7-benzyloxy-8-methoxy-1-oxo-6-vinyl-1H-isochromene-3-carboxylic acid methyl ester | 1242170-09-7

• 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-8-methoxy-1-oxo-6-vinyl-1H-isochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-ethenyl-8-methoxy-1-oxo-7-phenylmethoxyisochromene-3-carboxylate
• CAS: 1242170-09-7
• 化学式: C₂₁H₁₈O₆
• 分子量: 366.37
• InChiKey: IZVRALDCJIBNBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-8-methoxy-1-oxo-6-vinyl-1H-isochromene-3-carboxylic acid methyl ester 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
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以0.346 g的产率得到7-benzyloxy-8-methoxy-1-oxo-6-vinyl-1H-isochromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  差异保护的香豆素的合成

  摘要：

  概述了适合完成嘌呤霉素的异香豆素亚基的合成。具体地，描述了针对正交保护的异香豆素（最终在12个步骤中产率为12％）和对称保护的异香豆素的改进合成（在10个步骤中为18％）的工作。还介绍了由碳酸氢钾介导的选择性儿茶酚保护的新修饰，以及对异香豆素的氧化和还原功能化的见解。

  DOI：

  10.1016/j.tet.2010.05.077

文献信息

• Syntheses of differentially protected isocoumarins
  作者：Andrew N. Lowell、Philip D. Wall、Stephen P. Waters、Marisa C. Kozlowski

  DOI：10.1016/j.tet.2010.05.077

  日期：2010.7

  Syntheses of an isocoumarin subunit suitable for the completion of purpuromycin are outlined. Specifically, work targeting an orthogonally protected isocoumarin (eventually 12% yield over 12 steps) and an improved synthesis of a symmetrically protected isocoumarin (18% over 10 steps) are described. A new modification for selective catechol protection as mediated by potassium bicarbonate is also presented

  概述了适合完成嘌呤霉素的异香豆素亚基的合成。具体地，描述了针对正交保护的异香豆素（最终在12个步骤中产率为12％）和对称保护的异香豆素的改进合成（在10个步骤中为18％）的工作。还介绍了由碳酸氢钾介导的选择性儿茶酚保护的新修饰，以及对异香豆素的氧化和还原功能化的见解。
• 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.