1-(2,6-二甲基苯基)-3,5-二甲氧基苯 | 606970-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,6-二甲基苯基)-3,5-二甲氧基苯
• 英文名称: 2,6-dimethyl-3',5'-dimethoxybiphenyl
• 英文别名: 3',5'-dimethoxy-2,6-dimethylbiphenyl；2,6-dimethyl-3',5'-dimethoxydiphenyl；3',5'-Dimethoxy-2,6-dimethyl-1,1'-biphenyl；1-(2,6-dimethylphenyl)-3,5-dimethoxybenzene
• CAS: 606970-71-2
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: ILLXGIMWZQTOOD-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±37.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯-1,3-二甲苯 、 2-(3,5-二甲氧基)-苯基-4,4,5,5-四甲基-(1,3,2)-二噁硼烷 在 tris(dibenzylideneacetone)dipalladium (0) potassium phosphate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以115 mg的产率得到1-(2,6-二甲基苯基)-3,5-二甲氧基苯
  参考文献：
  名称：

  钯催化芳基氯化物的硼化：范围，应用和计算研究。

  摘要：

  DOI：

  10.1002/anie.200701551

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。
• Application of a readily available and air stable monophosphine HBF4 salt for the Suzuki coupling reaction of aryl or 1-alkenyl chlorides
  作者：Bo Lü、Chunling Fu、Shengming Ma

  DOI：10.1016/j.tetlet.2009.12.143

  日期：2010.3

  In this Letter, a readily available monophosphine HBF4 salt was applied for the Suzuki coupling reactions of organoboronic acids to afford the cross-coupling products in high to excellent yields. Both aryl or 1-alkenyl boronic acids and chlorides may be used. It is also suitable for sterically hindered cases.

  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。
• 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。
• An N-Heterocyclic Carbene Ligand with Flexible Steric Bulk Allows Suzuki Cross-Coupling of Sterically Hindered Aryl Chlorides at Room Temperature
  作者：Gereon Altenhoff、Richard Goddard、Christian W. Lehmann、Frank Glorius

  DOI：10.1002/anie.200351325

  日期：2003.8.11
• 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