methyl 6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 1586815-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 1586815-05-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ZFZQRRVWKFOEFT-UHFFFAOYSA-N

物化性质

• 沸点：
  379.1±42.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 叠氮磷酸二苯酯 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 、 苯 为溶剂， 反应 84.0h， 生成 2-amino-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene hydrogen chloride
  参考文献：
  名称：

  First Synthesis of Dopamine and Rotigotin Analogue 2-Amino-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene

  摘要：

  The title compound was synthesized starting from 3-(3,5-dimethoxyphenyl)acrylic acid in 11 steps with 30% total yield. The reaction sequence hydrogenation of acrylic acid, reduction of acid to alcohol derivative with LiAlH4, reaction of alcohol with CBr4/PPh3, substitution reaction of alkyl halide to nitrile derivative with NaCN, hydrolysis of nitrile with NaOH, cyclization reaction of acid with PPA to give 1-tetralone, alpha-carboxylation of tetralone with Me2CO3 in the presence of NaH, reduction of ketone group with Et3SiH, hydrolysis of ester, Curtius rearrangement of acid with diphenylphosphoryl azide followed by conversion to carbamate, and finally hydrogenolysis of carbamate afforded 2-amino-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene hydrogen chloride salt. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.841939
• 作为产物：
  描述：

  4-(3,5-二甲氧基苯基)丁腈 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 51.25h， 生成 methyl 6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  First Synthesis of Dopamine and Rotigotin Analogue 2-Amino-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene

  摘要：

  The title compound was synthesized starting from 3-(3,5-dimethoxyphenyl)acrylic acid in 11 steps with 30% total yield. The reaction sequence hydrogenation of acrylic acid, reduction of acid to alcohol derivative with LiAlH4, reaction of alcohol with CBr4/PPh3, substitution reaction of alkyl halide to nitrile derivative with NaCN, hydrolysis of nitrile with NaOH, cyclization reaction of acid with PPA to give 1-tetralone, alpha-carboxylation of tetralone with Me2CO3 in the presence of NaH, reduction of ketone group with Et3SiH, hydrolysis of ester, Curtius rearrangement of acid with diphenylphosphoryl azide followed by conversion to carbamate, and finally hydrogenolysis of carbamate afforded 2-amino-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene hydrogen chloride salt. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.841939