1,1-dibromo-4-triethylsilyl-but-2-one-3-yne | 500297-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dibromo-4-triethylsilyl-but-2-one-3-yne
• 英文别名: 1,1-Dibromo-4-triethylsilylbut-3-yn-2-one
• CAS: 500297-72-3
• 化学式: C₁₀H₁₆Br₂OSi
• 分子量: 340.13
• InChiKey: USYPNNSXLZMFHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-dibromo-4-triethylsilyl-but-2-one-3-yne 在 四(三苯基膦)钯 甲基锂 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 17.83h， 生成 1-(diphenylmethylene)-3-(triethylsilyl)-2-propynyl trifluoromethane sulfonate
  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 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 1,1-dibromo-4-triethylsilyl-but-2-one-3-yne
  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

文献信息

• Synthesis and Derivatization of Ethynyl α,α-Dibromomethyl Ketones:  Formation of Highly Functionalized Vinyl Triflates
  作者：Trent Rankin、Rik R. Tykwinski

  DOI：10.1021/ol027267i

  日期：2003.1.1

  [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.