3-(3,5-di-tert-butyl-2-hydroxyphenyl)-3-piperidinopropionic acid | 1132774-48-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(3,5-di-tert-butyl-2-hydroxyphenyl)-3-piperidinopropionic acid
• 英文别名: 3-(3,5-Di-tertbutyl-2-hydroxyphenyl)-3-piperidinopropionic acid；3-(3,5-ditert-butyl-2-hydroxyphenyl)-3-piperidin-1-ylpropanoic acid
• CAS: 1132774-48-1
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: IYJKNQMTPOIKED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶 、 丙二酸 、 3,5-二叔丁基水杨醛 以 吡啶 为溶剂， 反应 3.0h， 以19%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