4-[(1S,2S)-2-甲基-6-氧代环己基]苯甲酸乙酯 | 824390-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(1S,2S)-2-甲基-6-氧代环己基]苯甲酸乙酯
• 英文名称: 4-(2-methyl-6-oxo-cyclohexyl)benzoic acid ethyl ester
• 英文别名: ethyl 4-[(1S,2S)-2-methyl-6-oxocyclohexyl]benzoate
• CAS: 824390-81-0
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: QEBRHQZSZTWLEJ-NHYWBVRUSA-N

物化性质

• 熔点：
  108-110 °C
• 沸点：
  389.9±42.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2-环己烯-1-酮 、 4-溴苯甲酸乙酯 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 4-(2-methyl-6-oxo-cyclohexyl)benzoic acid ethyl ester 、 4-(2-methyl-6-oxo-cyclohexyl)benzoic acid ethyl ester 、 4-(2-methyl-6-oxo-cyclohexyl)benzoic acid ethyl ester 、 4-[(1S,2S)-2-甲基-6-氧代环己基]苯甲酸乙酯
  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.