1,1-dimethyl-2,4-bis(4-dimethylaminophenyl)silole | 1006881-74-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,1-dimethyl-2,4-bis(4-dimethylaminophenyl)silole
• 英文别名: 4-[4-[4-(dimethylamino)phenyl]-1,1-dimethylsilol-2-yl]-N,N-dimethylaniline
• CAS: 1006881-74-8
• 化学式: C₂₂H₂₈N₂Si
• 分子量: 348.563
• InChiKey: PTIZPCQDFSUNFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(diethylamino)dimethylsilyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 4-二甲基氨基苯乙炔 在 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以80%的产率得到1,1-dimethyl-2,4-bis(4-dimethylaminophenyl)silole
  参考文献：
  名称：

  Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles

  摘要：

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.

  DOI：

  10.1021/ja073896h

文献信息

• Silylboranes Bearing Dialkylamino Groups on Silicon as Silylene Equivalents:  Palladium-Catalyzed Regioselective Synthesis of 2,4-Disubstituted Siloles
  作者：Toshimichi Ohmura、Kohei Masuda、Michinori Suginome

  DOI：10.1021/ja073896h

  日期：2008.2.6

  Silylpinacolboranes bearing dialkylamino groups on the silicon atom several as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2, 4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kasugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel Pi-conjugated siloles with good total yields.