3-benzyloxy-4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylic acid ethyl ester | 1012037-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-benzyloxy-4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylic acid ethyl ester
• 英文别名: ethyl 3-(benzyloxy)-4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylate；Ethyl 4-hydroxy-5,6,8-trimethoxy-3-phenylmethoxynaphthalene-2-carboxylate
• CAS: 1012037-71-6
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: KHKRHAUDYCPNLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylic acid ethyl ester 在 咪唑 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 ammonium acetate 、 水 、 氢气 、 硼酸 、 potassium carbonate 、 戴斯-马丁氧化剂 、 异氰酸苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 198.35h， 生成 methyl 4-[tert-butyl(diphenyl)silyl]oxy-5',7',8',9'-tetramethoxy-9-oxo-10-propylsulfanylspiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
  参考文献：
  名称：

  Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation

  摘要：

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

  DOI：

  10.1021/jo200399z
• 作为产物：
  描述：

  ethyl 3,4-dihydro-5,6,8-trimethoxy-3,4-dioxonaphthalene-2-carboxylate 在 sodium dithionite 、 水 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 120.08h， 生成 3-benzyloxy-4-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylic acid ethyl ester 、 4-benzyloxy-3-hydroxy-5,6,8-trimethoxynaphthalene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation

  摘要：

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

  DOI：

  10.1021/jo200399z

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。
• Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation
  作者：Andrew N. Lowell、Michael W. Fennie、Marisa C. Kozlowski

  DOI：10.1021/jo200399z

  日期：2011.8.19

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.