4-Methoxy-2,6,6-trimethylcyclohexa-2,4-dien-1-one | 88563-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Methoxy-2,6,6-trimethylcyclohexa-2,4-dien-1-one
• CAS: 88563-60-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: AVRPPMLLJZHKKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6,6-三甲基-2-环己烯-1,4-二酮 、 原甲酸三甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 以95%的产率得到4-Methoxy-2,6,6-trimethylcyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  Asymmetrische katalysen

  摘要：

  Enantioselective hydrogenation of 4-oxoisophorone 1. catalysed by BINAP-Ru(II) complexes, gives the corresponding saturated diketone 2 in 80% chemical yield and 50% enantiomeric excess. By repeated crystallisation from petroleum ether/dichloromethane 4/1 the diketone 2 is obtained optically pure in 25% total yield. The monoalcohol 3 is formed as a byproduct of the hydrogenation. The formation of 3 can be suppressed by using the monomethyl-enol ether 4 as a substrate. Catalytic hydrogenation of 4 in methanol gives exclusively the dimethylketal 5, which upon acidic hydrolysis is transformed into the diketone 2 in 50% ee.

  DOI：

  10.1016/0022-328x(93)83319-q

文献信息

• TANG, PENG-CHO;WULFF, W. D., J. AMER. CHEM. SOC., 1984, 106, N 4, 1132-1133
  作者：TANG, PENG-CHO、WULFF, W. D.

  DOI：——

  日期：——
• Asymmetrische katalysen
  作者：Henri Brunner、Konrad Fisch

  DOI：10.1016/0022-328x(93)83319-q

  日期：1993.8

  Enantioselective hydrogenation of 4-oxoisophorone 1. catalysed by BINAP-Ru(II) complexes, gives the corresponding saturated diketone 2 in 80% chemical yield and 50% enantiomeric excess. By repeated crystallisation from petroleum ether/dichloromethane 4/1 the diketone 2 is obtained optically pure in 25% total yield. The monoalcohol 3 is formed as a byproduct of the hydrogenation. The formation of 3 can be suppressed by using the monomethyl-enol ether 4 as a substrate. Catalytic hydrogenation of 4 in methanol gives exclusively the dimethylketal 5, which upon acidic hydrolysis is transformed into the diketone 2 in 50% ee.