7,8-dibenzyloxy-6-[3-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester | 1315508-06-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 7,8-dibenzyloxy-6-[3-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 1-oxo-7,8-bis(phenylmethoxy)-6-[3-[[5,6,8-trimethoxy-3,4-bis(phenylmethoxy)naphthalen-2-yl]methyl]-4,5-dihydro-1,2-oxazol-5-yl]isochromene-3-carboxylate
• CAS: 1315508-06-5
• 化学式: C₅₆H₄₉NO₁₂
• 分子量: 928.005
• InChiKey: VDPIXQXVIMFASO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  69
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  7,8-dibenzyloxy-6-[3-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester 在 咪唑 、 selenium(IV) oxide 、 氢气 、 硼酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 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 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium dithionite 、 ammonium acetate 、 水 、 potassium carbonate 、 戴斯-马丁氧化剂 、 异氰酸苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 26.66h， 生成 7,8-dibenzyloxy-6-[3-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-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

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.