2-[3-(aminomethyl)benzylamino]-4-butylamino-6-diethylamino-1,3,5-triazine | 160155-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-[3-(aminomethyl)benzylamino]-4-butylamino-6-diethylamino-1,3,5-triazine
• 英文别名: 2-[3-(aminomethyl)benzylamino]-4-butylamino-6-diethylamino-s-triazine；2-butylamino-4-diethylamino-6-(3-aminomethylbenzylamino)-s-triazine
• CAS: 160155-67-9
• 化学式: C₁₉H₃₁N₇
• 分子量: 357.502
• InChiKey: QTAWEQPOSCWKBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  91.99
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  S-乙基异硫脲氢溴酸盐 、 2-[3-(aminomethyl)benzylamino]-4-butylamino-6-diethylamino-1,3,5-triazine 在 sodium perchlorate 作用下， 生成 2-[[3-[[[4-(Butylamino)-6-(diethylamino)-1,3,5-triazin-2-yl]amino]methyl]phenyl]methyl]guanidine;perchloric acid
  参考文献：
  名称：

  A flavin receptor. Strong binding ability of a melamine derivative bearing a guanidinium ion for 6-azaflavin: five hydrogen bonds formed in chloroform

  摘要：

  带有胍离子的三聚氰胺衍生物通过五个氢键与 6-氮杂黄素牢固结合，在 CHCl3 中结合常数为 140 000 mol–1 dm3。

  DOI：

  10.1039/c39940002583
• 作为产物：
  描述：

  2-butylamino-4-diethylamino-6-(3-ethoxycarbonylaminomethylbenzylamino)-s-triazine 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以95%的产率得到2-[3-(aminomethyl)benzylamino]-4-butylamino-6-diethylamino-1,3,5-triazine
  参考文献：
  名称：

  A flavin receptor. Strong binding ability of a melamine derivative bearing a guanidinium ion for 6-azaflavin: five hydrogen bonds formed in chloroform

  摘要：

  带有胍离子的三聚氰胺衍生物通过五个氢键与 6-氮杂黄素牢固结合，在 CHCl3 中结合常数为 140 000 mol–1 dm3。

  DOI：

  10.1039/c39940002583

文献信息

• Flavin Receptors. Effect of the Acidity of Melamine Derivatives Bearing a 2-Arylguanidinium Ion on 6-Azaflavin Binding in Chloroform
  作者：Hideki Moriya、Takeshi Kajiki、Shigeki Watanabe、Shin-ichi Kondo、Yumihiko Yano

  DOI：10.1246/bcsj.73.2539

  日期：2000.11

  The pKa's of melamine derivatives bearing a 2-arylguanidinium ion and their binding constants for 6-aza-10-dodecylisoalloxazine (6-azaflavin) were nicely correlated with the Hammett σ of the substituents. However, the rates of the oxidations of N-benzyl-1,4-dihydronicotinamide (BNAH) and dithiothreitol (DTT) by 6-azaflavin were not affected by the substituents of the receptors in CHCl3.

  带有2-芳基氨基脲离子的三聚氰胺衍生物的pKa值及其与6-氮杂-10-十二烷基异黄酮（6-氮杂黄素）的结合常数与取代基的HammeTT σ值之间呈良好的相关性。然而，在CHCl3中，6-氮杂黄素氧化N-苄基-1,4-二氢烟酰胺（BNAH）和二硫苏糖醇（DTT）的速率并未受到受体取代基的影响。
• Flavin Receptors. Effects of Melamine Derivatives Bearing Thiourea and Thiouronium Ion on the Binding and Reactivity of Flavin Mimics in Chloroform
  作者：Shigeki Watanabe、Naoki Kosaka、Shin-ichi Kondo、Yumihiko Yano

  DOI：10.1246/bcsj.77.569

  日期：2004.3

  Melamine derivatives bearing thiourea and thiouronium ion were prepared as flavin receptors. The binding modes of the receptors for flavin mimics were evaluated from the binding constants and 1H NMR data in chloroform. The effects of the receptors on the oxidation of N-benzyl-1,4-dihydronicotinamide (BNAH) and benzenethiol by flavin mimics were kinetically investigated in chloroform.

  制备了含有硫脲和硫脲离子的三聚氰胺衍生物作为黄素受体。根据结合常数和氯仿中的 1H NMR 数据，评估了受体与黄素模拟物的结合模式。在氯仿中，研究了受体对黄素模拟物氧化 N-苄基-1,4-二氢烟酰胺（BNAH）和苯硫酚的影响。
• Remarkable stabilization of the anionic semiquinone radical of 6-azaflavin by hydrogen bonding with a receptor in chloroform
  作者：Takeshi Kajiki、Hideki Moriya、Shin-ichi Kondo、Yumihiko Yano

  DOI：10.1039/a807737a

  日期：——

  An anionic semiquinone radical of 6-azaflavin (6-AzaFl) was found to be stabilized by hydrogen bonding of a melamine derivative bearing an N-phenylguanidinium ion in CHCl3, but not by the correponding N-unsubstituted guanidinium ion.

  研究发现，6-氮杂黄素（6-AzaFl）的阴离子半醌基在 CHCl3 中能通过含有 N-苯基胍离子的三聚氰胺衍生物的氢键而稳定，但不能通过相应的 N-未取代胍离子而稳定。
• Functionalized Flavin Receptors. Regulation of Redox Properties of 6-Azaflavin via Hydrogen Bondings with Melamine Derivatives Bearing Guanidinium Ion(s) in Organic Solvents
  作者：Takeshi Kajiki、Hideki Moriya、Kazuhiko Hoshino、Tadashi Kuroi、Shin-ichi Kondo、Tatsuya Nabeshima、Yumihiko Yano

  DOI：10.1021/jo9913210

  日期：1999.12.1

  Melamine derivatives bearing guanidinium ion(s) were synthesized as a flavin receptor using hydrogen bonds. The receptors bind 6-aza-10-dodecylisoalloxazine (6-azaflavin, 6-AzaFl) quite strongly via five or seven hydrogen bonds in CHCl3 or CHCl3-MeCN. Redox potentials of 6-AzaFl were considerably affected by hydrogen bondings of the receptors (positive shift: Delta E-1/2 = 220-317 mV). Anionic semiquinone radical of 6-AzaFl was found to be stabilized by hydrogen bondings with a melamine derivative bearing an N-phenylguanidinium ion or two guanidinium ions. Effects of the hydrogen bondings on the oxidation activity of 6-AzaFl were kinetically investigated for the oxidation of N-benzyl-1,4-dihydronicotinamide (BNAH) and PhSH in CHCl3-MeCN under anaerobic conditions. It was found that the N(1)-hydrogen bonding facilitates a slight BNAH oxidation (<10-fold) and the N(5)-hydrogen bonding remarkably accelerates the rate of PhSH oxidation (10(3)-10(4)-fold).