4-(furan-2-yl)-2-isopropyl-5-methylphenol | 1251914-04-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(furan-2-yl)-2-isopropyl-5-methylphenol
• 英文别名: 4-(Furan-2-yl)-5-methyl-2-propan-2-ylphenol
• CAS: 1251914-04-1
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: KDAKFEXJQITLSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-呋喃硼酸 、 4-氯-2-异丙基-5-甲基苯酚 在 C₄₆H₆₄ClPPd 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到4-(furan-2-yl)-2-isopropyl-5-methylphenol
  参考文献：
  名称：

  Design of a Versatile and Improved Precatalyst Scaffold for Palladium-Catalyzed Cross-Coupling: (η³-1-^tBu-indenyl)₂(μ-Cl)₂Pd₂

  摘要：

  We describe the development of (eta(3)-1-Bu-t-indenyl)(2)(mu-Cl)(2)Pd-2, a versatile precatalyst scaffold for Pd-catalyzed cross-coupling. Our new system is more active than commercially available (eta(3)-cinnamyl)(2)(mu-Cl)(2)Pd-2 and is compatible with a range of NHC and phosphine ligands. Precatalysts of the type (eta(3)-1-Bu-t-indenyl)Pd(Cl)(L) can either be isolated through the reaction of (eta(3)-1-Bu-t-indenyl)(2)(mu-Cl)(2)Pd-2 with the appropriate ligand or generated in situ, which offers advantages for ligand screening. We show that the (eta(3)-1-Bu-t-indenyl)(2)(mu-Cl)(2)Pd-2 scaffold generates highly active systems for a number of challenging cross-coupling reactions. The reason for the improved catalytic activity of systems generated from the (eta(3)-1-Bu-t-indenyl)(2)(mu-Cl)(2)Pd-2 scaffold compared to (eta(3)-cinnamyl)(2)(mu-Cl)(2)Pd-2 is that inactive Pd-I dimers are not formed during catalysis.

  DOI：

  10.1021/acscatal.5b00878

文献信息

• [EN] NOVEL PRECATALYST SCAFFOLDS FOR CROSS-COUPLING REACTIONS, AND METHODS OF MAKING AND USING SAME<br/>[FR] NOUVEAUX SUPPORTS DE PRÉ-CATALYSEURS POUR RÉACTIONS À COUPLAGE MUTUEL, ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV YALE

  公开号：WO2016057600A1

  公开（公告）日：2016-04-14

  The present invention provides novel transition-metal precatalysts that are useful in preparing active coupling catalysts. In certain embodiments, the precatalysts of the invention are air-stable and moisture-stable. The present invention further provides methods of making and using the precatalysts of the invention.

  本发明提供了新型过渡金属前催化剂，可用于制备活性偶联催化剂。在某些实施例中，本发明的前催化剂具有空气稳定性和湿度稳定性。本发明还提供了制备和使用本发明的前催化剂的方法。
• Precatalyst scaffolds for cross-coupling reactions, and methods of making and using same
  申请人：YALE UNIVERSITY

  公开号：US10894802B2

  公开（公告）日：2021-01-19

  The present invention provides novel transition-metal precatalysts that are useful in preparing active coupling catalysts. In certain embodiments, the precatalysts of the invention are air-stable and moisture-stable. The present invention further provides methods of making and using the precatalysts of the invention.

  本发明提供了可用于制备活性偶联催化剂的新型过渡金属前催化剂。在某些实施方案中，本发明的前催化剂具有空气稳定性和湿度稳定性。本发明进一步提供了制造和使用本发明前催化剂的方法。
• A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids
  作者：Tom Kinzel、Yong Zhang、Stephen L. Buchwald

  DOI：10.1021/ja1073799

  日期：2010.10.13

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.
• NOVEL PRECATALYST SCAFFOLDS FOR CROSS-COUPLING REACTIONS, AND METHODS OF MAKING AND USING SAME
  申请人：Yale University

  公开号：EP3204395B1

  公开（公告）日：2020-05-27