1,4-dihydroxy-2-methoxy-6,7-dimethyl-5,8-dihydronaphthalene | 96040-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-dihydroxy-2-methoxy-6,7-dimethyl-5,8-dihydronaphthalene
• 英文别名: 5,8-dihydro-2-methoxy-6,7-dimethylnaphthalene-1,4-diol；2-methoxy-6,7-dimethyl-5,8-dihydro-naphthalene-1,4-diol；2-Methoxy-6,7-dimethyl-5,8-dihydro-naphthalin-1,4-diol；5,8-dihydro-6,7-dimethyl-2-methoxynaphthalene-1,4-diol；5,8-Dihydro-2-methoxy-6,7-dimethyl-1,4-naphthohydrochinon；2-methoxy-6,7-dimethyl-5,8-dihydronaphthalene-1,4-diol
• CAS: 96040-69-6
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: RYNCZCOVALXFPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dihydroxy-2-methoxy-6,7-dimethyl-5,8-dihydronaphthalene 在 甲醇 、 三氯化铁 作用下， 生成 2-methoxy-6,7-dimethyl-5,8-dihydro-[1,4]naphthoquinone
  参考文献：
  名称：

  Trave et al., Chimica e l'Industria (Milan, Italy), 1959, vol. 41, p. 19,25

  摘要：

  DOI：
• 作为产物：
  描述：

  甲氧苯醌 在 氢溴酸 、 溶剂黄146 作用下， 生成 1,4-dihydroxy-2-methoxy-6,7-dimethyl-5,8-dihydronaphthalene
  参考文献：
  名称：

  Trave et al., Chimica e l'Industria (Milan, Italy), 1959, vol. 41, p. 19,25

  摘要：

  DOI：

文献信息

• Azepine synthesis via a diels-alder reaction
  申请人：State of Oregon, acting by and through The Oregon State Board of Higher

  公开号：US05476933A1

  公开（公告）日：1995-12-19

  Disclosed are methods of preparing azepines by a multistep synthesis including a Diels-Alder reaction. Also disclosed are methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating or preventing opiate tolerance are disclosed by administering to an animal in need of such treatment an azepine which has high binding to the NMDA glycine site.

  揭示了通过多步合成包括 Diels-Alder 反应制备环庚烯的方法。还揭示了治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丢失的方法，以及治疗包括阿尔茨海默病、肌萎缩侧索硬化症、亨廷顿病和唐氏综合征在内的神经退行性疾病，治疗或预防兴奋性氨基酸过度活跃的不良后果，以及治疗焦虑、慢性疼痛、抽搐、诱导麻醉和治疗或预防阿片耐受性的方法，通过向需要此类治疗的动物施用对 NMDA 甘氨酸位点具有高结合能力的环庚烯来实现。
• Synthesis of Racemic 6,7,8,9-Tetrahydro-3-hydroxy-1<i>H</i>-1-benzazepine-2,5-diones as Antagonists of <i>N</i>-Methyl-<scp>d</scp>-aspartate (NMDA) and α-Amino-3-hydroxy-5-methylisoxazole-4-propionic Acid (AMPA) Receptors
  作者：Anthony P. Guzikowski、Edward R. Whittemore、Richard M. Woodward、Eckard Weber、John F. W. Keana

  DOI：10.1021/jm960724e

  日期：1997.7.1

  oocytes expressing rat brain NMDA and AMPA receptors. THHBADs are antagonists of NMDA and AMPA receptors with functional potency being dependent upon the substitution pattern on the tetrahydrobenzene moiety. The 7,8-dichloro-6-methyl (18a) and 7,8-dichloro-6-ethyl (18b) analogs are the most potent THHBADs prepared and have apparent antagonist dissociation constants (Kb values) of 0.0041 and 0.0028 microM

  描述了几种外消旋的6,7,8,9-四氢-3-羟基-1H-1-苯并ze庚因-2,5-二酮（THHBADs）的合成和药理特性。通过与5,6,7,8-四氢-2-甲氧基萘-1,4-二酮（THMND）的施密特反应完成合成，然后进行去甲基化。通过与2-甲氧基苯醌（5）或2-溴-5-甲氧基苯醌（14）和取代的1,3-丁二烯的Diels-Alder反应制备THMND。THHBADs的药理学特征是在非洲爪蟾卵母细胞中表达大鼠脑NMDA和AMPA受体的电记录。THHBAD是NMDA和AMPA受体的拮抗剂，其功能效力取决于四氢苯部分上的取代方式。7,8-二氯-6-甲基（18a）和7
• Azepine compounds
  申请人：State of Oregon, Acting by and through The Oregon State Board of Higher

  公开号：US05708168A1

  公开（公告）日：1998-01-13

  Disclosed are methods of preparing azepines by a multistep synthesis including a Diels-Alder reaction. Also disclosed are methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating or preventing opiate tolerance are disclosed by administering to an animal in need of such treatment an azepine which has high binding to the NMDA glycine site.

  本发明涉及一种通过多步合成包括Diels-Alder反应制备氮杂环庚烯的方法。同时，本发明还涉及一种通过给予具有高结合NMDA甘氨酸位点的氮杂环庚烯来治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术有关的神经元丢失，以及治疗阿尔茨海默病、肌萎缩性侧索硬化、亨廷顿病和唐氏综合征等神经退行性疾病，治疗兴奋性氨基酸过度活跃的不良后果，以及治疗焦虑、慢性疼痛、惊厥、诱导麻醉和治疗或预防鸦片类药物耐受性的方法。
• A useful synthon approach to bicyclic enols: acid-catalyzed and base-catalyzed rearrangements of Diels-Alder adducts of 2-methoxy-5-methyl-1,4-benzoquinone
  作者：Kenji Hayakawa、Kaoru Ueyama、Ken Kanematsu

  DOI：10.1021/jo00211a034

  日期：1985.5
• HAYAKAWA, KENJI;UEYAMA, KAORU;KANEMATSU, KEN, J. ORG. CHEM., 1985, 50, N 11, 1963-1969
  作者：HAYAKAWA, KENJI、UEYAMA, KAORU、KANEMATSU, KEN

  DOI：——

  日期：——