Methyl 2-bromo-8-cyclopropyl-7-[2-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)ethyl]-5-oxo-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate | 1487159-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2-bromo-8-cyclopropyl-7-[2-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)ethyl]-5-oxo-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
• CAS: 1487159-27-2
• 化学式: C₂₇H₂₇BBrF₂N₃O₃S
• 分子量: 602.307
• InChiKey: PFDYIHATHWIAEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-oxo-8-cyclopropyl-7-(2-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)ethyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 在 甲醇 、 三氯溴甲烷 、 sodium hydride 作用下， 以 乙腈 为溶剂， 生成 Methyl 2-bromo-8-cyclopropyl-7-[2-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)ethyl]-5-oxo-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Fluorescent Ring-Fused 2-Pyridone Peptidomimetics

  摘要：

  Thiazolino fused 2-pyridone peptidomimetics are of significant biological importance due to their ability to interfere with adhesive fiber formation in uropathogenic Escherichia coli and oligomerization of amyloid fibers. We have developed an efficient synthetic route to fluorescent BODIPY analogues, with structural diversification from a key intermediate enabling introduction of C-2 substituents and late incorporation of the BODIPY moiety. A mild lithium halide mediated hydrolysis enabled preparation of peptidomimetic fluorophores with useful photophysical properties for further chemical biology applications.

  DOI：

  10.1021/jo401844y