8-[4-(5-aminopyrazin-2-yl)phenyl]-2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene | 1207336-31-9

• 英文名称: 8-[4-(5-aminopyrazin-2-yl)phenyl]-2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• CAS: 1207336-31-9
• 化学式: C₂₇H₃₀BF₂N₅
• 分子量: 473.377
• InChiKey: WBSMUOUGYDJPAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  8-[4-(5-aminopyrazin-2-yl)phenyl]-2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 、 乙酸酐 在 吡啶 作用下， 反应 216.0h， 以80%的产率得到2-acetamido-5-[4-(2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl)phenyl]pyrazine
  参考文献：
  名称：

  Synthesis of boradiazaindacene–imidazopyrazinone conjugate as lipophilic and yellow-chemiluminescent chemosensor for superoxide radical anion

  摘要：

  As a chemiluminescent chemosensor that emits yellow light on reacting with a superoxide radical anion (O(2)(center dot-)) and has a lipophilic character, a 6-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivative possessing a boradiazaindacene (BODIPY) at the para position of 6-phenyl (1) was synthesized. The lipophilicity of 1 was investigated by reversed-phase liquid chromatography, and its log P(ow) value was found to be 3.57. This value was Much higher than that of 2-methyl-6-(4-methoxypheyl)imidazo [ 1,2-a]pyrazin-3(7H)-one (MCLA, log P(ow)=1.19) and 6-[4-[2-{N'-(5-fluoresceinyl)thioureido}ethoxy]phenyl]-2-methylimidazo[1,2-a]pyrazin-3(7H)-one (FCLA, log P(ow)=-0.08), and it was comparable to that of benzenoid hydrocarbons. The O(2)(center dot-)-induced chemiluminescence of 1 was investigated using the hypoxanthine/xanthine oxidase system as the source of O(2)(center dot-), and as a result, yellow emission was observed. The maximum wavelength was observed at 542 nm, and it was longer than that of FCLA. (C) 2009 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.086
• 作为产物：
  描述：

  在 N,N-二异丙基乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以5.2 mg的产率得到8-[4-(5-aminopyrazin-2-yl)phenyl]-2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis of boradiazaindacene–imidazopyrazinone conjugate as lipophilic and yellow-chemiluminescent chemosensor for superoxide radical anion

  摘要：

  As a chemiluminescent chemosensor that emits yellow light on reacting with a superoxide radical anion (O(2)(center dot-)) and has a lipophilic character, a 6-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivative possessing a boradiazaindacene (BODIPY) at the para position of 6-phenyl (1) was synthesized. The lipophilicity of 1 was investigated by reversed-phase liquid chromatography, and its log P(ow) value was found to be 3.57. This value was Much higher than that of 2-methyl-6-(4-methoxypheyl)imidazo [ 1,2-a]pyrazin-3(7H)-one (MCLA, log P(ow)=1.19) and 6-[4-[2-{N'-(5-fluoresceinyl)thioureido}ethoxy]phenyl]-2-methylimidazo[1,2-a]pyrazin-3(7H)-one (FCLA, log P(ow)=-0.08), and it was comparable to that of benzenoid hydrocarbons. The O(2)(center dot-)-induced chemiluminescence of 1 was investigated using the hypoxanthine/xanthine oxidase system as the source of O(2)(center dot-), and as a result, yellow emission was observed. The maximum wavelength was observed at 542 nm, and it was longer than that of FCLA. (C) 2009 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.086