1,4-bis-(7,9-dibromo-8-methoxy-10-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carbonylamino)-butane | 66333-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1,4-bis-(7,9-dibromo-8-methoxy-10-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carbonylamino)-butane
• 英文别名: 7,9-dibromo-N-[4-[(7,9-dibromo-8-methoxy-6-oxo-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carbonyl)amino]butyl]-8-methoxy-6-oxo-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
• CAS: 66333-92-4
• 化学式: C₂₄H₂₂Br₄N₄O₈
• 分子量: 814.077
• InChiKey: XQDACPHHIARIQT-UHFFFAOYSA-N

物化性质

• 密度：
  2.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,4-bis-(7,9-dibromo-8-methoxy-10-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carbonylamino)-butane 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以25%的产率得到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：

  N,N'-bis<3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropionyl>-1,4-butanediamine 在 四溴环己二烯-1-酮 作用下， 以 乙腈 为溶剂， 生成 1,4-bis-(7,9-dibromo-8-methoxy-10-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,8-triene-3-carbonylamino)-butane
  参考文献：
  名称：

  Forrester,A.R. et al., Justus Liebigs Annalen der Chemie, 1978, p. 66 - 73

  摘要：

  DOI：

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.
• Forrester,A.R. et al., Justus Liebigs Annalen der Chemie, 1978, p. 66 - 73
  作者：Forrester,A.R. et al.

  DOI：——

  日期：——