methyl 7,8-bis(benzyloxy)-6-(3-(3-(benzyloxy)-1,4,5,6,8-pentamethoxy-2-naphthoyl)-4,5-dihydroisoxazol-5-yl)-1-oxo-1H-isochromene-3-carboxylate | 1315507-97-1

• 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: methyl 7,8-bis(benzyloxy)-6-(3-(3-(benzyloxy)-1,4,5,6,8-pentamethoxy-2-naphthoyl)-4,5-dihydroisoxazol-5-yl)-1-oxo-1H-isochromene-3-carboxylate
• 英文别名: Methyl 1-oxo-6-[3-(1,4,5,6,8-pentamethoxy-3-phenylmethoxynaphthalene-2-carbonyl)-4,5-dihydro-1,2-oxazol-5-yl]-7,8-bis(phenylmethoxy)isochromene-3-carboxylate
• CAS: 1315507-97-1
• 化学式: C₅₁H₄₅NO₁₄
• 分子量: 895.917
• InChiKey: NDZIWVYNDHLURJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  66
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  7,8-dibenzyloxy-1-oxo-6-vinyl-1H-isochromene-3-carboxylic acid methyl ester 、 1-(2-(benzyloxy)-1,4,5,7,8-pentamethoxynaphthalen-3-yl)-2-nitroethanone 在 异氰酸苯酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 48.0h， 以56%的产率得到methyl 7,8-bis(benzyloxy)-6-(3-(3-(benzyloxy)-1,4,5,6,8-pentamethoxy-2-naphthoyl)-4,5-dihydroisoxazol-5-yl)-1-oxo-1H-isochromene-3-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

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.