6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid | 530129-45-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid
• 英文别名: 6-[[5,6-dicyano-3-(diethylamino)pyrazin-2-yl]amino]hexanoic acid
• CAS: 530129-45-4
• 化学式: C₁₆H₂₂N₆O₂
• 分子量: 330.39
• InChiKey: LQBSITJIXLFRGE-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  638.0±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  125.93
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid 、 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile 在 lithium 、 正丁醇 作用下， 反应 3.0h， 以1.3%的产率得到2,3,9,10,16,17,23,24-octakis(diethylamino)-1,4,8,11,15,18,22,25-(octaaza)phthalocyanine
  参考文献：
  名称：

  Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers

  摘要：

  Mono-, di-, tri- and tetracarboxy-substituted metal-free azaphthalocyanines (AzaPc) were synthesized from 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile and 6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid using a statistical condensation approach. AzaPc bearing eight diethylamino peripheral substituents was also isolated from the mixture. Analysis of the distribution of congeners in the statistical mixture using optimized HPLC method (Phenomenex Synergy RP Fusion column, aceto-nitrile/tetrahydrofuran/water (pH 5.5) 50:20:30) was performed. The analysis showed optimal ratios of starting materials to be 3:1 for AAAB, 1:3 for ABBB and 1:1 for AABB/ABAB types of the congeners. The distribution of the congeners corresponded well with calculated values indicating similar reactivity of both starting materials and no sterical constraint between adjacent isoindole units in the AzaPc ring. All investigated AzaPc showed no fluorescence, extremely low singlet oxygen quantum yields (Phi(Delta) < 0.005) in monomeric form and strong absorption in a wide range from 300 nm to almost 700 nm. Such properties are highly promising for future investigation of these compounds as dark quenchers of fluorescence in DNA hybridization probes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.03.016
• 作为产物：
  描述：

  6-氨基己酸 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid
  参考文献：
  名称：

  Synthesis of mono-, di-, tri- and tetracarboxy azaphthalocyanines as potential dark quenchers

  摘要：

  Mono-, di-, tri- and tetracarboxy-substituted metal-free azaphthalocyanines (AzaPc) were synthesized from 5,6-bis(diethylamino)pyrazine-2,3-dicarbonitrile and 6-(5,6-dicyano-3-(diethylamino)pyrazin-2-ylamino)hexanoic acid using a statistical condensation approach. AzaPc bearing eight diethylamino peripheral substituents was also isolated from the mixture. Analysis of the distribution of congeners in the statistical mixture using optimized HPLC method (Phenomenex Synergy RP Fusion column, aceto-nitrile/tetrahydrofuran/water (pH 5.5) 50:20:30) was performed. The analysis showed optimal ratios of starting materials to be 3:1 for AAAB, 1:3 for ABBB and 1:1 for AABB/ABAB types of the congeners. The distribution of the congeners corresponded well with calculated values indicating similar reactivity of both starting materials and no sterical constraint between adjacent isoindole units in the AzaPc ring. All investigated AzaPc showed no fluorescence, extremely low singlet oxygen quantum yields (Phi(Delta) < 0.005) in monomeric form and strong absorption in a wide range from 300 nm to almost 700 nm. Such properties are highly promising for future investigation of these compounds as dark quenchers of fluorescence in DNA hybridization probes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.03.016