6,8-dibromo-3-hydroxy-7-methoxy-coumarin | 863891-06-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6,8-dibromo-3-hydroxy-7-methoxy-coumarin
• 英文别名: 6,8-Dibromo-3-hydroxy-7-methoxy-；6,8-dibromo-3-hydroxy-7-methoxychromen-2-one
• CAS: 863891-06-9
• 化学式: C₁₀H₆Br₂O₄
• 分子量: 349.963
• InChiKey: RBIXLAQQPHGWSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.5±45.0 °C(Predicted)
• 密度：
  2.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-dibromo-3-hydroxy-7-methoxy-coumarin 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 生成 6,8-dibromo-7-methoxy-3-hydroximino-3,4-dihydrocoumarin 、 (2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-N-hydroxy-2-hydroxyiminopropanamide
  参考文献：
  名称：

  Efficient Synthesis of Tyrosine-Derived Marine Sponge Metabolites via Acylation of Amines with a Coumarin

  摘要：

  Condensation of N-acetylglycine with aldehyde 15 in acetic anhydride gave acetamido coumarin 16. Hydrolysis to the enol coumarin 17 and reaction with hydroxylamine gave the oximino coumarin 18. Reaction of the oximino coumarin 18 with a range of nucleophiles gave the phenolic oximes in excellent yield. The rates of acylation of histamine with the oximino coumarin 18 and methyl ester 9 were compared. Oxidative spirocyclization of three representative phenolic oximes with polymersupported (diacetoxyiodo) benzene gave the spiroisoxazolines.

  DOI：

  10.1021/jo050846r
• 作为产物：
  描述：

  3,5-二溴-2-羟基-4-甲氧基苯甲醛 在 盐酸 、 sodium acetate 、 乙酸酐 作用下， 以 乙醇 为溶剂， 生成 6,8-dibromo-3-hydroxy-7-methoxy-coumarin
  参考文献：
  名称：

  Efficient Synthesis of Tyrosine-Derived Marine Sponge Metabolites via Acylation of Amines with a Coumarin

  摘要：

  Condensation of N-acetylglycine with aldehyde 15 in acetic anhydride gave acetamido coumarin 16. Hydrolysis to the enol coumarin 17 and reaction with hydroxylamine gave the oximino coumarin 18. Reaction of the oximino coumarin 18 with a range of nucleophiles gave the phenolic oximes in excellent yield. The rates of acylation of histamine with the oximino coumarin 18 and methyl ester 9 were compared. Oxidative spirocyclization of three representative phenolic oximes with polymersupported (diacetoxyiodo) benzene gave the spiroisoxazolines.

  DOI：

  10.1021/jo050846r

文献信息

• Total syntheses of subereamollines A and B
  作者：James W. Shearman、Rebecca M. Myers、James D. Brenton、Steven V. Ley

  DOI：10.1039/c0ob00636j

  日期：——

  The first total syntheses of (+)- and (−)-subereamollines A and B are reported. The enantiomeric forms of the natural products were obtained by preparative chiral HPLC separation of the corresponding racemates.

  首次报道了(+)-和(−)-subereamollines A和B的完整合成。这些天然产物的对映体形式通过相应外消旋体的制备性手性高效液相色谱分离获得。
• Efficient Synthesis of Tyrosine-Derived Marine Sponge Metabolites via Acylation of Amines with a Coumarin
  作者：J. Jonathan Harburn、Nigam P. Rath、Christopher D. Spilling

  DOI：10.1021/jo050846r

  日期：2005.8.1

  Condensation of N-acetylglycine with aldehyde 15 in acetic anhydride gave acetamido coumarin 16. Hydrolysis to the enol coumarin 17 and reaction with hydroxylamine gave the oximino coumarin 18. Reaction of the oximino coumarin 18 with a range of nucleophiles gave the phenolic oximes in excellent yield. The rates of acylation of histamine with the oximino coumarin 18 and methyl ester 9 were compared. Oxidative spirocyclization of three representative phenolic oximes with polymersupported (diacetoxyiodo) benzene gave the spiroisoxazolines.