7-Benzyloxy-2-methyl-chroman-2-carboxylic acid ethyl ester | 406488-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-Benzyloxy-2-methyl-chroman-2-carboxylic acid ethyl ester
• CAS: 406488-82-2
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: AWJOYDGVHRWDTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-Benzyloxy-2-methyl-chroman-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 、 caesium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、344.74 kPa 条件下， 反应 5.0h， 生成
  参考文献：
  名称：

  (2R)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents

  摘要：

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-{3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.

  DOI：

  10.1021/jm030621d
• 作为产物：
  描述：

  ethyl 7-hydroxychromane-2-carboxylate 在 六甲基磷酰三胺 、 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 61.0h， 生成 7-Benzyloxy-2-methyl-chroman-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  (2R)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents

  摘要：

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-{3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.

  DOI：

  10.1021/jm030621d