1-(4-hydroxy-3-methoxyphenyl)-1-hydroxyundecane | 150059-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)-1-hydroxyundecane
• 英文别名: 4-(1-Hydroxyundecyl)-2-methoxyphenol
• CAS: 150059-17-9
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: DPHCMXDNSDOMGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxy-3-methoxyphenyl)-1-hydroxyundecane 在 sodium hydrogen sulfate 作用下， 以 xylene 为溶剂， 反应 2.0h， 以75%的产率得到1-(4-hydroxy-3-methoxyphenyl)undec-1-ene
  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：

  Decylmagnesium bromide 、 香草醛 在 六甲基二硅氮烷 作用下， 生成 1-(4-hydroxy-3-methoxyphenyl)-1-hydroxyundecane
  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