N-benzyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-benzyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanamide
• 英文别名: (2E)-N-benzyl-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanamide
• 化学式: C₁₇H₁₆Br₂N₂O₄
• 分子量: 472.133
• InChiKey: AIDBCFSKLAWYPX-FYJGNVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanamide 在 polymer-supported phenyliodine(III) diacetate 作用下， 以 乙腈 为溶剂， 以98%的产率得到N-benzyl-7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro[4,5]deca-2,7,9-triene-3-carbamide
  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：

  6,8-dibromo-7-methoxy-3-hydroximino-3,4-dihydrocoumarin 、 苄胺 以93%的产率得到N-benzyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2(E)-(hydroximino)propanamide
  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

• 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.