2-(3,5-dimethylphenyl)-3-methyl-cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-dimethylphenyl)-3-methyl-cyclohexanone
• 英文别名: (2S,3S)-2-(3,5-dimethylphenyl)-3-methylcyclohexan-1-one
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: QDANHSYYCARJKT-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基-2-环己烯-1-酮 、 3,5-二甲基溴苯 在 copper(l) chloride 、 palladium diacetate 二苯基硅烷 、 (+)-(S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) 、 sodium t-butanolate 、 cesium fluoride 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 18.0h， 生成 2-(3,5-dimethylphenyl)-3-methyl-cyclohexanone 、 2-(3,5-dimethylphenyl)-3-methyl-cyclohexanone 、 2-(3,5-dimethylphenyl)-3-methyl-cyclohexanone 、 2-(3,5-dimethylphenyl)-3-methyl-cyclohexanone
  参考文献：
  名称：

  One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers

  摘要：

  {graphic} Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.

  DOI：

  10.1021/ol048313c

文献信息

• One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers
  作者：Junghyun Chae、Jaesook Yun、Stephen L. Buchwald

  DOI：10.1021/ol048313c

  日期：2004.12.1

  graphic} Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.