4-(3-甲基-4-甲氧基苯基)-2-丁烯酸乙酯 | 122333-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(3-甲基-4-甲氧基苯基)-2-丁烯酸乙酯
• 英文名称: ethyl 4-(3-methyl-4-methoxyphenyl)-2-butenoate
• 英文别名: Ethyl 4-(4-methoxy-3-methylphenyl)-2-butenoate；ethyl 4-(4-methoxy-3-methylphenyl)but-2-enoate
• CAS: 122333-99-7
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: LSACZUUOCIFZDL-UHFFFAOYSA-N

物化性质

• 沸点：
  336.0±30.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(3-甲基-4-甲氧基苯基)-2-丁烯酸乙酯 在 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 甲烷磺酸 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 25.0 ℃ 、379.21 kPa 条件下， 反应 17.0h， 生成 1,2,3,4-tetrahydro-6-methyl-7-methoxy-1-naphthalenol
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029
• 作为产物：
  描述：

  4-甲氧基-3-甲基苯甲醛 在 水 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 4-(3-甲基-4-甲氧基苯基)-2-丁烯酸乙酯
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029