3-methoxy-4-(nonanoyloxy)benzyl nonanoate | 150058-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-methoxy-4-(nonanoyloxy)benzyl nonanoate
• 英文别名: (3-methoxy-4-nonanoyloxyphenyl)methyl nonanoate
• CAS: 150058-95-0
• 化学式: C₂₆H₄₂O₅
• 分子量: 434.616
• InChiKey: NKIJLIRWPOHKBX-UHFFFAOYSA-N

物化性质

• 沸点：
  502.2±40.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  31.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-(nonanoyloxy)benzyl nonanoate 在 四氢吡咯 作用下， 以49%的产率得到壬酸香草酯
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"

  摘要：

  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.

  DOI：

  10.1021/jm00068a016
• 作为产物：
  描述：

  壬酰氯 、 4-羟基-3-甲氧基苄醇 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以40.5%的产率得到3-methoxy-4-(nonanoyloxy)benzyl nonanoate
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region"

  摘要：

  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.

  DOI：

  10.1021/jm00068a016

文献信息

• Chemoselective Esterification of Phenolic Acids and Alcohols
  作者：Giovanni Appendino、Alberto Minassi、Nives Daddario、Federica Bianchi、Gian Cesare Tron

  DOI：10.1021/ol0266471

  日期：2002.10.1

  [formula: see text] The Mitsunobu reaction can distinguish between alcohol and phenol hydroxyls in esterification reactions, providing an expeditious and broadly applicable entry into various phenolics and polyphenolics of biomedical and nutritional relevance.

  Mitsunobu反应可以区分酯化反应中的醇羟基和酚羟基，为生物医学和营养相关的各种酚类和多酚类化合物提供了快速而广泛适用的入口。