3,4-bis(benzyloxy)-5,6,8-trimethoxynaphthalene-2-carbaldehyde | 1315508-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-bis(benzyloxy)-5,6,8-trimethoxynaphthalene-2-carbaldehyde
• 英文别名: 5,6,8-Trimethoxy-3,4-bis(phenylmethoxy)naphthalene-2-carbaldehyde
• CAS: 1315508-00-9
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: KXKJWUNKJBLRBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-bis(benzyloxy)-5,6,8-trimethoxynaphthalene-2-carbaldehyde 在 咪唑 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 ammonium acetate 、 氢气 、 硼酸 、 异氰酸苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 46.08h， 生成 7,8-dibenzyloxy-6-[1-(tert-butyldimethylsilanyloxy)-4-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-3,4-dioxobutyl]-1-oxo-1H-isochromene-3-carboxylic acid methyl 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
• 作为产物：
  描述：

  ethyl 3,4-dihydro-5,6,8-trimethoxy-3,4-dioxonaphthalene-2-carboxylate 在 lithium aluminium tetrahydride 、 sodium dithionite 、 水 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 9.08h， 生成 3,4-bis(benzyloxy)-5,6,8-trimethoxynaphthalene-2-carbaldehyde
  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

• 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.