(2-methoxyphenyl)triethylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-methoxyphenyl)triethylsilane
• 英文别名: triethyl(2-methoxyphenyl)silane；triethyl-(2-methoxyphenyl)silane
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: GPUHWAMFXFSWTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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-甲氧基苯基苯醚 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 85.0h， 生成 (2-methoxyphenyl)triethylsilane
  参考文献：
  名称：

  [EN] SILYLATION OF AROMATIC HETEROCYCLES BY EARTH ABUNDANT TRANSITION-METAL-FREE CATALYSTS
  [FR] SILYLATION D'HÉTÉROCYCLES AROMATIQUES PAR DES CATALYSEURS ABONDANTS SUR TERRE, EXEMPTS DE MÉTAUX DE TRANSITION

  摘要：

  公开号：

  WO2016022624A9

文献信息

• Silylation of C–H bonds in aromatic heterocycles by an Earth-abundant metal catalyst
  作者：Anton A. Toutov、Wen-Bo Liu、Kerry N. Betz、Alexey Fedorov、Brian M. Stoltz、Robert H. Grubbs

  DOI：10.1038/nature14126

  日期：2015.2.5

  and complex molecule synthesis, because these compounds have very useful physicochemical properties. Many of the methods now used to construct heteroaromatic C–Si bonds involve stoichiometric reactions between heteroaryl organometallic species and silicon electrophiles or direct, transition-metal-catalysed intermolecular carbon–hydrogen (C–H) silylation using rhodium or iridium complexes in the presence

  含有碳-硅 (C-Si) 键的杂芳族化合物在有机电子学和光子学、药物发现、核医学和复杂分子合成等领域具有重要意义，因为这些化合物具有非常有用的物理化学性质。现在用于构建杂芳族 C-Si 键的许多方法涉及杂芳基有机金属物质与硅亲电试剂之间的化学计量反应，或在存在以下情况时使用铑或铱配合物直接、过渡金属催化的分子间碳氢 (C-H) 硅烷化过量的氢受体。这两种方法都是有用的，但它们的局限性包括官能团不兼容、应用范围窄、催化剂的成本高和可用性低，以及未经证实的可扩展性。为此原因，非常需要一种新的通用催化方法来构建杂芳族 C-Si 键，以避免此类限制。在这里，我们报告了一个由地球丰富的碱金属物种催化的交叉脱氢杂芳族 C-H 官能化的例子。我们发现，容易获得且廉价的叔丁醇钾可催化芳香杂环与氢硅烷的直接硅烷化，一步提供杂芳基硅烷。甲硅烷基化在温和条件下进行，不存在氢受体、配体或添加剂，并且在任选的无溶剂条件下可放大到大于
• Base-Mediated Defluorosilylation of C(sp² )−F and C(sp³ )−F Bonds
  作者：Xiang-Wei Liu、Cayetana Zarate、Ruben Martin

  DOI：10.1002/anie.201813294

  日期：2019.2.11

  The ability to selectively forge C–heteroatom bonds by C−F scission is typically accomplished by metal catalysts, specialized ligands and/or harsh reaction conditions. Described herein is a base‐mediated defluorosilylation of unactivated C(sp2)−F and C(sp3)−F bonds that obviates the need for metal catalysts. This protocol is characterized by its simplicity, mild reaction conditions, and wide scope

  通常通过金属催化剂，特殊的配体和/或苛刻的反应条件来实现通过C-F断裂选择性地伪造C-杂原子键的能力。本文描述的是未激活的C（sp 2）-F和C（sp 3）-F键的碱介导的脱氟甲硅烷基化，无需金属催化剂。该协议的特点是简单，反应条件温和且范围广泛，即使在后期功能化的背景下，也构成了现有C-Si键形成协议的一种补充方法。
• TRANSITION-METAL-FREE SILYLATION OF AROMATIC COMPOUNDS
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140094607A1

  公开（公告）日：2014-04-03

  The present invention describes chemical systems and methods for silylating aromatic organic substrates, said system comprising a mixture of (a) at least one organosilane and (b) at least one strong base, said system being substantially free of a transition-metal compound, and said methods comprising contacting a quantity of the organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate; wherein said system is substantially free of a transition-metal compound.

  本发明描述了用于硅烷化芳香有机底物的化学体系和方法，该体系包括至少一种有机硅烷和至少一种强碱的混合物，该体系基本上不含过渡金属化合物，该方法包括将一定量的有机底物与至少一种有机硅烷和至少一种强碱的混合物接触，在足够的条件下硅烷化芳香底物；其中该体系基本上不含过渡金属化合物。
• Transition-metal-free silylation of aromatic compounds
  申请人：California Institute of Technology

  公开号：US09000167B2

  公开（公告）日：2015-04-07

  The present invention describes chemical systems and methods for silylating aromatic organic substrates, said system comprising a mixture of (a) at least one organosilane and (b) at least one strong base, said system being substantially free of a transition-metal compound, and said methods comprising contacting a quantity of the organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate; wherein said system is substantially free of a transition-metal compound.

  本发明描述了用于硅烷化芳香有机底物的化学系统和方法，该系统包括混合物(a)至少一种有机硅烷和(b)至少一种强碱，该系统基本上不含有过渡金属化合物，该方法包括将一定量的有机底物与混合物(a)至少一种有机硅烷和(b)至少一种强碱接触，在足够的条件下硅烷化芳香底物；其中该系统基本上不含有过渡金属化合物。
• SILYLATION OF AROMATIC HETEROCYCLES BY EARTH ABUNDANT TRANSITION-METAL-FREE CATALYSTS
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20160046653A1

  公开（公告）日：2016-02-18

  The present invention describes chemical systems and methods for silylating aromatic organic substrates, said system or method comprising or consisting essentially of a mixture of (a) at least one organosilane and (b) at least one strong base, the definition of strong base now also including hydroxide, especially KOH, said system being preferably, but not necessarily substantially free of a transition-metal compound, and said methods comprising contacting a quantity of the organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate; wherein said system is substantially free of a transition-metal compound.

  本发明描述了用于硅烷化芳香有机基质的化学系统和方法，该系统或方法包括或基本上由以下混合物组成：（a）至少一种有机硅烷和（b）至少一种强碱，强碱的定义现在还包括氢氧化物，特别是KOH，该系统最好是但不一定完全不含过渡金属化合物，该方法包括将有机基质的数量与（a）至少一种有机硅烷和（b）至少一种强碱的混合物接触，在足够的条件下硅烷化芳香基质；其中所述系统基本上不含过渡金属化合物。