1-[2-hydroxy-6-(methoxymethoxy)-4-pyrrolidin-1-ylphenyl]ethanone | 1400466-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-hydroxy-6-(methoxymethoxy)-4-pyrrolidin-1-ylphenyl]ethanone
• CAS: 1400466-50-3
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: VLMJWTWTJJEYQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-6-(methoxymethoxy)-4-pyrrolidin-1-ylphenyl]ethanone 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.08h， 生成 (2Z)-2-(4-methoxybenzylidene)-4-(methoxymethoxy)-6-pyrrolidin-1-yl-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin

  摘要：

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.

  DOI：

  10.1055/s-0031-1291153
• 作为产物：
  描述：

  氯甲基甲基醚 、 1-(2,6-二羟基-4-吡咯烷-1-基苯基)乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以62%的产率得到1-[2-hydroxy-6-(methoxymethoxy)-4-pyrrolidin-1-ylphenyl]ethanone
  参考文献：
  名称：

  A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin

  摘要：

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.

  DOI：

  10.1055/s-0031-1291153