7-benzyloxy-6-[4-(3-benzyloxy-4,5,6,8-tetramethoxynaphthalen-2-yl)-1-hydroxy-3-oxobutyl]-8-methoxy-1-oxo-1Hisochromene-3-carboxylic acid methyl ester | 1315508-17-8

• 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-[4-(3-benzyloxy-4,5,6,8-tetramethoxynaphthalen-2-yl)-1-hydroxy-3-oxobutyl]-8-methoxy-1-oxo-1Hisochromene-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-[1-hydroxy-3-oxo-4-(4,5,6,8-tetramethoxy-3-phenylmethoxynaphthalen-2-yl)butyl]-8-methoxy-1-oxo-7-phenylmethoxyisochromene-3-carboxylate
• CAS: 1315508-17-8
• 化学式: C₄₄H₄₂O₁₃
• 分子量: 778.81
• InChiKey: NKVFKBGKWQQJED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  57
• 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：
  155
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-6-[4-(3-benzyloxy-4,5,6,8-tetramethoxynaphthalen-2-yl)-1-hydroxy-3-oxobutyl]-8-methoxy-1-oxo-1Hisochromene-3-carboxylic acid methyl ester 在 咪唑 、 selenium(IV) oxide 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 水 、 氢气 、 硼酸 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 99.0h， 生成 methyl 4-[tert-butyl(diphenyl)silyl]oxy-5',7',8',9'-tetramethoxy-9-oxo-10-propylsulfanylspiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-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
• 作为产物：
  描述：

  ethyl 3,4-dihydro-5,6,8-trimethoxy-3,4-dioxonaphthalene-2-carboxylate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium dithionite 、 ammonium acetate 、 水 、 氢气 、 硼酸 、 potassium carbonate 、 戴斯-马丁氧化剂 、 异氰酸苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 219.43h， 生成 7-benzyloxy-6-[4-(3-benzyloxy-4,5,6,8-tetramethoxynaphthalen-2-yl)-1-hydroxy-3-oxobutyl]-8-methoxy-1-oxo-1Hisochromene-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.