钌（IV）亚烷基作为烯烃与芳基氯直接芳基化的预催化剂，并应用于顺序催化。

  摘要：

  DOI：

  10.1002/anie.200701727
• 作为产物：
  描述：

  对氯苯乙酮 、 2-(o-tolyl)-4,5-dihydrooxazole 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2,4,6-三甲基苯甲酸 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以92%的产率得到1-[2'-(4,5-dihydro-1,3-oxazol-2-yl)-3'-methyl-biphenyl-4-yl]-ethanone
  参考文献：
  名称：

  辅助钌催化的CH键活化：羧酸作为助催化剂，通常用于非极性溶剂中的直接芳基化。

  摘要：

  催化量的芳族羧酸MesCO H通过一致的去质子化-金属化机理在无极性溶剂中实现了钌催化的直接芳基化，具有无与伦比的广泛范围。

  DOI：

  10.1021/ol800773x

文献信息

• Single-Component Phosphinous Acid Ruthenium(II) Catalysts for Versatile C−H Activation by Metal-Ligand Cooperation
  作者：Daniel Zell、Svenja Warratz、Dmitri Gelman、Simon J. Garden、Lutz Ackermann

  DOI：10.1002/chem.201504851

  日期：2016.1.22

  Well‐defined ruthenium(II) phosphinous acid (PA) complexes enabled chemo‐, site‐, and diastereoselective C−H functionalization of arenes and alkenes with ample scope. The outstanding catalytic activity was reflected by catalyst loadings as low as 0.75 mol %, and the most step‐economical access reported to date to angiotensin II receptor antagonist blockbuster drugs. Mechanistic studies indicated a

  明确定义的次膦酸亚膦酸钌（II）配合物可在广泛的范围内实现芳烃和烯烃的化学，位点和非对映选择性CH功能化。低至0.75 mol％的催化剂载量反映了其出色的催化活性，并且据报道是迄今为止获得血管紧张素II受体拮抗剂重磅炸弹药物最省钱的途径。机理研究表明，通过单电子转移（SET）型基本过程可发生动力学相关的C-X裂解，并为PA辅助的C-H钌化步骤提供了证据。
• Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C–H/C–O Bond Arylations with Phenols in Water
  作者：Lutz Ackermann、Jola Pospech、Harish Kumar Potukuchi

  DOI：10.1021/ol300671y

  日期：2012.4.20

  [Ru(O2CMes)2(p-cymene)] enabled efficient direct arylations of unactivated C–H bonds with easily available, inexpensive phenols. Extraordinary chemoselectivity of the well-defined ruthenium catalyst set the stage for challenging C–H/C–O bond functionalizations to occur under solvent-free conditions as well as in water, and allowed first direct C–H bond arylations with user-friendly diaryl sulfates as electrophiles

  钌（II）羧酸盐络合物[Ru（O 2 CMes）2（p- Cymene）]使未活化的C–H键与容易获得的廉价酚有效地直接芳基化。明确定义的钌催化剂的非凡的化学选择性为挑战性的C–H / C–O键功能化在无溶剂条件下以及在水中的条件奠定了基础，并允许使用用户友好的二芳基首次进行直接的C–H键芳基化硫酸盐为亲电试剂。
• [RuCl₃(H₂O)_n]-Catalyzed Direct Arylations with Bromides as Electrophiles
  作者：Lutz Ackermann、Andreas Althammer、Robert Born

  DOI：10.1055/s-2007-990838

  日期：——

  Catalytic amounts of [RuCl3(H2O)n] allow for direct ­arylations via C-H bond functionalization with aryl bromides, ­bearing a variety of important functional groups.

  催化量的[RuCl3(H2O)n]可以通过 C-H 键官能化直接与芳基溴化物发生芳基化反应，芳基溴化物含有多种重要的官能团。
• Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C−H and C−OH Bond Functionalizations
  作者：Lutz Ackermann、Michael Mulzer

  DOI：10.1021/ol802252m

  日期：2008.11.6

  Phenols can be employed as proelectrophiles in operationally simple ruthenium-catalyzed dehydrative direct arylations, proceeding through chemo- and regioselective functionalizations of C-H and C-OH bonds.
• [RuCl3(H2O)n]-catalyzed direct arylations
  作者：Lutz Ackermann、Andreas Althammer、Robert Born

  DOI：10.1016/j.tet.2008.01.050

  日期：2008.6

  Catalytic amounts of economically attractive [RuCl3(H2O)(n)] allow for direct arylations via C-H bond functionalization with aryl bromides under phosphine ligand-free reaction conditions. Thereby, a variety of functionalized (hetero)aryl bromides, bearing either electron-withdrawing or electron-releasing substituents, can be employed for direct arylations of pyridine, oxazoline, pyrazole, or ketimine derivatives as pronucleophiles. (C) 2008 Elsevier Ltd. All rights reserved.