1-(6-(2-hydroxy-[1,1'-biphenyl]-3-yl)pyridin-2-yl)ethan-1-one | 866613-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(6-(2-hydroxy-[1,1'-biphenyl]-3-yl)pyridin-2-yl)ethan-1-one
• 英文别名: 2-[(2-hydroxy-3-phenyl)phenyl]-6-acetylpyridine
• CAS: 866613-60-7
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: SUYQFCHICRNNDP-UHFFFAOYSA-N

物化性质

• 沸点：
  456.9±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(6-(2-hydroxy-[1,1'-biphenyl]-3-yl)pyridin-2-yl)ethan-1-one 、 2,6-二异丙基苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以61%的产率得到(E)-3-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)-[1,1'-biphenyl]-2-ol
  参考文献：
  名称：

  Use of Suzuki cross-coupling as a route to 2-phenoxy-6-iminopyridines and chiral 2-phenoxy-6-(methanamino)pyridines

  摘要：

  The anisyl boronic acids, 2-OMe-3-R-2-5-R-1-C6H2B(OH)(2) (R-1=R-2=H (a); R-1=H, R-2=Ph (b); R-1=Me, R-2=H (c); R-1=Cl, R-2=H (d); R-1=t-Bu, R-2=H (e)), have been employed in Suzuki cross-coupling reactions with either 2-bromo-6-formylpyridine (1) or 2-bromo-6-acetylpyridine (11) generating, following a facile deprotection step, the 2-phenoxy-6-carbonylpyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CH=O)C5H3N (R-1=R-2=H (1a); R-1=Me, R-2=H (1c); R-1=Cl, R-2=H (1d); R-1=t-Bu, R-2=H (1e)) and 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CMe=O)C5H3N (R-1=R-2=H (2a); R-1=H, R-2=Ph (2b)). Condensation reactions of 1 and 2 with 2,6-diisopropylaniline proceed smoothly to give the 2-phenoxy-6-iminopyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CH=N(2,6-i-Pr2C6H3)}C5H3N (R-1=R-2=H (3a); R-1=Me, R-2=H (3c); R-1=Cl, R-2=H (3d); R-1=t-Bu, R-2=H (3e)) and 2-(2'-OH-3'-R-2-5'-R-2-C6H2)-6-{CMe=N(2,6-i-Pr2C6H3)}C5H3N (R-1=H, R-2=Ph (4a), R-1=H, R-2=Ph (4b)). Reduction of the imino unit (and concomitant C-C bond formation) in 3 can be achieved by treatment with trimethylaluminium or methyllithium which, following hydrolysis, furnishes the racemic chiral 2-phenoxy-6-(methanamino)pyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CHMe-NH(2,6-i-Pr2C6H3)}C5H3N {R-1=R-2=H (5a); R-1=Me, R-2=H (5c); R-1=Cl, R-2=H (5d); R-1=t-Bu, R-2=H (5e)). This work represents a straightforward and rapid synthetic route to libraries of sterically and electronically variable phenoxy-substituted imino- and methanamino-pyridines, which are expected to act as useful ligands or proligands for late and early transition metal-mediated alkene polymerisation catalysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.019
• 作为产物：
  描述：

  1-[6-(2-methoxy-3-phenylphenyl)pyridin-2-yl]ethanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以0.44 g的产率得到1-(6-(2-hydroxy-[1,1'-biphenyl]-3-yl)pyridin-2-yl)ethan-1-one
  参考文献：
  名称：

  Use of Suzuki cross-coupling as a route to 2-phenoxy-6-iminopyridines and chiral 2-phenoxy-6-(methanamino)pyridines

  摘要：

  The anisyl boronic acids, 2-OMe-3-R-2-5-R-1-C6H2B(OH)(2) (R-1=R-2=H (a); R-1=H, R-2=Ph (b); R-1=Me, R-2=H (c); R-1=Cl, R-2=H (d); R-1=t-Bu, R-2=H (e)), have been employed in Suzuki cross-coupling reactions with either 2-bromo-6-formylpyridine (1) or 2-bromo-6-acetylpyridine (11) generating, following a facile deprotection step, the 2-phenoxy-6-carbonylpyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CH=O)C5H3N (R-1=R-2=H (1a); R-1=Me, R-2=H (1c); R-1=Cl, R-2=H (1d); R-1=t-Bu, R-2=H (1e)) and 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CMe=O)C5H3N (R-1=R-2=H (2a); R-1=H, R-2=Ph (2b)). Condensation reactions of 1 and 2 with 2,6-diisopropylaniline proceed smoothly to give the 2-phenoxy-6-iminopyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CH=N(2,6-i-Pr2C6H3)}C5H3N (R-1=R-2=H (3a); R-1=Me, R-2=H (3c); R-1=Cl, R-2=H (3d); R-1=t-Bu, R-2=H (3e)) and 2-(2'-OH-3'-R-2-5'-R-2-C6H2)-6-{CMe=N(2,6-i-Pr2C6H3)}C5H3N (R-1=H, R-2=Ph (4a), R-1=H, R-2=Ph (4b)). Reduction of the imino unit (and concomitant C-C bond formation) in 3 can be achieved by treatment with trimethylaluminium or methyllithium which, following hydrolysis, furnishes the racemic chiral 2-phenoxy-6-(methanamino)pyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-{CHMe-NH(2,6-i-Pr2C6H3)}C5H3N {R-1=R-2=H (5a); R-1=Me, R-2=H (5c); R-1=Cl, R-2=H (5d); R-1=t-Bu, R-2=H (5e)). This work represents a straightforward and rapid synthetic route to libraries of sterically and electronically variable phenoxy-substituted imino- and methanamino-pyridines, which are expected to act as useful ligands or proligands for late and early transition metal-mediated alkene polymerisation catalysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.019

文献信息

• 一种含氮芳氧基茂钛化合物及其制备方法和应用
  申请人：上海化工研究院有限公司

  公开号：CN111747995B

  公开（公告）日：2023-02-21

  本发明涉及一种含氮芳氧基茂钛化合物及其制备方法和应用，制备方法为：含氮酚类配体化合物与三氯化茂钛化合物在有机溶剂中反应，后经过滤、浓缩、重结晶，即得到含氮芳氧基茂钛化合物，该含氮芳氧基茂钛化合物是一种高效的烯烃聚合催化剂，可用于乙烯或α‑烯烃均聚、乙烯与α‑烯烃共聚、烯烃与极性单体共聚等聚合反应。与现有技术相比，本发明的含氮芳氧基茂钛化合物的优点十分明显：原料易得，合成路线简单，产品收率高，性质比较稳定，同时具有较高的催化活性，能获得超高分子量的聚乙烯、聚丙烯、高共聚单体含量的乙烯与α‑烯烃共聚物、烯烃与极性单体共聚物，能够满足工业应用的要求。