diethyl 3-methyl-2-trimethylsilyl-indene-1,1-dicarboxylate | 869472-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: diethyl 3-methyl-2-trimethylsilyl-indene-1,1-dicarboxylate
• 英文别名: Diethyl 3-methyl-2-trimethylsilylindene-1,1-dicarboxylate；diethyl 3-methyl-2-trimethylsilylindene-1,1-dicarboxylate
• CAS: 869472-18-4
• 化学式: C₁₉H₂₆O₄Si
• 分子量: 346.499
• InChiKey: DNRXGEJNPBQSSX-UHFFFAOYSA-N

物化性质

• 沸点：
  378.9±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘苯乙酸 在 硫酸 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 63.0h， 生成 diethyl 3-methyl-2-trimethylsilyl-indene-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of Indenes by the Palladium-Catalyzed Carboannulation of Internal Alkynes

  摘要：

  [GRAPHICS]A number of highly substituted indenes have been prepared in good yields by treating functionally substituted aryl halides with various internal alkynes in the presence of a palladium catalyst. The reaction is believed to proceed by regioselective arylpalladation of the alkyne and subsequent nucleophilic displacement of the palladium in the resulting vinylpalladium intermediate.

  DOI：

  10.1021/ol051907a

文献信息

• Synthesis of Indenes by the Transition Metal-Mediated Carboannulation of Alkynes
  作者：Daohua Zhang、Zhijian Liu、Eul K. Yum、Richard C. Larock

  DOI：10.1021/jo0620563

  日期：2007.1.1

  The synthesis of highly substituted indenes has been achieved by three different transition metal-mediated methods. The first method involves the palladium-catalyzed carboannulation of internal alkynes. The second method utilizes a two-step approach, which involves first the palladium/copper-catalyzed cross-coupling of terminal alkynes with appropriately functionalized aryl halides, followed by copper-catalyzed

  通过三种不同的过渡金属介导的方法可以实现高度取代的茚的合成。第一种方法涉及内部炔烃的钯催化碳环化反应。第二种方法采用两步法，其中首先涉及末端炔烃与适当官能化的芳基卤化物的钯/铜催化交叉偶联，然后进行铜催化的分子内环化。第三种方法涉及在第二种方法的第一步中形成的芳基炔烃的分子间钯催化的芳基化。
• Synthesis of Indenes by the Palladium-Catalyzed Carboannulation of Internal Alkynes
  作者：Daohua Zhang、Eul Kgun Yum、Zhijian Liu、Richard C. Larock

  DOI：10.1021/ol051907a

  日期：2005.10.1

  [GRAPHICS]A number of highly substituted indenes have been prepared in good yields by treating functionally substituted aryl halides with various internal alkynes in the presence of a palladium catalyst. The reaction is believed to proceed by regioselective arylpalladation of the alkyne and subsequent nucleophilic displacement of the palladium in the resulting vinylpalladium intermediate.