3,7-dihydro-1,3,7-trimethyl-8-[1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indol-2-yl]-1H-purine-2,6-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3,7-dihydro-1,3,7-trimethyl-8-[1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indol-2-yl]-1H-purine-2,6-dione
• 英文别名: 1,3,7-Trimethyl-8-[1-(2-trimethylsilylethoxymethyl)indol-2-yl]purine-2,6-dione
• 化学式: C₂₂H₂₉N₅O₃Si
• 分子量: 439.589
• InChiKey: AHTCDWXKCKSWBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(hydroxydimethylsilyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indole sodium salt 、 8-氯-3,7-二氢-1,3,7-三甲基-1H-嘌呤-2,6-二酮 在 bis-(ϖ-allylpalladiumchloride) 2-双环己基膦-2',6'-二甲氧基联苯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以86%的产率得到3,7-dihydro-1,3,7-trimethyl-8-[1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indol-2-yl]-1H-purine-2,6-dione
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates

  摘要：

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.

  DOI：

  10.1021/jo7023784

文献信息

• Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
  作者：Scott E. Denmark、John D. Baird、Christopher S. Regens

  DOI：10.1021/jo7023784

  日期：2008.2.1

  The preparation of pi-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.