5,5-dimethoxy-4-octanone | 134030-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethoxy-4-octanone
• 英文别名: 5,5-Dimethoxyoctan-4-one
• CAS: 134030-87-8
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: RRDQUQCCZKAPSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethoxy-4-octanone 在 对甲苯磺酸 水 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 4,5-辛二酮
  参考文献：
  名称：

  Selenium-mediated conversion of alkynes into .alpha.-dicarbonyl compounds

  摘要：

  The reaction of terminal and internal alkynes with diphenyl diselenide and ammonium peroxydisulfate in methanol proceeds smoothly to give alpha-keto acetals and alpha-keto ketals, respectively. This one-pot procedure is suggested to proceed through the initial formation of phenylselenenyl sulfate, a strong electrophilic reagent which effects the methoxyselenenylation of the alkynes. The addition products thus formed suffer methoxydeselenenylation giving the observed products and regenerating the phenylselenenylating agent. In some cases the reaction can be carried out using only catalytic amounts of diphenyl diselenide. The same reaction carried out in the presence of water or of ethylene glycol gives the unprotected or the diprotected alpha-dicarbonyl compounds, respectively.

  DOI：

  10.1021/jo00014a038
• 作为产物：
  描述：

  甲醇 、 4-辛炔 在 ammonium persulfate 、 二苯基二硒醚 作用下， 反应 1.5h， 以51%的产率得到5,5-dimethoxy-4-octanone
  参考文献：
  名称：

  Selenium-mediated conversion of alkynes into .alpha.-dicarbonyl compounds

  摘要：

  The reaction of terminal and internal alkynes with diphenyl diselenide and ammonium peroxydisulfate in methanol proceeds smoothly to give alpha-keto acetals and alpha-keto ketals, respectively. This one-pot procedure is suggested to proceed through the initial formation of phenylselenenyl sulfate, a strong electrophilic reagent which effects the methoxyselenenylation of the alkynes. The addition products thus formed suffer methoxydeselenenylation giving the observed products and regenerating the phenylselenenylating agent. In some cases the reaction can be carried out using only catalytic amounts of diphenyl diselenide. The same reaction carried out in the presence of water or of ethylene glycol gives the unprotected or the diprotected alpha-dicarbonyl compounds, respectively.

  DOI：

  10.1021/jo00014a038

文献信息

• Selenium-mediated conversion of alkynes into .alpha.-dicarbonyl compounds
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Donatella Chianelli、Donatella Bartoli

  DOI：10.1021/jo00014a038

  日期：1991.7

  The reaction of terminal and internal alkynes with diphenyl diselenide and ammonium peroxydisulfate in methanol proceeds smoothly to give alpha-keto acetals and alpha-keto ketals, respectively. This one-pot procedure is suggested to proceed through the initial formation of phenylselenenyl sulfate, a strong electrophilic reagent which effects the methoxyselenenylation of the alkynes. The addition products thus formed suffer methoxydeselenenylation giving the observed products and regenerating the phenylselenenylating agent. In some cases the reaction can be carried out using only catalytic amounts of diphenyl diselenide. The same reaction carried out in the presence of water or of ethylene glycol gives the unprotected or the diprotected alpha-dicarbonyl compounds, respectively.