1,1-dibromo-5,5-dimethylhex-1-en-3-yne | 1246055-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dibromo-5,5-dimethylhex-1-en-3-yne
• CAS: 1246055-03-7
• 化学式: C₈H₁₀Br₂
• 分子量: 265.975
• InChiKey: TYFVCKZDEBZFMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,1-dibromo-5,5-dimethylhex-1-en-3-yne 、 N,N-二甲基甲酰胺 在 正丁基锂 、 potassium dihydrogenphosphate 、 水 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 为溶剂， 反应 1.75h， 以53%的产率得到6,6-dimethyl-hepta-2,4-diynal
  参考文献：
  名称：

  Synthesis of Simple Diynals, Diynones, Their Hydrazones, and Diazo Compounds: Precursors to a Family of Dialkynyl Carbenes (R¹—C≡C—C̈—C≡C—R²)

  摘要：

  A variety of substituted pentadiynols, -diynals, and -diynones have been prepared en route to precursors to dialkynyl carbenes (R-1-C C-C-C C-R-2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4 + 1, 3 2, 2 + 2 + 1, and 2 + 1 + 1 + 1 coupling methodologies. The Dess Martin periodinane serves as an excellent method for the oxidation of pentadiynols to diynals and diynones, although many of the oxidized products are sufficiently reactive that they were not isolated; rather, they were generated in situ and intercepted with nucleophiles such as tosylhydrazide or trisylhydrazide. The hydrazone derivatives are generally reliable precursors to diazo compounds and carbenes, although cyclization of the hydrazone to afford a pyrazole can be a complicating factor in certain instances.

  DOI：

  10.1021/jo101125y
• 作为产物：
  描述：

  4,4-二甲基-2-戊炔醛 、 四溴化碳 在 三苯基膦 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以81%的产率得到1,1-dibromo-5,5-dimethylhex-1-en-3-yne
  参考文献：
  名称：

  Synthesis of Simple Diynals, Diynones, Their Hydrazones, and Diazo Compounds: Precursors to a Family of Dialkynyl Carbenes (R¹—C≡C—C̈—C≡C—R²)

  摘要：

  A variety of substituted pentadiynols, -diynals, and -diynones have been prepared en route to precursors to dialkynyl carbenes (R-1-C C-C-C C-R-2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4 + 1, 3 2, 2 + 2 + 1, and 2 + 1 + 1 + 1 coupling methodologies. The Dess Martin periodinane serves as an excellent method for the oxidation of pentadiynols to diynals and diynones, although many of the oxidized products are sufficiently reactive that they were not isolated; rather, they were generated in situ and intercepted with nucleophiles such as tosylhydrazide or trisylhydrazide. The hydrazone derivatives are generally reliable precursors to diazo compounds and carbenes, although cyclization of the hydrazone to afford a pyrazole can be a complicating factor in certain instances.

  DOI：

  10.1021/jo101125y