4,4-dimethoxy-5-phenyl-2-cyclohexenone | 119928-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-dimethoxy-5-phenyl-2-cyclohexenone
• 英文别名: 4,4-Dimethoxy-5-phenyl-2-cyclohexen-1-one；4,4-dimethoxy-5-phenylcyclohex-2-en-1-one
• CAS: 119928-00-6
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: LUBDGTSHGZHLJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4,4-dimethoxy-5-phenyl-2-cyclohexenone 在 lithium diisopropyl amide 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以56%的产率得到5,5,5',5'-tetramethoxyl-6,6'-diphenyl-1,1'-bi(cyclohex-3-ene)-2,2'-dione
  参考文献：
  名称：

  Enantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange

  摘要：

  A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF3 center dot OEt2. On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.

  DOI：

  10.1021/ja108717r
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 、 苯基溴化镁 在 甲铝双(2,6-二叔丁基-4-苯甲醚) 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到4,4-dimethoxy-5-phenyl-2-cyclohexenone
  参考文献：
  名称：

  Oxygenophilic organoaluminum-mediated conjugate addition of alkyllithium and Grignard reagents to quinone monoketals and quinol ethers. The directing effect of a methoxy group on the 1,4-addition process

  摘要：

  DOI：

  10.1021/jo00279a033

文献信息

• Oxygenophilic organoaluminium-promoted 1,4-addition of organolithium reagents to quinone monoacetals
  作者：Alan J. Stern、John S. Swenton

  DOI：10.1039/c39880001255

  日期：——

  Complexation of quinone monoacetals with methylaluminium bis-(2,6-di-t-butyl-4-methylphenoxide), followed by addition of organolithium reagents, gives products from 1,4-addition of the organolithium reagent to the quinone monoacetal.

  醌单缩醛与双（2,6-二叔丁基-4-甲基苯氧基）甲基铝的络合，然后加入有机锂试剂，得到有机锂试剂从1,4-加成到醌单缩醛的产物。
• Synthesis of <i>meta</i> -Arylated Phenol Derivatives by Rhodium(I)-Catalyzed Arylation of Quinone Monoacetal
  作者：Jianhang Huang、Na Liu、Tao Lu、Xiaowei Dou

  DOI：10.1002/adsc.201800778

  日期：2018.9.17

  The first selective synthesis of meta‐arylphenol derivatives by arylation of quinone monoacetal is reported. The transformation was achieved under Rh(I) catalysis via a formal arylation/demethoxylation process, and valuable meta‐arylphenols were obtained in high yields under mild conditions. Remarkably, an unprecedented convergent reaction pathway was assumed to be involved.

  据报道，通过醌单缩醛的芳基化首次选择性合成间-芳基苯酚衍生物。在Rh（I）催化下，通过正式的芳基化/脱甲氧基化工艺完成了转化，在温和条件下以高收率获得了有价值的间-芳基苯酚。显着地，假定涉及前所未有的收敛反应途径。
• STERN, ALAN J.;ROHDE, JEFFREY J.;SWENTON, JOHN S., J. ORG. CHEM., 54,(1989) N8, C. 4413-4419
  作者：STERN, ALAN J.、ROHDE, JEFFREY J.、SWENTON, JOHN S.

  DOI：——

  日期：——
• STERN, ALAN J.;SWENTON, JOHN S., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 18, C. 1255-1256
  作者：STERN, ALAN J.、SWENTON, JOHN S.

  DOI：——

  日期：——
• Oxygenophilic organoaluminum-mediated conjugate addition of alkyllithium and Grignard reagents to quinone monoketals and quinol ethers. The directing effect of a methoxy group on the 1,4-addition process
  作者：Alan J. Stern、Jeffrey J. Rohde、John S. Swenton

  DOI：10.1021/jo00279a033

  日期：1989.9