2-(4'-methoxyphenyl)-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(4'-methoxyphenyl)-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indole
• 英文别名: 2-(4-methoxyphenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indole；2-[[2-(4-Methoxyphenyl)indol-1-yl]methoxy]ethyl-trimethylsilane
• 化学式: C₂₁H₂₇NO₂Si
• 分子量: 353.536
• InChiKey: KERSSJHJLFLKQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(hydroxydimethylsilyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indole sodium salt 、 4-氯苯甲醚 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94%的产率得到2-(4'-methoxyphenyl)-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-indole
  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

• 2-(Tributylstannyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indole: Synthesis and use as a 1H-indol-2-yl-anion equivalent
  作者：Giovanni Palmisano、Marco Santagostino

  DOI：10.1002/hlca.19930760622

  日期：1993.9.22

  Pd-Catalyzed reaction of 2-(tributylstannyl)-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-indole (5) with a variety of aryl, heteroaryl, vinyl, and allyl halides provides an efficient entry to the corresponding cross-coupled products (see Table).

  2-（三丁基锡烷基）-1-[[2-（三甲基甲硅烷基）乙氧基]甲基} -1 H-吲哚（5）与各种芳基，杂芳基，乙烯基和烯丙基卤化物的钯催化反应提供了有效的途径相应的交叉耦合产品（请参见表）。