7,8-Bis-benzyloxy-6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxy-naphthalen-2-yl)-3-oxo-butyl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester | 908338-96-5

• 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-Bis-benzyloxy-6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxy-naphthalen-2-yl)-3-oxo-butyl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-yl)-3-oxobutyl]-1-oxo-7,8-bis(phenylmethoxy)isochromene-3-carboxylate；methyl 6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxynaphthalen-2-yl)-3-oxobutyl]-1-oxo-7,8-bis(phenylmethoxy)isochromene-3-carboxylate
• CAS: 908338-96-5
• 化学式: C₄₄H₄₂O₁₄
• 分子量: 794.809
• InChiKey: QAKCZLZOZKNAFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  58
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  7,8-Bis-benzyloxy-6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxy-naphthalen-2-yl)-3-oxo-butyl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以88%的产率得到7,8-Dihydroxy-6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxy-naphthalen-2-yl)-3-oxo-butyl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Investigation of a Convergent Route to Purpuromycin:  Benzofuran Formation vs Spiroketalization

  摘要：

  A mild and efficient [3+2] nitrile oxide/olefin cycloaddition allows coupling of the highly functionalized naphthalene and isocoumarin hemispheres of purpuromycin. A rationale of the inability of advanced keto alcohols to spirocyclize is presented based upon a systematic examination of the electronic factors present in these systems and suggests that the biosynthesis of purpuromycin does not proceed through open-chain intermediates.

  DOI：

  10.1021/ol061112j
• 作为产物：
  描述：

  7,8-dibenzyloxy-6-formyl-1-oxo-1H-isochromene-3-carboxylic acid methyl ester 在 镍 盐酸 、 甲醇 、 四甲基乙二胺 、 水 、 氢气 、 硼酸 、 异氰酸苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 132.0h， 生成 7,8-Bis-benzyloxy-6-[1-hydroxy-4-(3-hydroxy-1,4,5,6,8-pentamethoxy-naphthalen-2-yl)-3-oxo-butyl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Investigation of a Convergent Route to Purpuromycin:  Benzofuran Formation vs Spiroketalization

  摘要：

  A mild and efficient [3+2] nitrile oxide/olefin cycloaddition allows coupling of the highly functionalized naphthalene and isocoumarin hemispheres of purpuromycin. A rationale of the inability of advanced keto alcohols to spirocyclize is presented based upon a systematic examination of the electronic factors present in these systems and suggests that the biosynthesis of purpuromycin does not proceed through open-chain intermediates.

  DOI：

  10.1021/ol061112j

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.
• Investigation of a Convergent Route to Purpuromycin:  Benzofuran Formation vs Spiroketalization
  作者：Stephen P. Waters、Michael W. Fennie、Marisa C. Kozlowski

  DOI：10.1021/ol061112j

  日期：2006.7.1

  A mild and efficient [3+2] nitrile oxide/olefin cycloaddition allows coupling of the highly functionalized naphthalene and isocoumarin hemispheres of purpuromycin. A rationale of the inability of advanced keto alcohols to spirocyclize is presented based upon a systematic examination of the electronic factors present in these systems and suggests that the biosynthesis of purpuromycin does not proceed through open-chain intermediates.