7,8-Bis-benzyloxy-6-[3-(2-benzyloxy-benzyl)-4,5-dihydro-isoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester | 908339-01-5

• 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-[3-(2-benzyloxy-benzyl)-4,5-dihydro-isoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 1-oxo-7,8-bis(phenylmethoxy)-6-[3-[(2-phenylmethoxyphenyl)methyl]-4,5-dihydro-1,2-oxazol-5-yl]isochromene-3-carboxylate；methyl 1-oxo-7,8-bis(phenylmethoxy)-6-[3-[(2-phenylmethoxyphenyl)methyl]-4,5-dihydro-1,2-oxazol-5-yl]isochromene-3-carboxylate
• CAS: 908339-01-5
• 化学式: C₄₂H₃₅NO₈
• 分子量: 681.742
• InChiKey: BBZQYVFJBPZNFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7,8-Bis-benzyloxy-6-[3-(2-benzyloxy-benzyl)-4,5-dihydro-isoxazol-5-yl]-1-oxo-1H-isochromene-3-carboxylic acid methyl ester 在 palladium on activated charcoal 、 镍 水 、 氢气 、 硼酸 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.75h， 生成 6-(2-Benzofuran-2-yl-1-hydroxy-ethyl)-7,8-dihydroxy-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 四甲基乙二胺 、 异氰酸苯酯 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 反应 86.0h， 生成 7,8-Bis-benzyloxy-6-[3-(2-benzyloxy-benzyl)-4,5-dihydro-isoxazol-5-yl]-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

• 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.