6-(5-甲酰基-2-氧代-1,3-二氢咪唑-4-基)己酸乙酯 | 39215-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-(5-甲酰基-2-氧代-1,3-二氢咪唑-4-基)己酸乙酯
• 英文名称: ethyl 9-oxo-7,8-didehydrodethiobiotin
• 英文别名: 6-(5-formyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-hexanoic acid ethyl ester；Ethyl 6-(5-formyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)hexanoate；ethyl 6-(5-formyl-2-oxo-1,3-dihydroimidazol-4-yl)hexanoate
• CAS: 39215-48-0
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: IYRQTSLTETZKKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(5-甲酰基-2-氧代-1,3-二氢咪唑-4-基)己酸乙酯 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 ethyl N,N'-diacetyldidehydrodethiobiotin
  参考文献：
  名称：

  Synthesis and biological activity of 9-mercaptodethiobiotin—a putative biotin precursor in Escherichia coli

  摘要：

  A total synthesis of (+/-)-9-mercaptodethiobiotin 3 via the aldehyde 9 is described. Compound (+/-)-3 does not function as a biotin replacement factor for an E. coli mutant (SA291) lacking the entire biotin synthesis operon (bioABFCD-) but supports growth of an E. coli bioA mutant. Compound (+/-)-3 also supports growth of transformed cells of SA291 carrying a plasmid encoding the E. coli biotin synthase (bioB) gene indicating that the compound may be able to substitute for dethiobiotin 2 as a substrate for biotin synthase.

  DOI：

  10.1039/p19920000255
• 作为产物：
  描述：

  6-氯-6-氧代己酸乙酯 在 哌啶 、 sodium tetrahydroborate 、 三氯化铝 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 6-(5-甲酰基-2-氧代-1,3-二氢咪唑-4-基)己酸乙酯
  参考文献：
  名称：

  Synthesis and biological activity of 9-mercaptodethiobiotin—a putative biotin precursor in Escherichia coli

  摘要：

  A total synthesis of (+/-)-9-mercaptodethiobiotin 3 via the aldehyde 9 is described. Compound (+/-)-3 does not function as a biotin replacement factor for an E. coli mutant (SA291) lacking the entire biotin synthesis operon (bioABFCD-) but supports growth of an E. coli bioA mutant. Compound (+/-)-3 also supports growth of transformed cells of SA291 carrying a plasmid encoding the E. coli biotin synthase (bioB) gene indicating that the compound may be able to substitute for dethiobiotin 2 as a substrate for biotin synthase.

  DOI：

  10.1039/p19920000255