4-bromo-2-(trimethylsilyl)benzonitrile | 1057732-31-6

• 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: 4-bromo-2-(trimethylsilyl)benzonitrile
• 英文别名: 4-Bromo-2-trimethylsilylbenzonitrile
• CAS: 1057732-31-6
• 化学式: C₁₀H₁₂BrNSi
• 分子量: 254.201
• InChiKey: AGNSMIGUDBSZIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(trimethylsilyl)benzonitrile 在 正丁基锂 、 硼酸三甲酯 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以84%的产率得到4-氰基-3-(三甲基甲硅烷基)苯基硼酸
  参考文献：
  名称：

  Selective Generation of Lithiated Benzonitriles: the Importance of Reaction Conditions

  摘要：

  Lithiated benzonitriles can be generated in high yields from reactions of bromobenzonitriles with n-BuLi in THF under standard cryogenic conditions (ca. -70 degrees C) provided the reverse addition mode is employed. The resultant aryllithiums are fairly stable at temperatures up to -60 degrees C. The formation of lithiated benzonitriles via Br/Li exchange under normal addition mode conditions is plagued by deprotonation and extensive CN-addition reactions. The generation of related aryllithiums from disilylated bromobenzonitriles is comparatively less sensitive to reaction conditions.

  DOI：

  10.1021/jo8013808
• 作为产物：
  描述：

  三甲基氯硅烷 、 4-溴苯腈 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以52%的产率得到4-bromo-2-(trimethylsilyl)benzonitrile
  参考文献：
  名称：

  Selective Generation of Lithiated Benzonitriles: the Importance of Reaction Conditions

  摘要：

  Lithiated benzonitriles can be generated in high yields from reactions of bromobenzonitriles with n-BuLi in THF under standard cryogenic conditions (ca. -70 degrees C) provided the reverse addition mode is employed. The resultant aryllithiums are fairly stable at temperatures up to -60 degrees C. The formation of lithiated benzonitriles via Br/Li exchange under normal addition mode conditions is plagued by deprotonation and extensive CN-addition reactions. The generation of related aryllithiums from disilylated bromobenzonitriles is comparatively less sensitive to reaction conditions.

  DOI：

  10.1021/jo8013808

文献信息

• Palladium-Catalyzed Intermolecular Coupling of 2-Silylaryl Bromides with Alkynes: Synthesis of Benzosiloles and Heteroarene-Fused Siloles by Catalytic Cleavage of the C(sp3)Si Bond
  作者：Yun Liang、Weizhi Geng、Junnian Wei、Zhenfeng Xi

  DOI：10.1002/anie.201108154

  日期：2012.2.20

  Unusual split: A wide variety of benzosiloles and derivatives are obtained by the Pd‐catalyzed intermolecular coupling of 2‐silylaryl bromides and alkynes and the accompanying selective cleavage of the C(sp3)Si bonds as a key step (see scheme). The product spectrum includes benzosiloles, benzothiophene‐fused siloles, ladder‐type π‐conjugated benzosiloles, and thiophene‐bridged 2,5‐bisbenzosiloles

  不寻常的分裂：通过Pd催化2-甲硅烷基芳基溴化物和炔烃的分子间偶联以及伴随的C（sp 3）Si键的选择性裂解作为关键步骤（参见方案），可以得到各种各样的苯并甲硅烷基及其衍生物。产品范围包括苯并甲硅烷，苯并噻吩稠合的甲硅烷，梯型π共轭苯并甲硅烷和噻吩桥联的2,5-双苯并甲硅烷。