2-methoxy-3-methylcinnamic acid | 74098-89-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-methoxy-3-methylcinnamic acid
• 英文别名: 3-(2-methoxy-3-methylphenyl)prop-2-enoic acid
• CAS: 74098-89-8
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: IMYNKAKBGQJBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-methylcinnamic acid 在 palladium on activated charcoal sodium tetrahydroborate 、 硫酸 、 氢气 、 sodium hydride 、 三氟乙酸酐 作用下， 以 甲醇 、 乙醇 、 水 、 苯 为溶剂， 25.0~70.0 ℃ 、379.21 kPa 条件下， 反应 68.5h， 生成 2-(methylamino)-5-methoxy-6-methyltetralin
  参考文献：
  名称：

  Derivatives of 5-hydroxy-6-methyl-2-aminotetralin

  摘要：

  The title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation. A sequence leading to a key synthetic intermediate, 5-methoxy-6-methyl-2-tetralone, has been developed. In animal test models for dopamine-like effects, the title compounds demonstrated qualitative and quantitative differences from the isomeric 5-methyl-6-hydroxy-2-aminotetralins and from 5,6-dihydroxy-2-aminotetralins. Two of the compounds were potent in a cat cardioaccelerator nerve assay, which involves dopamine receptors.

  DOI：

  10.1021/jm00181a010
• 作为产物：
  描述：

  methyl 2-methoxy-3-methylbenzoate 在 哌啶 、 吡啶 、 potassium hypochlorite 、 苄基三丁基氯化铵 、 红铝 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 6.4h， 生成 2-methoxy-3-methylcinnamic acid
  参考文献：
  名称：

  Derivatives of 5-hydroxy-6-methyl-2-aminotetralin

  摘要：

  The title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation. A sequence leading to a key synthetic intermediate, 5-methoxy-6-methyl-2-tetralone, has been developed. In animal test models for dopamine-like effects, the title compounds demonstrated qualitative and quantitative differences from the isomeric 5-methyl-6-hydroxy-2-aminotetralins and from 5,6-dihydroxy-2-aminotetralins. Two of the compounds were potent in a cat cardioaccelerator nerve assay, which involves dopamine receptors.

  DOI：

  10.1021/jm00181a010

文献信息

• THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：LES LABORATOIRES SERVIER

  公开号：US20150175623A1

  公开（公告）日：2015-06-25

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 12 , X, A and n are as defined in the description. Medicinal products containing the same which are useful in treating pathologies involving a deficit in apoptosis, such as cancer, auto-immune diseases, and diseases of the immune system.

  式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如说明中所述。含有该化合物的药物可用于治疗涉及凋亡缺陷的病理学，如癌症、自身免疫性疾病和免疫系统疾病。
• Thienopyrimidine derivatives, a process for their preparation and pharmaceutical compositions containing them
  申请人：LES LABORATOIRES SERVIER

  公开号：US10278972B2

  公开（公告）日：2019-05-07

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description. Medicinal products containing the same which are useful in treating pathologies involving a deficit in apoptosis, such as cancer, auto-immune diseases, and diseases of the immune system.

  式(I)化合物： 其中 R1、R2、R3、R4、R5、R6、R7、R12、X、A 和 n 如说明中所定义。 含有相同成分的药物产品，可用于治疗涉及细胞凋亡缺陷的病症，如癌症、自身免疫性疾病和免疫系统疾病。
• New thienopyrimidine derivatives, a process for their preparation and pharmaceutical compositions containing them
  申请人：Les Laboratoires Servier

  公开号：EP2886545B1

  公开（公告）日：2016-06-29
• US9670227B2
  申请人：——

  公开号：US9670227B2

  公开（公告）日：2017-06-06
• Derivatives of 5-hydroxy-6-methyl-2-aminotetralin
  作者：Joseph G. Cannon、Dale L. Koble、John Paul Long、Turkiz Verimer

  DOI：10.1021/jm00181a010

  日期：1980.7

  The title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation. A sequence leading to a key synthetic intermediate, 5-methoxy-6-methyl-2-tetralone, has been developed. In animal test models for dopamine-like effects, the title compounds demonstrated qualitative and quantitative differences from the isomeric 5-methyl-6-hydroxy-2-aminotetralins and from 5,6-dihydroxy-2-aminotetralins. Two of the compounds were potent in a cat cardioaccelerator nerve assay, which involves dopamine receptors.