2,2-di-tert-butyl-3-methyl-4-phenyl-5-propyloxasilacyclopentene | 749862-88-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,2-di-tert-butyl-3-methyl-4-phenyl-5-propyloxasilacyclopentene
• 英文别名: 2,2-ditert-butyl-3-methyl-4-phenyl-5-propyl-5H-oxasilole
• CAS: 749862-88-2
• 化学式: C₂₁H₃₄OSi
• 分子量: 330.586
• InChiKey: WLDYNGSEVYTROK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-di-tert-butyl-3-methyl-4-phenyl-5-propyloxasilacyclopentene 在 camphor-10-sulfonic acid 、 四丁基氟化铵 N-甲基吡咯烷酮 、 叔丁基过氧化氢 、 palladium dihydroxide 、 氢气 、 potassium hydride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 、 苯 为溶剂， 反应 149.0h， 生成 (2SR,4SR,5RS,6SR)-4-methyl-2-(p-nitrophenyl)-5-phenyl-6-propyl-1,3-dioxane
  参考文献：
  名称：

  Formation and Utility of Oxasilacyclopentenes Derived from Functionalized Alkynes

  摘要：

  Oxasilacyclopentenes were shown to be synthetically useful masked allylic alcohols constructed in high yields and regioselectivities from terminal and internal alkynes. Several functional groups were shown to be tolerated utilizing silver-catalyzed silacyclopropenation of alkynes. In situ insertion of various carbonyl compounds into silacyclopropenes afforded regioselective formation of oxasilacyclopentenes. Elaboration of the oxasilacyclopentenes displayed the synthetic utility of these substrates. Both diastereoselective hydrogenation and Diels-Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.

  DOI：

  10.1021/ja047498f
• 作为产物：
  描述：

  1-苯基-1-丙炔 、 正丁醛 、 7,7-di-tert-butyl-7-silabicyclo[4.1.0]heptane 在 silver orthophosphate 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 14.5h， 以54%的产率得到2,2-di-tert-butyl-3-methyl-4-phenyl-5-propyloxasilacyclopentene
  参考文献：
  名称：

  Formation and Utility of Oxasilacyclopentenes Derived from Functionalized Alkynes

  摘要：

  Oxasilacyclopentenes were shown to be synthetically useful masked allylic alcohols constructed in high yields and regioselectivities from terminal and internal alkynes. Several functional groups were shown to be tolerated utilizing silver-catalyzed silacyclopropenation of alkynes. In situ insertion of various carbonyl compounds into silacyclopropenes afforded regioselective formation of oxasilacyclopentenes. Elaboration of the oxasilacyclopentenes displayed the synthetic utility of these substrates. Both diastereoselective hydrogenation and Diels-Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.

  DOI：

  10.1021/ja047498f