2-Formyl-4-methylphenylacetic Acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Formyl-4-methylphenylacetic Acid
• 英文别名: (2-Formyl-4-methyl-phenyl)-acetic acid；2-(2-formyl-4-methylphenyl)acetic acid
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: MSWSZUNCYLRAIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二甲基苯甲醛 在 盐酸 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 对甲苯磺酸 作用下， 反应 4.0h， 生成 2-Formyl-4-methylphenylacetic Acid
  参考文献：
  名称：

  Directed metalation of aromatic aldimines with lithium 2,2,6,6-tetramethylpiperidide

  摘要：

  N-Cyclohexyl aromatic aldimines are ortho-lithiated or o-methyl-lithiated with 2 equiv of lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF solution it -15-degrees-C. The lithiated intermediates generally reacted with alkyl halides or CO2 to provide ortho- functionalized aldimine products which could be readily converted to the corresponding aldehydes by hydrolysis with aqueous 4 M HCI. Aromatic aldimines derived from (+/-)-trans-2-methylcyclohexylamine or 3-amino-2,4-dimethylpentane are resistant toward C=N addition with 1 equiv of n-BuLi at 0-degrees-C in THF solution; however, they are also surprisingly resistant toward directed metalation reactions with either LTMP or n-BuLi. Exceptions to the ortho-directing and o-methyl-directing effects of the aldimine group were observed in a reaction of 3-methylthiophene-2-carboxaldehyde cyclohexylimine (7) with LTMP, followed by CH3I, which gave a 9:1 mixture of 3,5-dimethylthiophene-2-carboxaldehyde cyclohexylimine (22) and 5-ethyl-3-methylthiophene-2-carboxaldehyde cyclohexylimine (23), and a reaction of p-tolualdehyde 2,4-dimethylpent-3-ylimine (11) with either n-BuLi or LTMP, followed by CH3I, which gave p-ethylbenzaldehyde 2,4-dimethylpent-3-ylimine (25).

  DOI：

  10.1021/jo00061a020