4-O-methoxyethoxymethyl-vanillazide | 875153-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-O-methoxyethoxymethyl-vanillazide
• 英文别名: 4-(Azidomethyl)-2-methoxy-1-(2-methoxyethoxymethoxy)benzene
• CAS: 875153-10-9
• 化学式: C₁₂H₁₇N₃O₄
• 分子量: 267.285
• InChiKey: MDCRTDSVLDGLOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-O-methoxyethoxymethyl-vanillazide 在 锌 氢溴酸 、 碘 、 silver trifluoroacetate 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 3.0h， 生成 6-iodovanillamine
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q
• 作为产物：
  描述：

  3-methoxy-4-<2'-(methoxyethoxy)methoxy>-benzaldehyde 在 sodium tetrahydroborate 、 二苯基磷酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 4-O-methoxyethoxymethyl-vanillazide
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q