6,8-Dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid | 207862-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,8-Dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid
• 英文别名: 6,8-Dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid；6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
• CAS: 207862-88-2
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ATIBMIAIZFMEQW-UHFFFAOYSA-N

物化性质

• 沸点：
  441.6±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-Dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid 在 rhodium(II) acetate dimer 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 29.08h， 生成 1,3-Dimethoxy-5,6,8,9-tetrahydro-5,8-methano-benzocyclohepten-7-one
  参考文献：
  名称：

  Norcaradienes from the Intramolecular Cyclopropanation Reactions of Diazomethyl Ketones. Valuable Intermediates for the Synthesis of Polycyclic Diterpenes

  摘要：

  DOI：

  10.1055/s-1998-5932
• 作为产物：
  描述：

  3-(3,5-二甲氧基苯基)-1-丙醇 在 四溴化碳 、 sodium hydride 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 101.25h， 生成 6,8-Dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid
  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

文献信息

• Synthetic studies on Rabdosia diterpene lactones I: The preparation of a key tricyclic intermediate
  作者：Martin J. Kenny、Lewis N. Mander、S.Paul Sethi

  DOI：10.1016/s0040-4039(00)83918-0

  日期：1986.1

  A strategy is proposed for the synthesis of Rabdosia diterpene lactones, . effusin 2 and the preparation of a suitable tricyclic intermediate 6 described.

  提出了用于合成立陶宛二萜内酯的策略。所述的游动蛋白2和合适的三环中间体6的制备描述了。
• First Synthesis of Dopamine and Rotigotin Analogue 2-Amino-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalene
  作者：Süleyman Yılmaz、Süleyman Göksu

  DOI：10.1080/00397911.2013.841939

  日期：2014.4.18

  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.]
• Norcaradienes from the Intramolecular Cyclopropanation Reactions of Diazomethyl Ketones. Valuable Intermediates for the Synthesis of Polycyclic Diterpenes
  作者：Jonathan C. Morris

  DOI：10.1055/s-1998-5932

  日期：1998.3