3-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1-tosyl-1H-pyrrolo[2,3-f] quinoline | 1533429-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1-tosyl-1H-pyrrolo[2,3-f] quinoline
• CAS: 1533429-87-6
• 化学式: C₂₈H₃₀N₄O₄S
• 分子量: 518.637
• InChiKey: LUFFWMXEEGULRL-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  95.14
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1-tosyl-1H-pyrrolo[2,3-f] quinoline 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以84%的产率得到methyl (S)-2-amino-3-(1-tosyl-1H-pyrrolo[2,3-f]quinolin-3-yl)propanoate
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

  摘要：

  Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schollkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

  DOI：

  10.1021/ol403429e
• 作为产物：
  描述：

  1H-pyrrolo[2,3-f]quinoline-3-carbaldehyde 在 sodium tetrahydroborate 、 正丁基锂 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 3-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1-tosyl-1H-pyrrolo[2,3-f] quinoline
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Tryptophan Analogues Having Useful Photophysical Properties

  摘要：

  Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Schollkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

  DOI：

  10.1021/ol403429e