1-(2-allyl-3,6-dimethoxyphenyl)butane-1,4-diol | 1392299-36-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(2-allyl-3,6-dimethoxyphenyl)butane-1,4-diol
• CAS: 1392299-36-3
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: OJROGVXFLLWOBS-UHFFFAOYSA-N

物化性质

• 沸点：
  431.4±45.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-allyl-3,6-dimethoxyphenyl)butane-1,4-diol 在 copper(II) choride dihydrate 、 氧气 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以72%的产率得到3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2,7)]trideca-2,4,6-triene
  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)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