6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal | 144180-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal
• 英文别名: 6-(3,5-Dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)hexanal
• CAS: 144180-82-5
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: AEQBKCQZWQZABT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 生成 (1S*,2S*)- and (1R*,2S*)-2-(3,5-dimethyl-4-hydroxyphenyl)cyclohexanol
  参考文献：
  名称：

  Reductive cyclization of quinone methides

  摘要：

  The first use of reduced quinone methides for the formation of carbon-carbon bonds in cyclization reactions is described. Treatment of quinone methides with SmI2 resulted in intramolecular reaction with internal activated multiple bonds to afford 5- and 6-membered carbocycles in good yields. The activated multiple bonds used are aldehydes and alpha,beta-unsaturated esters and nitriles.

  DOI：

  10.1021/jo00051a038
• 作为产物：
  描述：

  (4-溴-2,6-二甲基苯氧基)(叔丁基)二甲基硅烷 在 palladium on activated charcoal 草酰氯 、 四丁基氟化铵 、 氢气 、 叔丁基锂 、 二甲基亚砜 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醇 、 氘代苯 为溶剂， -78.0~65.0 ℃ 、101.33 kPa 条件下， 反应 25.25h， 生成 6-(3,5-Dimethyl-4-oxo-cyclohexa-2,5-dienylidene)-hexanal
  参考文献：
  名称：

  Reductive cyclization of quinone methides

  摘要：

  The first use of reduced quinone methides for the formation of carbon-carbon bonds in cyclization reactions is described. Treatment of quinone methides with SmI2 resulted in intramolecular reaction with internal activated multiple bonds to afford 5- and 6-membered carbocycles in good yields. The activated multiple bonds used are aldehydes and alpha,beta-unsaturated esters and nitriles.

  DOI：

  10.1021/jo00051a038

文献信息

• Reductive cyclization of quinone methides
  作者：Steven R. Angle、Jon D. Rainier

  DOI：10.1021/jo00051a038

  日期：1992.12

  The first use of reduced quinone methides for the formation of carbon-carbon bonds in cyclization reactions is described. Treatment of quinone methides with SmI2 resulted in intramolecular reaction with internal activated multiple bonds to afford 5- and 6-membered carbocycles in good yields. The activated multiple bonds used are aldehydes and alpha,beta-unsaturated esters and nitriles.