diacetylvanillylmandelic acid | 97412-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: diacetylvanillylmandelic acid
• 英文别名: acetoxy-(4-acetoxy-3-methoxy-phenyl)-acetic acid；Acetoxy-(4-acetoxy-3-methoxy-phenyl)-essigsaeure；Carboxyvanillyl alcohol diacetate；2-acetyloxy-2-(4-acetyloxy-3-methoxyphenyl)acetic acid
• CAS: 97412-19-6
• 化学式: C₁₃H₁₄O₇
• 分子量: 282.25
• InChiKey: BORJCACESSSLKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diacetylvanillylmandelic acid 在 氯化亚砜 、 乙醚 、 溶剂黄146 、 苯 作用下， 生成 1,3-diacetoxy-1-(4-acetoxy-3-methoxy-phenyl)-acetone
  参考文献：
  名称：

  Studies on Lignin and Related Compounds. LXXXII. Synthesis and Properties of 1,3-Diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and 1-Acetoxy-3-chloro-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and their Relation to Lignin Structure¹

  摘要：

  DOI：

  10.1021/ja01232a029
• 作为产物：
  描述：

  香草基扁桃酸乙酯 在 吡啶 、 sodium hydroxide 作用下， 生成 diacetylvanillylmandelic acid
  参考文献：
  名称：

  Studies on Lignin and Related Compounds. LXXXII. Synthesis and Properties of 1,3-Diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and 1-Acetoxy-3-chloro-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and their Relation to Lignin Structure¹

  摘要：

  DOI：

  10.1021/ja01232a029

文献信息

• Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"
  作者：Christopher S. J. Walpole、Roger Wrigglesworth、Stuart Bevan、Elizabeth A. Campbell、Andy Dray、Iain F. James、Kay J. Masdin、Martin N. Perkins、Janet Winter

  DOI：10.1021/jm00068a016

  日期：1993.8

  Structural variants of the hydrophobic side chain (''C region'') of the capsaicin molecule have been incorporated into a series of vanillylamides and vanillylthioureas. These compounds have been tested in an in vitro assay for agonism (Ca-45(2+) influx into dorsal root ganglia neurones), previously shown to be predictive of analgesic activity. The results of this study have established the requirement for a hydrophobic substituent of limited size (molar refractivity, MR, <55) in order to obtain high potency. Combination of the information gained here about the ''C-region'' of the capsaicin molecule with the studies described in the preceding two papers provides a rational basis for the design of compounds of increased potency.
• Studies on Lignin and Related Compounds. LXXXII. Synthesis and Properties of 1,3-Diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and 1-Acetoxy-3-chloro-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and their Relation to Lignin Structure¹
  作者：J. A. F. Gardner、Harold Hibbert

  DOI：10.1021/ja01232a029

  日期：1944.4