4-hydroxy-1,5-dimethoxy-2-methyl-naphthalene | 22273-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-1,5-dimethoxy-2-methyl-naphthalene
• 英文别名: 4-hydroxy-1,5-dimethoxy-2-methylnaphthalene；2-Methyl-4-hydroxy-1,5-dimetoxynaphthalin；4,8-Dimethoxy-3-methyl-naphthol-(1)；4,8-Dimethoxy-3-methylnaphthalen-1-ol
• CAS: 22273-59-2
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: FJUIVSGSOQEMSM-UHFFFAOYSA-N

物化性质

• 沸点：
  395.0±37.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1,5-dimethoxy-2-methyl-naphthalene 在 硝酸 、 四氯化锡 、 magnesium bromide 作用下， 以 硝基甲烷 为溶剂， 反应 12.0h， 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：

  兰雪醌 在 盐酸 、 氢氧化钾 、 tin(ll) chloride 、 silver(l) oxide 作用下， 反应 2.0h， 生成 4-hydroxy-1,5-dimethoxy-2-methyl-naphthalene
  参考文献：
  名称：

  Total Synthesis of (.+-.)-Plumbazeylanone.

  摘要：

  利用具有萘醌单元和萘酚单元的非对称亚甲基桥接二聚体 11b 作为关键中间体，通过 11 个步骤成功地首次全合成了萘醌三聚体 plumbazeylanone (1)。该合成具有亲核 1、2-加成反应和二酮-苯酚型重排的区域选择性。

  DOI：

  10.1248/cpb.46.1660

文献信息

• 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。
• 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。
• Total Synthesis of (.+-.)-Plumbazeylanone, A Naphthoquinone Trimer from Plumbago zeylanica.
  作者：Tetsuya TAKEYA、Manabu KAJIYAMA、Chikara NAKAMURA、Seisho TOBINAGA

  DOI：10.1248/cpb.47.209

  日期：——

  We have investigated the total synthesis of (±)-plumbazeylanone (1), a naphthoquinone trimer based on two different pathways (I) and (II). The synthetic approach based on pathway (I) was not successful. However, the first synthesis of 1 from plumbagin (2a) was achieved by utilizing an unsymmetrical methylene-bridged dimer (20b), with a naphthoquinone unit and a naphthalene unit as a key intermediate, based on pathway (II), in 11 steps with an overall yield of 5.9%. This synthesis features regioselective nucleophilic 1, 2-addition of the naphthyllithium reagent 4a to the C-1 position of naphthoquinone 20b, and the regio- and stereoselective dienone-phenol-type rearrangement of the 1, 2-adduct 21b (1, 2-migration of the naphthyl group to the C3-position on 21b) with 2 N-NaOH.

  我们研究了 (±)-plumbazeylanone (1) 的全合成，这是一种基于两种不同途径 (I) 和 (II) 的萘醌三聚体。基于途径(I)的合成方法并不成功。然而，首次从白花丹素 (2a) 合成 1 是通过利用不对称亚甲基桥联二聚体 (20b)，以萘醌单元和萘单元作为关键中间体，基于途径 (II)，经过 11 个步骤实现的总收益率为5.9%。该合成的特点是萘基锂试剂 4a 与萘醌 20b 的 C-1 位进行区域选择性亲核 1, 2-加成，以及 1, 2-加合物 21b (1, 2-用 2 N-NaOH 将萘基迁移至 21b) 上的 C3 位。
• Total Synthesis of (.+-.)-Plumbazeylanone.
  作者：Tetsuya TAKEYA、Manabu KAJIYAMA、Chikara NAKAMURA、Seisho TOBINAGA

  DOI：10.1248/cpb.46.1660

  日期：——

  The first total synthesis of plumbazeylanone (1), which is a trimer of naphthoquinone, was carried out successfully utilizing the unsymmetrical methylene-bridged dimer with the naphthoquinone unit and the naphthol unit, 11b as a key intermediate in 11 steps. This synthesis features a regioselective nucleophilic 1, 2-addition reaction and dinone-phenol-type rearrangement.

  利用具有萘醌单元和萘酚单元的非对称亚甲基桥接二聚体 11b 作为关键中间体，通过 11 个步骤成功地首次全合成了萘醌三聚体 plumbazeylanone (1)。该合成具有亲核 1、2-加成反应和二酮-苯酚型重排的区域选择性。