(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-N-[4-[[(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]butyl]-2-hydroxyiminopropanamide | 28687-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-N-[4-[[(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]butyl]-2-hydroxyiminopropanamide
• CAS: 28687-76-5
• 化学式: C₂₄H₂₆Br₄N₄O₈
• 分子量: 818.108
• InChiKey: FQIIUPRHOFOBOR-IHXWQEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-N-[4-[[(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]butyl]-2-hydroxyiminopropanamide 在 四溴环己二烯-1-酮 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.33h， 生成 aerothionin
  参考文献：
  名称：

  Syntheses of the Marine Metabolites Verongamine, Hemibastadin-2, and Aerothionin Using the Cyano Ylide Coupling Methodology

  摘要：

  Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin have been accomplished by a methodology involving the conversion of a carboxylic acid to an acyl cyano phosphorane which may be oxidized to an alpha,beta-diketo nitrile. This strongly electrophilic intermediate is rapidly converted by amines to alpha-keto amides.

  DOI：

  10.1021/jo980860m
• 作为产物：
  描述：

  2-(4-甲氧基-2-苯基甲氧基苯基)乙酸甲酯 在 palladium on activated charcoal sodium hydroxide 、 18-冠醚-6 、 盐酸羟胺 、 氢气 、 sodium acetate 、 pyridinium hydrobromide perbromide 、 四丁基碘化铵 、 臭氧 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 2.0~78.0 ℃ 、101.33 kPa 条件下， 反应 21.91h， 生成 (2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-N-[4-[[(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]butyl]-2-hydroxyiminopropanamide
  参考文献：
  名称：

  Syntheses of the Marine Metabolites Verongamine, Hemibastadin-2, and Aerothionin Using the Cyano Ylide Coupling Methodology

  摘要：

  Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin have been accomplished by a methodology involving the conversion of a carboxylic acid to an acyl cyano phosphorane which may be oxidized to an alpha,beta-diketo nitrile. This strongly electrophilic intermediate is rapidly converted by amines to alpha-keto amides.

  DOI：

  10.1021/jo980860m

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.
• Syntheses of the Marine Metabolites Verongamine, Hemibastadin-2, and Aerothionin Using the Cyano Ylide Coupling Methodology
  作者：Harry H. Wasserman、Jianji Wang

  DOI：10.1021/jo980860m

  日期：1998.8.1

  Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin have been accomplished by a methodology involving the conversion of a carboxylic acid to an acyl cyano phosphorane which may be oxidized to an alpha,beta-diketo nitrile. This strongly electrophilic intermediate is rapidly converted by amines to alpha-keto amides.