triisopropyl(8-(tetrahydrofuran-2-yl)octa-1,6-diyn-1-yl)silane | 1427728-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: triisopropyl(8-(tetrahydrofuran-2-yl)octa-1,6-diyn-1-yl)silane
• 英文别名: 8-(Oxolan-2-yl)octa-1,6-diynyl-tri(propan-2-yl)silane；8-(oxolan-2-yl)octa-1,6-diynyl-tri(propan-2-yl)silane
• CAS: 1427728-93-5
• 化学式: C₂₁H₃₆OSi
• 分子量: 332.602
• InChiKey: LLEREQNDSGKOEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,6-庚二炔 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 、 双(2-二苯基磷苯基)醚 、 lithium hexamethyldisilazane 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 62.5h， 生成 triisopropyl(8-(tetrahydrofuran-2-yl)octa-1,6-diyn-1-yl)silane
  参考文献：
  名称：

  Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes

  摘要：

  Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this context oxy- and aminoalkynylation are especially important reactions because of the numerous transformations possible with the triple bond of acetylenes yet these methods have been limited to the use of silyl protected acetylenes. Herein we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.

  DOI：

  10.1021/jo400254q

文献信息

• Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes
  作者：Stefano Nicolai、Raha Sedigh-Zadeh、Jérôme Waser

  DOI：10.1021/jo400254q

  日期：2013.4.19

  Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this context oxy- and aminoalkynylation are especially important reactions because of the numerous transformations possible with the triple bond of acetylenes yet these methods have been limited to the use of silyl protected acetylenes. Herein we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.