ethyl 3-(2,4-dihydroxy-5-methoxyphenyl)propionate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 3-(2,4-dihydroxy-5-methoxyphenyl)propionate
• 英文别名: Ethyl 3-(2,4-dihydroxy-5-methoxyphenyl)propanoate；ethyl 3-(2,4-dihydroxy-5-methoxyphenyl)propanoate
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: VGWRIVSOTKCEMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  东莨菪内酯 、 乙醇 在 palladium on activated charcoal 氢气 作用下， 50.0 ℃ 、344.74 kPa 条件下， 反应 7.0h， 以80%的产率得到ethyl 3-(2,4-dihydroxy-5-methoxyphenyl)propionate
  参考文献：
  名称：

  Synthesis of 6-methoxy-4H-1-benzopyran-7-ol, a character donating component of the fragrance of Wisteria sinensis

  摘要：

  6-Methoxy-4H-1-benzopyran-7-ol 7, a major impact flavor compound of Wisteria sinensis has been synthesized from 2,4,5-trimethoxybenzaldehyde 1 via scopoletin 3. The synthetic sequence comprised (i) bisdemethylation of 2,4,5-timethoxybenzaldehyde 1, (ii) Wittig reaction with ethoxycarbonylmethylenetriphenylphosphorane, (iii) hydrogenation on palladium/carbon in glacial acetic acid, (iv) DIBAL-H reduction of the intermediate lactone and (v) dehydration of the lactol with anhydrous oxalic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00081-9

文献信息

• Synthesis of 6-methoxy-4H-1-benzopyran-7-ol, a character donating component of the fragrance of Wisteria sinensis
  作者：Jan Demyttenaere、Kris Van Syngel、A Peter Markusse、Stijn Vervisch、Silvia Debenedetti、Norbert De Kimpe

  DOI：10.1016/s0040-4020(02)00081-9

  日期：2002.3

  6-Methoxy-4H-1-benzopyran-7-ol 7, a major impact flavor compound of Wisteria sinensis has been synthesized from 2,4,5-trimethoxybenzaldehyde 1 via scopoletin 3. The synthetic sequence comprised (i) bisdemethylation of 2,4,5-timethoxybenzaldehyde 1, (ii) Wittig reaction with ethoxycarbonylmethylenetriphenylphosphorane, (iii) hydrogenation on palladium/carbon in glacial acetic acid, (iv) DIBAL-H reduction of the intermediate lactone and (v) dehydration of the lactol with anhydrous oxalic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.