3,5-己二炔-2-酮 | 31097-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,5-己二炔-2-酮
• 英文名称: hexa-3,5-diyn-2-one
• 英文别名: 3,5-Hexadiyn-2-one
• CAS: 31097-80-0
• 化学式: C₆H₄O
• 分子量: 92.0972
• InChiKey: GCZFLFFXKMSZRU-UHFFFAOYSA-N

物化性质

• 沸点：
  133.4±23.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  3,5-己二炔-2-酮 、 对甲苯磺酰肼 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 以490 mg的产率得到anti-hexa-3,5-diyn-2-one tosylhydrazone
  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：

  Hexadiin-(3.5)-ol-(2) 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,5-己二炔-2-酮
  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

文献信息

• Synthesis of Simple Diynals, Diynones, Their Hydrazones, and Diazo Compounds: Precursors to a Family of Dialkynyl Carbenes (R¹—C≡C—C̈—C≡C—R²)
  作者：Nathan P. Bowling、Nicola J. Burrmann、Robert J. Halter、Jonathan A. Hodges、Robert J. McMahon

  DOI：10.1021/jo101125y

  日期：2010.10.1

  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.