5,6,7,8-tetrahydro-2-methoxynaphthalene-1,4-dione | 91143-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 5,6,7,8-tetrahydro-2-methoxynaphthalene-1,4-dione
• 英文别名: 2-methoxy-5,6,7,8-tetrahydro-1,4-naphthoquinone；2-methoxy-5,6,7,8-tetrahydronaphthalene-1,4-dione；5,6,7,8-Tetrahydro-2-methoxy-naphthochinon-(1.4)；6-Methoxy-1,2,3,4-tetrahydro-naphthochinon-(5,8)
• CAS: 91143-21-4
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: CXEKGVJHOFWPCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-2-methoxynaphthalene-1,4-dione 在 sodium azide 、 硫酸 作用下， 反应 16.0h， 以19%的产率得到3-methoxy-6,7,8,9-tetrahydro-1H-benzazepine-2,5-dione
  参考文献：
  名称：

  外消旋6,7,8,9-四氢-3-羟基-1H-1-苯并ze庚因-2,5-二酮作为N-甲基-d-天冬氨酸（NMDA）和α-氨基-3-羟基-拮抗剂的合成5-甲基异恶唑-4-丙酸（AMPA）受体。

  摘要：

  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

  DOI：

  10.1021/jm960724e
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 1,2-双(叔丁基氨基)乙烷 、 氧气 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 20.0~23.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 5,6,7,8-tetrahydro-2-methoxynaphthalene-1,4-dione
  参考文献：
  名称：

  A divergent and selective synthesis of ortho- and para-quinones from phenols

  摘要：

  We describe a divergent synthesis of substituted ortho- and para-quinones by catalytic aerobic oxygenation of phenols. Substituted quinones are omnipresent in chemistry and biology, but their synthesis frequently suffers from low efficiency and poor scope. Our methodology employs a catalytic aerobic di-functionalization of phenols to aryloxy-ortho-quinones. Regioselective substitution with an alcohol provides the alkoxy substituted ortho- or para-quinone, while hydrolysis affords the para-hydroxyquinone. These are mild and selective conditions for the synthesis of diversely substituted quinones from readily available phenol starting materials. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.095

文献信息

• Hydroxyquinone annelation
  作者：Marcus A. Tius、Jean M. Cullingham、S. Ali

  DOI：10.1039/c39890000867

  日期：——

  The epoxidation reaction of alkoxyallene (4a) produced epoxy ketoaldehyde (5a) through an intermediate oxyallyl zwitterion; an intramolecular aldol reaction, followed by air oxidation produced hydroxyquinone (6).

  烷氧基丙二烯（4a）的环氧化反应通过中间的羟基烯丙基两性离子产生环氧酮醛（5a）。分子内的羟醛反应，然后进行空气氧化，生成羟基醌（6）。
• 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.

  本发明涉及通过多步合成，包括Diels-Alder反应制备氮杂环庚烷的方法。还涉及治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丧失的方法，以及治疗包括阿尔茨海默病、肌萎缩性侧索硬化症、亨廷顿病和唐氏综合症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、惊厥、诱导麻醉和治疗或预防阿片类药物耐受性，通过向需要这种治疗的动物注射具有高亲和力的NMDA甘氨酸位点结合能力的氮杂环庚烷来实现。
• 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。
• Tori, Motoo; Sono, Masakazu; Takikawa, Keiko, Journal of Chemical Research, Miniprint, 1999, # 8, p. 2001 - 2019
  作者：Tori, Motoo、Sono, Masakazu、Takikawa, Keiko、Matsuda, Reiko、Toyota, Masao、Cheminat, Annie、Asakawa, Yoshinori

  DOI：——

  日期：——
• Hecker,E.; Lattrell,R., Justus Liebigs Annalen der Chemie, 1963, vol. 662, p. 48 - 66
  作者：Hecker,E.、Lattrell,R.

  DOI：——

  日期：——