1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one | 1392299-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one
• 英文别名: 1-(3,6-Dimethoxy-2-prop-2-enylphenyl)-3,4-dihydroxybutan-1-one
• CAS: 1392299-35-2
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: CVJWWMUMRXBMTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到1-(2-allyl-3,6-dimethoxyphenyl)butane-1,4-diol
  参考文献：
  名称：

  Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin

  摘要：

  Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlH4 resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlH4 and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2.7)]trideca-2,4,6-trien-11-yl)methanol, the core of marticin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.052
• 作为产物：
  描述：

  1-(2-烯丙基-3,6-二羟基苯基)乙烷-1-酮 在 lithium aluminium tetrahydride 、 sodium ethanolate 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.0h， 生成 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one
  参考文献：
  名称：

  Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin

  摘要：

  Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlH4 resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlH4 and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2.7)]trideca-2,4,6-trien-11-yl)methanol, the core of marticin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.052

文献信息

• Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin
  作者：Adushan Pillay、Amanda L. Rousseau、Manuel A. Fernandes、Charles B. de Koning

  DOI：10.1016/j.tet.2012.06.052

  日期：2012.9

  Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlH4 resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlH4 and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2.7)]trideca-2,4,6-trien-11-yl)methanol, the core of marticin. (C) 2012 Elsevier Ltd. All rights reserved.