1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one
• 英文别名: (E)-1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: AOIPIPNOUYOGLM-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one 在 phase-transfer catalyst 双氧水 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis of Lignin Models of beta-5 Type.

  摘要：

  A beta-5 lignin model of the phenylcoumaran type, trans-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo [b]furan, was prepared by acid-catalysed cyclization of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-1,3-propanediol. The cyclization was accomplished by treatment with 0.2 M HCl in dioxane-water (1:1) at 50 degrees C. The reaction was first order with respect to the substrate (tau(1/2) 36 min). 1-( 3,4-Dimethoxyphenyl)-2-( 2-hydroxy-3-methoxyphenyl )-1,3-propanediol, which is a model compound representative of a second type of lignin structure of beta-5 type, was in turn obtained by synthesis starting from o-vanillin and 3',4'-dimethoxyacetophenone. In the first step equimolar amounts of these compounds were treated with alkali to give 1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one. Conversion of this compound into its tetrahydropyran-2-yl ether and subsequent epoxidation gave 1-(3,4-dimethoxyphenyl)-3-[3-methoxy-2-(tetrahydropyran-2-yloxy)phenyl]-2,3-epoxypropanone. Acid-catalysed (boron trifluoride) rearrangement of this compound (the tetrahydropyran-2-yl group was removed simultaneously), reduction of the resulting product with sodium borohydride and subsequent chromatographic purification gave a mixture of the erythro and threo forms of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl )-1,3-propanediol (yield, 57%). The erythro form predominated in the mixture and could be isolated by fractional crystallization. Separation of the diastereomers could be accomplished by ion exchange chromatography.

  DOI：

  10.3891/acta.chem.scand.51-1224
• 作为产物：
  描述：

  邻香草醛 、 3,4-二甲氧基苯乙酮 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以75%的产率得到1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Synthesis of Lignin Models of beta-5 Type.

  摘要：

  A beta-5 lignin model of the phenylcoumaran type, trans-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo [b]furan, was prepared by acid-catalysed cyclization of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-1,3-propanediol. The cyclization was accomplished by treatment with 0.2 M HCl in dioxane-water (1:1) at 50 degrees C. The reaction was first order with respect to the substrate (tau(1/2) 36 min). 1-( 3,4-Dimethoxyphenyl)-2-( 2-hydroxy-3-methoxyphenyl )-1,3-propanediol, which is a model compound representative of a second type of lignin structure of beta-5 type, was in turn obtained by synthesis starting from o-vanillin and 3',4'-dimethoxyacetophenone. In the first step equimolar amounts of these compounds were treated with alkali to give 1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one. Conversion of this compound into its tetrahydropyran-2-yl ether and subsequent epoxidation gave 1-(3,4-dimethoxyphenyl)-3-[3-methoxy-2-(tetrahydropyran-2-yloxy)phenyl]-2,3-epoxypropanone. Acid-catalysed (boron trifluoride) rearrangement of this compound (the tetrahydropyran-2-yl group was removed simultaneously), reduction of the resulting product with sodium borohydride and subsequent chromatographic purification gave a mixture of the erythro and threo forms of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl )-1,3-propanediol (yield, 57%). The erythro form predominated in the mixture and could be isolated by fractional crystallization. Separation of the diastereomers could be accomplished by ion exchange chromatography.

  DOI：

  10.3891/acta.chem.scand.51-1224

文献信息

• Synthesis of Lignin Models of beta-5 Type.
  作者：Shiming Li、Knut Lundquist、Kjetil Holm、Lars Skattebøl、Connie N. Rosendahl

  DOI：10.3891/acta.chem.scand.51-1224

  日期：——

  A beta-5 lignin model of the phenylcoumaran type, trans-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo [b]furan, was prepared by acid-catalysed cyclization of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl)-1,3-propanediol. The cyclization was accomplished by treatment with 0.2 M HCl in dioxane-water (1:1) at 50 degrees C. The reaction was first order with respect to the substrate (tau(1/2) 36 min). 1-( 3,4-Dimethoxyphenyl)-2-( 2-hydroxy-3-methoxyphenyl )-1,3-propanediol, which is a model compound representative of a second type of lignin structure of beta-5 type, was in turn obtained by synthesis starting from o-vanillin and 3',4'-dimethoxyacetophenone. In the first step equimolar amounts of these compounds were treated with alkali to give 1-(3,4-dimethoxyphenyl)-3-(2-hydroxy-3-methoxyphenyl)-2-propen-1-one. Conversion of this compound into its tetrahydropyran-2-yl ether and subsequent epoxidation gave 1-(3,4-dimethoxyphenyl)-3-[3-methoxy-2-(tetrahydropyran-2-yloxy)phenyl]-2,3-epoxypropanone. Acid-catalysed (boron trifluoride) rearrangement of this compound (the tetrahydropyran-2-yl group was removed simultaneously), reduction of the resulting product with sodium borohydride and subsequent chromatographic purification gave a mixture of the erythro and threo forms of 1-(3,4-dimethoxyphenyl)-2-(2-hydroxy-3-methoxyphenyl )-1,3-propanediol (yield, 57%). The erythro form predominated in the mixture and could be isolated by fractional crystallization. Separation of the diastereomers could be accomplished by ion exchange chromatography.