1,2,4,5,8-pentamethoxynaphthalene | 122182-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,4,5,8-pentamethoxynaphthalene
• CAS: 122182-21-2
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: KHQTXXDFBAQVNL-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C(Solv: hexane (110-54-3))
• 沸点：
  424.8±40.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,4,5,8-pentamethoxynaphthalene 在 silver(II) oxide 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 生成 6-acetyl-2,5,8-trimethoxy-1,4-naphthoquinine
  参考文献：
  名称：

  Koning, Charles B.; Giles, Robin G.F.; Engelhardt, Lutz M., Journal of the Chemical Society. Perkin transactions I, 1988, p. 3209 - 3216

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4,5,8-tetramethoxynaphthalene 在 lead(IV) acetate 、 sodium hydroxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.0h， 生成 1,2,4,5,8-pentamethoxynaphthalene
  参考文献：
  名称：

  Monosubstituted Tetramethoxynaphthalenes

  摘要：

  作为合成单取代萘扎林和蒽环类化合物的新中间体，几种具有 CH3、COOH、CN、Br、OAc、OH 和 OMe 等取代基的四甲氧基萘被从 1,4,5,8-四甲氧基萘和 2-甲酰基-1,4,5,8-四甲氧基萘合成出来。

  DOI：

  10.1246/bcsj.62.1211

文献信息

• A Concise Synthesis of the Naphthalene Portion of Purpuromycin
  作者：Andrew N. Lowell、Michael W. Fennie、Marisa C. Kozlowski

  DOI：10.1021/jo7024114

  日期：2008.3.1

  A concise synthesis of naphthalene compounds for incorporation into a synthetic sequence for the rubromycin family of natural products is presented. These highly substituted naphthalenes are generated in seven and nine steps, respectively, from 2,4,5-trimethoxybenzaldehyde. Three ring-forming methods were explored and the controlled oxygenation of different positions was investigated to yield differentially

  提出了一种萘化合物的简明合成方法，该方法可掺入天然产物红霉素家族的合成序列中。这些高度取代的萘分别由2,4,5-三甲氧基苯甲醛分七个步骤和九个步骤生成。探索了三种成环方法，并研究了不同位置的受控氧合以产生差异取代/受保护的系统。最终产品的关键步骤包括Stobbe缩合反应形成环系统，以及一系列新的区域选择性氧化反应，以引入所需的氧官能度。这些萘产物包含正交保护基，适合与各种偶联剂结合使用。
• Convenient Synthesis of 1,4-Naphthoquinones from Polymethoxynaphthalenes. Oxidative Demethylation with Silver-Catalyzed Ammonium Peroxodisulfate
  作者：Yasuhiro Tanoue、Kazunori Sakata、Mamoru Hashimoto、Shin-ichi Morishita、Moritsugu Hamada、Norihisa Kai、Takeshi Nagai

  DOI：10.1246/bcsj.67.2593

  日期：1994.9

  The oxidative demethylation of polymethoxynaphthalenes such as 1,4-di, 1,4,5-tri, 1,4,5,8-tetra, and 1,2,4,5,8-pentamethoxynaphthalenes with silver-catalyzed ammonium peroxodisulfate gave the corresponding 1,4-naphthoquinones in good yield under mild reaction conditions.

  在银催化的过二硫酸铵作用下，1,4-二、1,4,5-三、1,4,5,8-四和 1,2,4,5,8-五甲氧基萘等多甲氧基萘在温和的反应条件下发生氧化脱甲基反应，得到了相应的 1,4-萘醌，收率很高。
• Alternative Spiroketalization Methods toward Purpuromycin: A Hemiketal Conjugate Addition Strategy and Use of an Electron-Rich Isocoumarin Precursor
  作者：Rakeshwar Bandichhor、Andrew N. Lowell、Marisa C. Kozlowski

  DOI：10.1021/jo200398v

  日期：2011.8.19

  Two methods are presented that were designed to circumvent the persistent problem of benzofuran formation and instead yield a spiroketal of the rubromycin family type. First, using an alternative disconnection, a hemiketal conjugate addition to a naphthaquinone electrophile was investigated. Synthesis of the requisite electrophile provided insight into the selective oxidation and functionalization of the naphthalene portion. Second, the electronic features of the isocoumarin ring system were adjusted, and the corresponding reactivity further supports the hypothesis that electron-rich isocoumarins are capable of spiroketalization. Robust, flexible syntheses from simple precursors were developed that allowed multiple reduced isocoumarins to be generated. Combined, the data presented herein give insight into the sensitivities of this family and illuminate other potential methods of spiroketalization. In addition, the convergent assembly of substrates containing different naphthaquinone and isocoumarin subunits highlights the utility of our 1,3-dipolar cycloaddition approach to generate analogs of these structures for SAR, as well as chemical reactivity studies.
• Clive, Derrick L. J.; Middleton, Donald S., Israel Journal of Chemistry, 1991, vol. 31, # 3, p. 211 - 214
  作者：Clive, Derrick L. J.、Middleton, Donald S.

  DOI：——

  日期：——
• DE KONING, CHARLES B.; GILES, ROBIN G. F., ENGELHARDT, LUTZ M.; WHITE, AL+, J. CHEM. SOC. PERKIN TRANS. PT1., N12, 1988, 3209-3216
  作者：DE KONING, CHARLES B.、 GILES, ROBIN G. F., ENGELHARDT, LUTZ M.、 WHITE, AL+

  DOI：——

  日期：——