3-acetoxy-1-triethylsilyl-4-triisopropylsilylethynyl-6-triisopropylsilyl-hex-3-en-1,5-diyne | 500297-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetoxy-1-triethylsilyl-4-triisopropylsilylethynyl-6-triisopropylsilyl-hex-3-en-1,5-diyne
• 英文别名: [1-Triethylsilyl-6-tri(propan-2-yl)silyl-4-[2-tri(propan-2-yl)silylethynyl]hex-3-en-1,5-diyn-3-yl] acetate
• CAS: 500297-77-8
• 化学式: C₃₄H₆₀O₂Si₃
• 分子量: 585.106
• InChiKey: XMBADXWFKLQNJP-UHFFFAOYSA-N

物化性质

• 沸点：
  537.4±50.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 3-acetoxy-1-triethylsilyl-4-triisopropylsilylethynyl-6-triisopropylsilyl-hex-3-en-1,5-diyne 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.33h， 以81%的产率得到1-triethylsilyl-3-[[(trifluoromethyl)sulfonyl]oxy]-4-triisopropylsilylethynyl-6-triisopropylsilyl-hex-3-en-1,5-diyne
  参考文献：
  名称：

  Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones:  Formation of Highly Functionalized Vinyl Triflates

  摘要：

  [GRAPHICS]We describe the synthesis of alpha,alpha-dibromomethyl ynones (8) and their subsequent derivatization to vinyl acetates (10). These vinyl acetates feature a 1,1-dibromo-olefin moiety, which is readily exploited in palladium-catalyzed Sonogashira, Stille, and Suzuki cross-coupling reactions with alkynes, stannanes, and boronic acids, respectively. A novel one-pot process then directly converts the resulting vinyl acetates 11-13 to the vinyl triflate derivatives 14a-j.

  DOI：

  10.1021/ol027267i
• 作为产物：
  描述：

  三乙基氯硅烷 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 三乙胺 为溶剂， 反应 77.0h， 生成 3-acetoxy-1-triethylsilyl-4-triisopropylsilylethynyl-6-triisopropylsilyl-hex-3-en-1,5-diyne
  参考文献：
  名称：

  Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones:  Formation of Highly Functionalized Vinyl Triflates

  摘要：

  [GRAPHICS]We describe the synthesis of alpha,alpha-dibromomethyl ynones (8) and their subsequent derivatization to vinyl acetates (10). These vinyl acetates feature a 1,1-dibromo-olefin moiety, which is readily exploited in palladium-catalyzed Sonogashira, Stille, and Suzuki cross-coupling reactions with alkynes, stannanes, and boronic acids, respectively. A novel one-pot process then directly converts the resulting vinyl acetates 11-13 to the vinyl triflate derivatives 14a-j.

  DOI：

  10.1021/ol027267i