7-benzyloxy-6-[3-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-8-methoxy-1-oxo-1H-isochromene-3-carboxylic acid methyl ester | 1315507-91-5

• 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-benzyloxy-6-[3-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-8-methoxy-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-[3-[(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-yl)methyl]-4,5-dihydro-1,2-oxazol-5-yl]-8-methoxy-1-oxo-7-phenylmethoxyisochromene-3-carboxylate
• CAS: 1315507-91-5
• 化学式: C₃₈H₃₇NO₁₃
• 分子量: 715.711
• InChiKey: OPEBQWCGRAHDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-6-[3-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-8-methoxy-1-oxo-1H-isochromene-3-carboxylic acid methyl ester 在 氢气 、 硼酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.5h， 以96%的产率得到7-benzyloxy-6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-yl)-3-oxo-butyl]-8-methoxy-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：

  triethyl-[1,4,5,7,8-pentamethoxy-3-(2-nitro-ethyl)-naphthalen-2-yloxy]-silane 在 盐酸 、 异氰酸苯酯 、 三乙胺 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 44.5h， 生成 7-benzyloxy-6-[3-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-ylmethyl)-4,5-dihydroisoxazol-5-yl]-8-methoxy-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.