2,6-dimethyl-3'-methoxybiphenyl | 1132642-90-0

• 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: 2,6-dimethyl-3'-methoxybiphenyl
• 英文别名: 3'-methoxy-2,6-dimethylbiphenyl；2,6-dimethyl-3'-methoxydiphenyl；2-(3-Methoxyphenyl)-1,3-dimethylbenzene
• CAS: 1132642-90-0
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: IVQXJWGUHKWUCL-UHFFFAOYSA-N

物化性质

• 沸点：
  293.8±9.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 3-甲氧基苯硼酸 在 potassium phosphate 、 dicyclohexyl(2,4,6-trimethoxyphenyl)phosphonium tetrafluoroborate 、 水 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.5h， 以97%的产率得到2,6-dimethyl-3'-methoxybiphenyl
  参考文献：
  名称：

  易得且空气稳定的单膦酸酯HBF 4盐在芳基或1-烯基氯化物的Suzuki偶联反应中的应用

  摘要：

  在这封信中，将易于获得的单膦酸酯HBF 4盐用于有机硼酸的Suzuki偶联反应，以高产率至优异产率提供交叉偶联产物。芳基或1-烯基硼酸和氯化物均可使用。它也适用于空间受限的情况。

  DOI：

  10.1016/j.tetlet.2009.12.143

文献信息

• STRUCTURE AND METHOD FOR SYNTHESIZING AND USING DIALKYL(2,4,6- OR 2,6-ALKOXYPHENYL)PHOSPHINE AND ITS TETRAFLUOROBORATE
  申请人：Ma Shengming

  公开号：US20120197030A1

  公开（公告）日：2012-08-02

  The current invention relates to the structure, synthesis of dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine or its tetrafluoroborate, as well as its applications in the palladium catalyzed carbon-chlorine bond activation for Suzuki coupling reactions and carbon-nitrogen bond formation reactions. The dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine or its tetrafluoroborate could coordinate with the palladium catalyst to activate the inert carbon-chlorine bond highly selectively and catalyze Suzuki coupling reaction with arylboronic acid or carbon-nitrogen bond formation reaction with organic amines. The current invention uses only one step to synthesize dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine and its tetrafluoroborate is stable in the air. Compared with known synthetic routes of ligands used in activating carbon-chlorine bonds, the method of current invention is short, easy to operate. Moreover, with this type of ligands, the Suzuki coupling products of optically active chlorolactones and arylboronic acids would maintain their configuration and optical purity.

  当前的发明涉及二烷基(2,4,6-或2,6-烷氧基苯基)膦或其四氟硼酸盐的结构、合成，以及其在钯催化的碳-氯键活化苏齐反应和碳-氮键形成反应中的应用。二烷基(2,4,6-或2,6-烷氧基苯基)膦或其四氟硼酸盐可以与钯催化剂配位，高度选择性地活化惰性碳-氯键，并催化与芳基硼酸或有机胺进行苏齐偶联反应或碳-氮键形成反应。当前的发明仅使用一步合成二烷基(2,4,6-或2,6-烷氧基苯基)膦，其四氟硼酸盐在空气中稳定。与已知用于活化碳-氯键的配体的合成路线相比，当前发明的方法简短、易操作。此外，使用这种类型的配体，光学活性氯代内酯和芳基硼酸的苏齐偶联产物将保持其构型和光学纯度。
• Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation
  作者：M. Alexander Düfert、Kelvin L. Billingsley、Stephen L. Buchwald

  DOI：10.1021/ja4064469

  日期：2013.8.28

  mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.

  报道了使用预催化剂 P1 或 P2 的未受保护的富氮杂环的 Suzuki-Miyaura 交叉偶联。该程序允许各种取代的吲唑、苯并咪唑、吡唑、吲哚、羟吲哚和氮杂吲哚卤化物在温和条件下以良好至极好的产率反应。此外，基于通过实验、晶体学和理论研究获得的证据，描述了未受保护的唑类对 Pd 催化的交叉偶联反应的抑制作用背后的机制。
• Efficient Synthesis of Biaryls through the Kumada Reaction Catalyzed by Carbene Adducts of Cyclopalladated Ferrocenylimine
  作者：Gerui Ren、Xiuling Cui、Yangjie Wu

  DOI：10.1002/ejoc.200901495

  日期：2010.4

  A series of carbene adducts of cyclopalladated ferrocenylimine were prepared and evaluated in the cross-coupling reaction of aryl halides with Grignard reagents (the Kumada reaction). Complex d exhibited high catalytic activity for the coupling of aryl chlorides with sterically hindered Grignard reagents and the reaction tolerated various functional groups. A wide range of biaryls were efficiently

  在芳基卤化物与格氏试剂（Kumada 反应）的交叉偶联反应中制备并评估了一系列环钯化二茂铁亚胺的卡宾加合物。配合物 d 对芳基氯与位阻格氏试剂的偶联表现出高催化活性，并且该反应可以耐受各种官能团。在温和的反应条件下，在 0.5 mol% 催化剂的存在下，以良好到极好的收率有效地获得了广泛的联芳基化合物。
• 2,4,6- OR 2,6-ALKOXYPHENYL DIALKYLPHOSPHINE, TETRAFLUOROBORATE, PREPARATION METHOD AND USE THEREOF
  申请人：Zhejiang University

  公开号：EP2492274A1

  公开（公告）日：2012-08-29

  The current invention relates to the structure, synthesis of dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine or its tetrafluoroborate, as well as its applications in the palladium catalyzed carbon-chlorine bond activation for Suzuki coupling reactions and carbon-nitrogen bond formation reactions. The dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine or its tetrafluoroborate could coordinate with the palladium catalyst to activate the inert carbon-chlorine bond highly selectively and catalyze Suzuki coupling reaction with arylboronic acid or carbon-nitrogen bond formation reaction with organic amines. The current invention uses only one step to synthesize dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine and its tetrafluoroborate is stable in the air. Compared with known synthetic routes of ligands used in activating carbon-chlorine bonds, the method of current invention is short, easy to operate. Moreover, with this type of ligands, the Suzuki coupling products of optically active chlorolactones and arylboronic acids would maintain their configuration and optical purity.

  本发明涉及二烷基（2,4,6-或 2,6-烷氧基苯基）膦或其四氟硼酸盐的结构、合成及其在钯催化的碳-氯键活化中的应用，用于铃木偶联反应和碳-氮键形成反应。二烷基（2,4,6- 或 2,6- 烷氧基苯基）膦或其四氟硼酸盐可与钯催化剂配位，高选择性地活化惰性碳-氯键，催化与芳基硼酸的铃木偶联反应或与有机胺的碳-氮键形成反应。本发明只需一步即可合成二烷基（2,4,6-或 2,6-烷氧基苯基）膦，其四氟硼酸盐在空气中稳定。与已知的用于活化碳-氯键的配体合成路线相比，本发明的方法时间短，易于操作。此外，使用这类配体，光学活性氯内酯和芳基硼酸的铃木偶联产物将保持其构型和光学纯度。
• 2,4,6- OR 2,6-ALKOXYPHENYL DIALKYLPHOSPHINE, TETRAFLUOROBORATE AND USE THEREOF
  申请人：Zhejiang University

  公开号：EP2492274B1

  公开（公告）日：2016-09-21