3-(3,5-Dibromo-4-{9-bromo-3-[(E)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionic acid | 210880-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-(3,5-Dibromo-4-{9-bromo-3-[(E)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionic acid
• 英文别名: 3-[3,5-dibromo-4-[(7-bromo-3-hydroxyimino-2,8-dioxo-1-oxaspiro[4.5]deca-6,9-dien-9-yl)oxy]phenyl]-2-hydroxyiminopropanoic acid
• CAS: 210880-78-7
• 化学式: C₁₈H₁₁Br₃N₂O₈
• 分子量: 623.006
• InChiKey: BQOMKBNGYSAATF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  155.08
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-(3,5-Dibromo-4-{9-bromo-3-[(E)-hydroxyimino]-2,8-dioxo-1-oxa-spiro[4.5]deca-6,9-dien-7-yloxy}-phenyl)-2-[(E)-hydroxyimino]-propionic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 sodium hydrogensulfite 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.75h， 生成 3-[3-(4-{2-(2-{3-[4-(2-Amino-ethyl)-2,6-dibromo-phenoxy]-5-bromo-4-hydroxy-phenyl}-ethylcarbamoyl)-2-[(E)-hydroxyimino]-ethyl}-2,6-dibromo-phenoxy)-5-bromo-4-hydroxy-phenyl]-2-[(Z)-hydroxyimino]-propionic acid
  参考文献：
  名称：

  Total Synthesis of Bastadins 2, 3, and 6

  摘要：

  A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.

  DOI：

  10.1021/jo9721204
• 作为产物：
  描述：

  3-(3,5-二溴-4-羟基苯基)-2-(羟基亚氨基)丙酸 在 双氧水 、 soybean peroxidase 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以3%的产率得到7,9-Dibromo-8-oxo-1-oxa-2-aza-spiro[4.5]deca-2,6,9-triene-3-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of Bastadins 2, 3, and 6

  摘要：

  A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.

  DOI：

  10.1021/jo9721204