(+/-)-tert-butyl[(5-oxiran-2-ylpent-4-ynyl)oxy]diphenylsilane | 931429-25-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+/-)-tert-butyl[(5-oxiran-2-ylpent-4-ynyl)oxy]diphenylsilane
• 英文别名: Tert-butyl-[5-(oxiran-2-yl)pent-4-ynoxy]-diphenylsilane
• CAS: 931429-25-3
• 化学式: C₂₃H₂₈O₂Si
• 分子量: 364.56
• InChiKey: XDTCEYABOKVVQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-tert-butyl[(5-oxiran-2-ylpent-4-ynyl)oxy]diphenylsilane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 三氟化硼乙醚 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.17h， 生成 (+/-)-3-{1-[tert-butyl(diphenyl)silyl]vinyl}cyclopent-3-en-1-ol
  参考文献：
  名称：

  Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes

  摘要：

  beta,gamma-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)(3) or BF3 center dot OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.

  DOI：

  10.1021/jo062107w
• 作为产物：
  描述：

  tert-butyl-pent-4-ynyloxy-diphenyl-silane 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 (+/-)-tert-butyl[(5-oxiran-2-ylpent-4-ynyl)oxy]diphenylsilane
  参考文献：
  名称：

  Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes

  摘要：

  beta,gamma-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)(3) or BF3 center dot OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.

  DOI：

  10.1021/jo062107w

文献信息

• Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes
  作者：Letian Wang、Matthew L. Maddess、Mark Lautens

  DOI：10.1021/jo062107w

  日期：2007.3.1

  beta,gamma-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)(3) or BF3 center dot OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.