6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid | 1132774-47-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid
• 英文别名: 6,8-Di-t-butyl-2-oxo-3,4-dihydro-2h-chromen-4-ylacetic acid；2-(6,8-ditert-butyl-2-oxo-3,4-dihydrochromen-4-yl)acetic acid
• CAS: 1132774-47-0
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: LSDIMBMWSRQETM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二酸 、 3,5-二叔丁基水杨醛 在 哌啶 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以51%的产率得到6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid
  参考文献：
  名称：

  Anionic condensations of 3,5-di-tert-butyl-4(2)-hydroxybenzaldehydes in the presence of weak bases

  摘要：

  Products of the reactions of 4- and 2-hydroxy-3,5-di-tert-butyl-benzaldehydes with malonic acid, diethyl malonate, and acetic anhydride in the presence of weak bases were isolated and identified. The reactions of 3,5-di-tert-butyl-4-hydroxybenzaldehyde with malonic acid and acetic anhydride in the presence of sodium acetate and piperidine gave 3,5-di-tert-butyl-4-hydroxycinnamic acid. The reaction of its 2-hydroxy isomer with acetic anhydride stopped at the stage of formation of the corresponding O-acetyl derivative, while in the reaction with malonic acid the corresponding substituted cinnamic acid and its lactone (coumarin derivative) were formed as intermediate products in a transformation sequence finally leading to 3-(3,5-di-tertbutyl-2-hydroxyphenyl)-3-piperidinopropionic acid and 6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid. Analogous differences were typical of reactions of isomeric 4- and 2-hydroxy-3,5-di-tert-butylbenzaldehydes with diethyl malonate. The transformations of the 2-hydroxy isomer were accompanied by hydrolysis and formation of an adduct of intermediate coumarin derivative with diethyl malonate and piperidine.

  DOI：

  10.1134/s1070428008060043