(2,4-diphenylnaphthalene-1-yl)trimethylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2,4-diphenylnaphthalene-1-yl)trimethylsilane
• 英文别名: (2,4-Diphenylnaphthalen-1-yl)-trimethylsilane
• 化学式: C₂₅H₂₄Si
• 分子量: 352.551
• InChiKey: HGAOBZLJLFDNFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-碘-2,2-二苯基乙烯 、 苯基乙炔基三甲基硅烷 在 palladium diacetate 、 sodium acetate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以19%的产率得到(2,4-diphenylnaphthalene-1-yl)trimethylsilane
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Internal Alkynes by Arene-Containing Vinylic Iodides and Triflates

  摘要：

  In the presence of a palladium catalyst, internal alkynes undergo carboannulation by cyclic and acyclic vinylic iodides and triflates bearing a neighboring aromatic ring to produce a variety of carbocycles. For example, a number of 9,10-disubstituted-1,2,3,4-tetrahydrophenanthrenes have been prepared in good yields through the palladium-catalyzed annulation of internal alkynes by 2-phenyl-1-cyclohexenyl triflate (1) or 1-iodo-2-phenylcyclohexene (2). This annulation process is fairly general and highly regioselective. The process appears to involve oxidative addition of the vinylic substrate to Pd(0) to produce a vinylic palladium intermediate, which adds the carbon moiety to the less hindered end and the palladium to the more hindered end of the alkyne, followed by intramolecular ring closure onto the neighboring aryl group. The scope and limitations of this methodology are discussed.

  DOI：

  10.1021/jo972154b

文献信息

• Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes
  作者：Dong Wei、Tian-Jiao Hu、Chen-Guo Feng、Guo-Qiang Lin

  DOI：10.1002/cjoc.201800169

  日期：2018.8

  The palladium catalyzed annulation of 1‐bromo‐2‐vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4‐palladium migration process is the key for success.

  为了有效合成取代的萘，实现了钯催化的1-溴-2-乙烯基苯衍生物与内部炔的环化反应。可控的芳基向乙烯基1,4-钯迁移过程是成功的关键。
• Palladium-Catalyzed Annulation of Internal Alkynes by Arene-Containing Vinylic Iodides and Triflates
  作者：Richard C. Larock、Qingping Tian

  DOI：10.1021/jo972154b

  日期：1998.3.1

  In the presence of a palladium catalyst, internal alkynes undergo carboannulation by cyclic and acyclic vinylic iodides and triflates bearing a neighboring aromatic ring to produce a variety of carbocycles. For example, a number of 9,10-disubstituted-1,2,3,4-tetrahydrophenanthrenes have been prepared in good yields through the palladium-catalyzed annulation of internal alkynes by 2-phenyl-1-cyclohexenyl triflate (1) or 1-iodo-2-phenylcyclohexene (2). This annulation process is fairly general and highly regioselective. The process appears to involve oxidative addition of the vinylic substrate to Pd(0) to produce a vinylic palladium intermediate, which adds the carbon moiety to the less hindered end and the palladium to the more hindered end of the alkyne, followed by intramolecular ring closure onto the neighboring aryl group. The scope and limitations of this methodology are discussed.