4,4',8,8'-tetramethoxy-3,3'-dimethyl[2,2']-di-1,1'-naphthol | 344799-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,4',8,8'-tetramethoxy-3,3'-dimethyl[2,2']-di-1,1'-naphthol
• 英文别名: 2-(1-Hydroxy-4,8-dimethoxy-3-methylnaphthalen-2-yl)-4,8-dimethoxy-3-methylnaphthalen-1-ol
• CAS: 344799-90-2
• 化学式: C₂₆H₂₆O₆
• 分子量: 434.489
• InChiKey: ZGWLOCJUMSEJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4',8,8'-tetramethoxy-3,3'-dimethyl[2,2']-di-1,1'-naphthol 在 硝酸 、 magnesium bromide 作用下， 反应 6.0h， 生成 3,3’-双矶松素
  参考文献：
  名称：

  The aryl–aryl coupling reaction of 1-naphthol with SnCl 4 for 2,2′-binaphthol synthesis and its application to the biomimetic synthesis of binaphthoquinone isolated from Plumbago zeylanica

  摘要：

  A simple method for the direct synthesis of 2,2 ' -binaphthols was developed, utilizing aryl-aryl coupling reaction via electron donor-acceptor complexes of l-naphthols with SnCl4. Heating of the complex in a sealed tube afforded the corresponding o-o coupling product in excellent yield. This method was utilized for a biomimetic synthesis of the binaphthoquinone, 3,3 ' -biplumbagin, isolated from Plumbago zeylanica. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00337-9
• 作为产物：
  描述：

  4-hydroxy-1,5-dimethoxy-2-methyl-naphthalene 在 氧气 、 四氯化锡 作用下， 以 硝基甲烷 为溶剂， 反应 7.0h， 以52%的产率得到4,4',8,8'-tetramethoxy-3,3'-dimethyl[2,2']-di-1,1'-naphthol
  参考文献：
  名称：

  SnCl 4介导的联萘醌和二萘呋喃骨架的氧化反应及其在天然产物合成中的应用

  摘要：

  通过1-萘酚的电子供体-受体配合物的氧化反应，通过氧化反应，直接合成2,2'-联萘醌和二萘并[1,2- b ; 2'，1'- d ]呋喃的简单方法。在不存在或存在双氧的情况下的SnCl 4。作为该方法在天然产物合成中的应用，我们描述了几种双萘甲醌，3,3'-双juglone，3,3'-biplumbagin和艾力汀的简便仿生合成方法。

  DOI：

  10.1016/s0040-4039(03)00213-2

文献信息

• Aerobic oxidative dimerization of 1-naphthols to 2,2′-binaphthoquinones mediated by SnCl4 and its application to natural product synthesis
  作者：Tetsuya Takeya、Hirohisa Doi、Tokutaro Ogata、Iwao Okamoto、Eiichi Kotani

  DOI：10.1016/j.tet.2004.07.073

  日期：2004.10

  developed a simple method for the direct synthesis of 2,2′-binaphthoquinones, utilizing oxidative dimerization via electron donor–acceptor complex formation of 1-naphthols with SnCl4 in the presence of dioxygen. This oxidation involves a catalytic cycle of SnCl4, and the reaction mechanism is discussed. As an application of this method to natural products synthesis, we describe facile biomimetic syntheses

  我们开发了一种简单的直接合成2,2'-双萘醌的方法，该方法通过在存在双氧的条件下通过电子供体-受体与1-nphthols的SnCl 4的电子供体-受体复合物形成氧化二聚作用来进行。该氧化涉及SnCl 4的催化循环，并讨论了反应机理。作为该方法在天然产物合成中的一种应用，我们描述了联萘醌3,3'-双juglone，3,3'-双酚苄青霉素和艾替丁酮的简便仿生合成方法。
• SnCl4-mediated oxidative reaction for formation of binaphthoquinone and dinaphthofuran frameworks and its application to natural product synthesis
  作者：Tokutaro Ogata、Iwao Okamoto、Hirohisa Doi、Eiichi Kotani、Tetsuya Takeya

  DOI：10.1016/s0040-4039(03)00213-2

  日期：2003.3

  A simple method was developed for the direct synthesis of 2,2′-binaphthoquinones and dinaphtho[1,2-b;2′,1′-d]furans, utilizing an oxidative reaction via electron donor–acceptor complexes of 1-naphthols with SnCl4 in the absence or presence of dioxygen. As an application of this method to natural product synthesis, we describe a facile biomimetic synthesis of several binaphthoquinones, 3,3′-bijuglone

  通过1-萘酚的电子供体-受体配合物的氧化反应，通过氧化反应，直接合成2,2'-联萘醌和二萘并[1,2- b ; 2'，1'- d ]呋喃的简单方法。在不存在或存在双氧的情况下的SnCl 4。作为该方法在天然产物合成中的应用，我们描述了几种双萘甲醌，3,3'-双juglone，3,3'-biplumbagin和艾力汀的简便仿生合成方法。
• SnCl 4 -mediated oxidative biaryl coupling reaction of 1-naphthol and subsequent ring closure of 2,2′-binaphthol to the dinaphthofuran framework
  作者：Tetsuya Takeya、Hirohisa Doi、Tokutaro Ogata、Tsuyoshi Otsuka、Iwao Okamoto、Eiichi Kotani

  DOI：10.1016/j.tet.2004.05.077

  日期：2004.7

  A simple method for the direct synthesis of 2,2′-binaphthols 2 and dinaphtho[1,2-b;2′,1′-d]furans 3 under mild conditions was developed, utilizing a biaryl coupling reaction via electron donor–acceptor complexes of 1-naphthols with SnCl4. Heating of the complex in a sealed tube for (18–24 h) afforded the corresponding o–o coupled product 2 in excellent yield. Prolonged reaction (56–65 h) under the

  利用电子供体-受体的联芳基偶联反应，开发了一种在温和条件下直接合成2,2'-联萘酚2和二萘并[1,2- b ; 2'，1'- d ]呋喃3的简单方法1-萘酚与SnCl 4的配合物。该复合物在密封管中加热（18-24小时），得到相应的ö - ö偶联产物2的优良率。在相同条件下长时间反应（56–65小时）一步即可获得3的高收率。我们还发现，对于在C-1位上没有羟基以外的取代基的α-萘酚，区域选择性o –o进行了偶联反应。产物2a，2b和2g应该用作天然存在的3，3′-双juglone，3，3′-biplumbagin和艾力汀的合成中间体。
• The aryl–aryl coupling reaction of 1-naphthol with SnCl 4 for 2,2′-binaphthol synthesis and its application to the biomimetic synthesis of binaphthoquinone isolated from Plumbago zeylanica
  作者：Iwao Okamoto、Hirohisa Doi、Eiichi Kotani、Tetsuya Takeya

  DOI：10.1016/s0040-4039(01)00337-9

  日期：2001.4

  A simple method for the direct synthesis of 2,2 ' -binaphthols was developed, utilizing aryl-aryl coupling reaction via electron donor-acceptor complexes of l-naphthols with SnCl4. Heating of the complex in a sealed tube afforded the corresponding o-o coupling product in excellent yield. This method was utilized for a biomimetic synthesis of the binaphthoquinone, 3,3 ' -biplumbagin, isolated from Plumbago zeylanica. (C) 2001 Elsevier Science Ltd. All rights reserved.