2,2-Difluoro-12-hept-6-enyl-4,6-dimethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene | 1226949-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,2-Difluoro-12-hept-6-enyl-4,6-dimethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1226949-14-9
• 化学式: C₁₈H₂₃BF₂N₂
• 分子量: 316.202
• InChiKey: JTAXDZVPDJCHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Difluoro-12-hept-6-enyl-4,6-dimethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene 、 (S)-tert-butyl(dimethyl)(2,5,7,8-tetramethyl-2-vinylchroman-6-yloxy)silane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到
  参考文献：
  名称：

  Synthesis and Characterization of BODIPY-α-Tocopherol: A Fluorescent Form of Vitamin E

  摘要：

  Fluorescent nitrobenzoxadiazole analogues of alpha-tocopherol (NBD-alpha-Tocs;lambda(ex) = 468 nm, lambda(em) = 527 nm) have been made previously to aid study of the intracellular location and transfer of vitamin E. However, these analogues are susceptible to photobleaching while under illumination for confocal microscopy as well as in in vitro FRET transfer assays. Here we report the synthesis of three fluorescent analogues of alpha-tocopherol incorporating the more robust dipyrrometheneboron difluoride (BODIPY) fluorophore. A BODIPY-linked chromanol should have no intervening polar functional groups that might interfere with binding to the hydrophobic binding site of the tocopherol transfer protein (alpha-TTP). A key step in bringing the two ring systems together was a metathesis reaction of vinyl chromanol and an alkenyl BODIPY. An o-tolyl containing second generation Grubbs catalyst was identified as the best catalyst for effecting the metathesis without detectable alkene isomerization, which when it occurred produced a mixture of chain lengths in the alkyl linker. C8-BODIPY-alpha-Toc 10c (lambda(ex) = 507 nm, lambda(em) = 511 nm, epsilon(507) = 83,000 M-1 cm(-1)) having an eight-carbon chain between the chromanol and fluorophore, had the highest affinity for alpha-TTP (K-d = 94 +/- 3 nM) and bound specifically as it could not be displaced with cholesterol.

  DOI：

  10.1021/jo100095n
• 作为产物：
  描述：

  3,5-二甲基-2-吡咯甲醛 、 2-(hept-6-enyl)-1H-pyrrole 在 三氯氧磷 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以34%的产率得到2,2-Difluoro-12-hept-6-enyl-4,6-dimethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
  参考文献：
  名称：

  Synthesis and Characterization of BODIPY-α-Tocopherol: A Fluorescent Form of Vitamin E

  摘要：

  Fluorescent nitrobenzoxadiazole analogues of alpha-tocopherol (NBD-alpha-Tocs;lambda(ex) = 468 nm, lambda(em) = 527 nm) have been made previously to aid study of the intracellular location and transfer of vitamin E. However, these analogues are susceptible to photobleaching while under illumination for confocal microscopy as well as in in vitro FRET transfer assays. Here we report the synthesis of three fluorescent analogues of alpha-tocopherol incorporating the more robust dipyrrometheneboron difluoride (BODIPY) fluorophore. A BODIPY-linked chromanol should have no intervening polar functional groups that might interfere with binding to the hydrophobic binding site of the tocopherol transfer protein (alpha-TTP). A key step in bringing the two ring systems together was a metathesis reaction of vinyl chromanol and an alkenyl BODIPY. An o-tolyl containing second generation Grubbs catalyst was identified as the best catalyst for effecting the metathesis without detectable alkene isomerization, which when it occurred produced a mixture of chain lengths in the alkyl linker. C8-BODIPY-alpha-Toc 10c (lambda(ex) = 507 nm, lambda(em) = 511 nm, epsilon(507) = 83,000 M-1 cm(-1)) having an eight-carbon chain between the chromanol and fluorophore, had the highest affinity for alpha-TTP (K-d = 94 +/- 3 nM) and bound specifically as it could not be displaced with cholesterol.

  DOI：

  10.1021/jo100095n

文献信息

• Synthesis and Characterization of BODIPY-α-Tocopherol: A Fluorescent Form of Vitamin E
  作者：Ryan West、Candace Panagabko、Jeffrey Atkinson

  DOI：10.1021/jo100095n

  日期：2010.5.7

  Fluorescent nitrobenzoxadiazole analogues of alpha-tocopherol (NBD-alpha-Tocs;lambda(ex) = 468 nm, lambda(em) = 527 nm) have been made previously to aid study of the intracellular location and transfer of vitamin E. However, these analogues are susceptible to photobleaching while under illumination for confocal microscopy as well as in in vitro FRET transfer assays. Here we report the synthesis of three fluorescent analogues of alpha-tocopherol incorporating the more robust dipyrrometheneboron difluoride (BODIPY) fluorophore. A BODIPY-linked chromanol should have no intervening polar functional groups that might interfere with binding to the hydrophobic binding site of the tocopherol transfer protein (alpha-TTP). A key step in bringing the two ring systems together was a metathesis reaction of vinyl chromanol and an alkenyl BODIPY. An o-tolyl containing second generation Grubbs catalyst was identified as the best catalyst for effecting the metathesis without detectable alkene isomerization, which when it occurred produced a mixture of chain lengths in the alkyl linker. C8-BODIPY-alpha-Toc 10c (lambda(ex) = 507 nm, lambda(em) = 511 nm, epsilon(507) = 83,000 M-1 cm(-1)) having an eight-carbon chain between the chromanol and fluorophore, had the highest affinity for alpha-TTP (K-d = 94 +/- 3 nM) and bound specifically as it could not be displaced with cholesterol.