1,2-二氢-6-甲氧基-7-甲基萘 | 122334-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,2-二氢-6-甲氧基-7-甲基萘
• 英文名称: 1,2-dihydro-6-methoxy-7-methylnaphthalene
• 英文别名: 3,4-dihydro-6-methyl-7-methoxynaphthalene；6-methoxy-7-methyl-1,2-dihydronaphthalene
• CAS: 122334-03-6
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: AFFLHOXUXNCXJD-UHFFFAOYSA-N

物化性质

• 熔点：
  49.6-50.4 °C
• 沸点：
  267.9±29.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-二氢-6-甲氧基-7-甲基萘 在 铂 盐酸 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 76.17h， 生成 2-(di-n-propylamino)-6-methyl-7-methoxytetralin
  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-(4-methoxy-3-methylphenyl)butyric acid 在 sodium tetrahydroborate 、 potassium hydrogensulfate 、 甲烷磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 1,2-二氢-6-甲氧基-7-甲基萘
  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

文献信息

• Model Studies Toward the Synthesisof Natural Indans Utilizing a Thallium(III)-Mediated Ring-ContractionReaction
  作者：Helena M. Ferraz、Andrea M. Aguilar、Luiz F. Silva

  DOI：10.1055/s-2003-39172

  日期：——

  6-Methoxy-1-tetralone was transformed in six steps into an indan derivative related to the sesquiterpenes mutisianthol and jungianol. Key steps involve a thallium(III)-promoted ring-contraction (to assemble the indan unit) and a Wittig olefination (to attach the side chain).

  6-甲氧基-1-四氢萘酮经过六个步骤转化为与倍半萜化合物mutisianthol和jungianol相关的茨菇烷衍生物。关键步骤包括一个铊(III)催化的环收缩反应（用以组装茨菇烷单元）和一个Wittig烯化反应（用以连接侧链）。
• Photochemistry of stilbenes. 8. Eliminative photocyclization of o-methoxystilbenes
  作者：Frank B. Mallory、M. Jonathan Rudolph、Soon M. Oh

  DOI：10.1021/jo00280a032

  日期：1989.9
• MALLORY, FRANK B.;RUDOLPH, M. JONATHAN;OH, SOON M., J. ORG. CHEM., 54,(1989) N9, C. 4619-4626
  作者：MALLORY, FRANK B.、RUDOLPH, M. JONATHAN、OH, SOON M.

  DOI：——

  日期：——