5,8-Dihydro-2,6,7-trimethyl-1,4-naphthochinon | 55699-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,8-Dihydro-2,6,7-trimethyl-1,4-naphthochinon
• 英文别名: 2,6,7-trimethyl-5,8-dihydro-[1,4]naphthoquinone；2,6,7-Trimethyl-5,8-dihydro-[1,4]naphthochinon；5,8-dihydro-2,6,7-trimethyl-1,4-naphthoquinone；2,6,7-trimethyl-5,8-dihydronaphthalene-1,4-dione
• CAS: 55699-87-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: ORYWMRBJWPFTKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,8-Dihydro-2,6,7-trimethyl-1,4-naphthochinon 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以796.9 mg的产率得到2,6,7-trimethyl-1,4-naphthoquinone
  参考文献：
  名称：

  获取多取代 2-甲基-1,4-萘醌衍生物的区域选择性方法平台：范围和限制

  摘要：

  已经建立了一个合成方法平台，以访问在萘醌核心的芳环上官能化的多取代 3-苄基甲二酮衍生物的重点库。探索了两条主要路线：1）萘酚路线，从 α-四氢萘酮或苯丙酮开始，以及 2）区域选择性 Diels-Alder 反应，从各种二烯和两个 2-溴-5（或 6）-甲基-1,4-苯醌。通过使用黄药介导的自由基加成/环化序列来构建 6-取代的甲萘醌亚基，合成了 6-取代的 2-甲基萘酚。此外，还通过萘酚路线开发了一种有效且简单的新途径，允许从常见的商业支架形成 6 或 7 取代的 3-（取代苄基）甲萘醌区域异构体，有利于阶梯经济。我们以 34 种化合物为例的合成方法允许推导结构-活性关系，用作开发新的抗疟氧化还原活性多取代苄基甲萘二酮衍生物的基础。

  DOI：

  10.1002/ejoc.201600144
• 作为产物：
  描述：

  甲基苯醌 在 乙醇 、 氢溴酸 、 三氯化铁 、 溶剂黄146 作用下， 生成 5,8-Dihydro-2,6,7-trimethyl-1,4-naphthochinon
  参考文献：
  名称：

  SYNTHESES AND REACTIONS OF SUBSTITUTED α-NAPHTHOQUINONES

  摘要：

  DOI：

  10.1021/jo01219a005

文献信息

• [EN] TOTAL SYNTHESIS OF REDOX-ACTIVE 1.4-NAPHTHOQUINONES AND THEIR METABOLITES AND THEIR THERAPEUTIC USE AS ANTIMALARIAL AND SCHISTOMICIDAL AGENTS<br/>[FR] SYNTHÈSE TOTALE DE 1,4-NAPHTOQUINONES PRÉSENTANT UNE ACTIVITÉ D'OXYDO-RÉDUCTION ET DE LEURS MÉTABOLITES ET LEUR UTILISATION THÉRAPEUTIQUE COMME AGENTS ANTIPALUDIQUES ET SCHISTOMICIDES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2012131010A1

  公开（公告）日：2012-10-04

  Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and their use as antimalarial or antischistosomal agents.

  萘醌、氮杂萘醌和苯基蒽醌，它们的合成过程以及它们作为抗疟疾或抗血吸虫药物的用途。
• Preparation process of naphthoquinone derivative and intermediate for
  申请人：Eisai Chemical Co., Ltd.

  公开号：US05412124A1

  公开（公告）日：1995-05-02

  Disclosed herein are a naphthoquinone derivative represented by the following formula: ##STR1## wherein R.sup.1 means a hydrogen atom or methyl group, R.sup.2 is a hydrogen atom or methyl group, n stands for 0 or an integer of 1-9, and a linkage is a single bond or double bond with the proviso that if n is an integer of 2-9, the linkages may be identical with or different optionally from each other, such as a vitamin K derivative; and a process for producing the naphthoquinone derivative at a high yield without forming any geometric isomer; as well as 1,4,4.sub.a,5,8,9.sub.a -hexahydro-4.sub.a .alpha.-alkenyl-1.alpha.,4.alpha.-methanoanthraquinone derivatives and 1,4,4.sub.a,5,8,9.sub.a -hexahydro-1.alpha.,4.alpha.-methanoanthraquinone derivatives which are useful as intermediates for the preparation of the naphthoquinone derivatives.

  本文披露了一种萘醌衍生物，其化学式如下：##STR1## 其中，R.sup.1表示氢原子或甲基基团，R.sup.2表示氢原子或甲基基团，n代表0或1-9的整数，连接是单键或双键，但如果n为2-9的整数，则连接可以是相同的或不同的，例如维生素K衍生物；以及一种高产率制备萘醌衍生物并且不形成任何几何异构体的方法；以及有用于制备萘醌衍生物的中间体1,4,4.sub.a,5,8,9.sub.a-六氢-4.sub.a .alpha.-烯基-1.alpha.,4.alpha.-甲基-蒽醌衍生物和1,4,4.sub.a,5,8,9.sub.a-六氢-1.alpha.,4.alpha.-甲基-蒽醌衍生物。
• 1,4,4.sub.a 5,8,9.sub.a
  申请人：Eisai Chemical Co., Ltd.

  公开号：US05608092A1

  公开（公告）日：1997-03-04

  The present invention relates to intermediates useful for the preparation of vitamin K derivatives.

  本发明涉及用于制备维生素K衍生物的中间体。
• TOTAL SYNTHESIS OF REDOX-ACTIVE 1.4-NAPHTHOQUINONES AND THEIR METABOLITES AND THEIR THERAPEUTIC USE AS ANTIMALARIAL AND SCHISTOMICIDAL AGENTS
  申请人：Davioud-Charvet Elisabeth

  公开号：US20140121238A1

  公开（公告）日：2014-05-01

  Naphthoquinones, azanaphthoquinones and benxanthones, their process of synthesis and methods of their use as antimalarial or antischistosomal agents.

  萘醌，氮杂萘醌和苯并蒽醌，它们的合成过程及其作为抗疟疾或抗血吸虫药物的使用方法。
• Tuning Lewis Acidity of Metal–Organic Frameworks via Perfluorination of Bridging Ligands: Spectroscopic, Theoretical, and Catalytic Studies
  作者：Pengfei Ji、Tasha Drake、Akiko Murakami、Pau Oliveres、Jonathan H. Skone、Wenbin Lin

  DOI：10.1021/jacs.8b05765

  日期：2018.8.22

  The Lewis acidity of metal-organic frameworks (MOFs) has attracted much research interest in recent years. We report here the development of two quantitative methods for determining the Lewis acidity of MOFs-based on electron paramagnetic resonance (EPR) spectroscopy of MOF-bound superoxide (O-2(center dot-)) and fluorescence spectroscopy of MOF-bound N-methylacridone (NMA)-and a simple strategy that significantly enhances MOF Lewis acidity through ligand perfluorination. Two new perfluorinated MOFs, Zr-6-fBDC and Zr-6-fBPDC, where H(2)fBDC is 2,3,5,6-tetrafluoro-1,4-benzenedicarboxylic acid and H(2)fBPD C is 2,2',3,3',5,5',6,6'-octafluoro-4,4'-biphenyldicarboxylic acid, were shown to be significantly more Lewis acidic than nonsubstituted UiO-66 and UiO-67 as well as the nitrated MOFs Zr-6-BDC-NO2 and Zr-6-BPDC-(NO2)(2). Zr-6-fBDC was shown to be a highly active single-site solid Lewis acid catalyst for Diels- Alder and arene C-H iodination reactions. Thus, this work establishes the important role of ligand perfluorination in enhancing MOF Lewis acidity and the potential of designing highly Lewis acidic MOFs for fine chemical synthesis.