3,4-dimethoxy-2-hydroxybenzaldehyde oxime | 917955-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,4-dimethoxy-2-hydroxybenzaldehyde oxime
• 英文别名: 6-(Hydroxyiminomethyl)-2,3-dimethoxyphenol
• CAS: 917955-26-1
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: QINSZVGYJIMLJX-UHFFFAOYSA-N

物化性质

• 熔点：
  111.5-112 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  327.2±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-2-hydroxybenzaldehyde oxime 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 3,4-dimethoxy-2-hydroxybenzonitrile
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of Organ-Specific Iron Chelators

  摘要：

  A series of iron chelators, three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid (DADFT) and three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic acid (DADMDFT) analogues are synthesized and assessed for their lipophilicity (log Papp), iron-clearing efficiency (ICE) in rodents and iron-loaded primates (Cebus apella), toxicity in rodents, and organ distribution in rodents. The results lead to a number of generalizations useful in chelator design strategies. In rodents, while log Papp is a good predictor of a chelator's ICE, chelator liver concentration is a better tool. In primates, log Papp is a good predictor of ICE, but only when comparing structurally very similar chelators. There is a profound difference in toxicity between the DADMDFT and DADFT series: DADMDFTs are less toxic. Within the DADFT family of ligands, the more lipophilic ligands are generally more toxic. Lipophilicity can have a profound effect on ligand organ distribution, and ligands can thus be targeted to organs compromised in iron overload disease, for example, the heart.

  DOI：

  10.1021/jm0608816
• 作为产物：
  描述：

  3,4-二甲氧基-2-羟基苯甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到3,4-dimethoxy-2-hydroxybenzaldehyde oxime
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of Organ-Specific Iron Chelators

  摘要：

  A series of iron chelators, three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid (DADFT) and three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic acid (DADMDFT) analogues are synthesized and assessed for their lipophilicity (log Papp), iron-clearing efficiency (ICE) in rodents and iron-loaded primates (Cebus apella), toxicity in rodents, and organ distribution in rodents. The results lead to a number of generalizations useful in chelator design strategies. In rodents, while log Papp is a good predictor of a chelator's ICE, chelator liver concentration is a better tool. In primates, log Papp is a good predictor of ICE, but only when comparing structurally very similar chelators. There is a profound difference in toxicity between the DADMDFT and DADFT series: DADMDFTs are less toxic. Within the DADFT family of ligands, the more lipophilic ligands are generally more toxic. Lipophilicity can have a profound effect on ligand organ distribution, and ligands can thus be targeted to organs compromised in iron overload disease, for example, the heart.

  DOI：

  10.1021/jm0608816