1,8-diamidinoanthracene | 1362737-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-diamidinoanthracene
• 英文别名: Anthracene-1,8-dicarboximidamide；anthracene-1,8-dicarboximidamide
• CAS: 1362737-64-1
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: BCCYKTHPFVKRSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.7
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-丁基磷酸 、 1,8-diamidinoanthracene 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  使用蒽基二di的单膦酸和二膦酸衍生物的开启荧光传感器及其对膦酸am和and的形成的检测

  摘要：

  使用基于蒽二脒二膦酸和单-膦酸衍生物的荧光检测1进行了研究。的二脒1种形式1：1和1：2个络合物分别与二膦酸和单-膦酸衍生物，并呈现出蓝色荧光（λ EM 中的DMSO溶液= 432-442纳米）。脒鎓膦酸酯（复合物形成）和离解amidinum的形成（λ EM  = 468纳米作为宽带）通过在荧光波长的差异区分，并且通过DOSY NMR光谱和TD-DFT计算证实。与二am 1形成1：2络合物 提出了在甲基膦酸之间具有另外的分子间氢键的甲基膦酸。

  DOI：

  10.1016/j.tet.2017.12.011
• 作为产物：
  描述：

  蒽-1,8-二腈 在 trimethylaluminum 、 氯化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 24.08h， 生成 1,8-diamidinoanthracene
  参考文献：
  名称：

  Fluorescent detection of amidinium–carboxylate and amidinium formation using anthracene-based diamidine: an application for the analysis of dicarboxylic acid binding

  摘要：

  An anthracene-based diamidine (1) 'turn-on' fluorescent probe for the detection of dicarboxylic acids has been designed and synthesized. The fluorescence spectra of the diamidine 1 with carboxylic acids that showed two different fluorescence bands, which corresponded to the amidinium-carboxylate (lambda(em)=430-440 nm), and amidinium (lambda(em)=460-470 nm as a broad band) formation, were confirmed by DOSY NMR and TD-DFT calculations. These different fluorescence bands showed the binding mode of carboxylic acids and the stability of formed complexes toward diamidine 1. The fluorescent detection of amidinium carboxylate formation using diamidine 1 was applicable to the detection of alpha,omega-dicarboxylic acids (C-6-C-13) and succeeded in the detection of alpha,omega-dicarboxylic acid (adipic acid) in human urine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.072

文献信息

• Recognition of dicarboxylic acids and diphosphonic acids using anthracene-based diamidine: formation of amidinium-carboxylate and amidinium-phosphonate salt bridges in a protic solvent
  作者：Takahiro Kusukawa、Keita Nakaguchi、Saya Nishimura、Akane Nakajima

  DOI：10.1080/10610278.2021.1908545

  日期：2021.3.4

  ABSTRACT The formation of a stable ‘amidinium-carboxylate’ salt bridge, even in a competing protic solvent (MeOH), was observed based on the binding experiments of anthracene-based diamidine (1) and dicarboxylic acids. The formation of 1:1 binding complexes of the diamidine 1 and dicarboxylic acids was confirmed by DOSY NMR, ESI-Mass, titration experiments and a single crystal X-ray analysis. Similarly

  摘要 基于蒽基二脒 ( 1 ) 和二羧酸的结合实验，观察到稳定的“脒-羧酸盐”盐桥的形成，即使在竞争性质子溶剂 (MeOH) 中也是如此。通过 DOSY NMR、ESI-Mass、滴定实验和单晶 X 射线分析证实了二脒1和二羧酸的 1:1 结合复合物的形成。类似地，二脒1和二膦酸的络合也证明了 MeOH 溶液中“脒-膦酸盐”盐桥的形成。
• Turn-on fluorescence sensor for mono- and di-phosphonic acid derivatives using anthracene-based diamidine and its detection of amidinium-phosphonate and amidinium formation
  作者：Takahiro Kusukawa、Hitoshi Nagano、Keita Nakaguchi、Shota Takeshita、Yuya Harumoto

  DOI：10.1016/j.tet.2017.12.011

  日期：2018.1

  di-phosphonic acid and mono-phosphonic acid derivatives using the anthracene-based diamidine 1 has been investigated. The diamidine 1 forms 1:1 and 1:2 complexes with the di-phosphonic acid and mono-phosphonic acid derivatives, respectively, and showed a blue fluorescence (λem = 432–442 nm) in a DMSO solution. The formation of amidinium-phosphonate (complex formation) and dissociated amidinum (λem = 468 nm as a

  使用基于蒽二脒二膦酸和单-膦酸衍生物的荧光检测1进行了研究。的二脒1种形式1：1和1：2个络合物分别与二膦酸和单-膦酸衍生物，并呈现出蓝色荧光（λ EM 中的DMSO溶液= 432-442纳米）。脒鎓膦酸酯（复合物形成）和离解amidinum的形成（λ EM  = 468纳米作为宽带）通过在荧光波长的差异区分，并且通过DOSY NMR光谱和TD-DFT计算证实。与二am 1形成1：2络合物 提出了在甲基膦酸之间具有另外的分子间氢键的甲基膦酸。
• Fluorescent detection of amidinium–carboxylate and amidinium formation using anthracene-based diamidine: an application for the analysis of dicarboxylic acid binding
  作者：Takahiro Kusukawa、Keisuke Toyama、Shota Takeshita、Syugo Tanaka

  DOI：10.1016/j.tet.2012.09.072

  日期：2012.12

  An anthracene-based diamidine (1) 'turn-on' fluorescent probe for the detection of dicarboxylic acids has been designed and synthesized. The fluorescence spectra of the diamidine 1 with carboxylic acids that showed two different fluorescence bands, which corresponded to the amidinium-carboxylate (lambda(em)=430-440 nm), and amidinium (lambda(em)=460-470 nm as a broad band) formation, were confirmed by DOSY NMR and TD-DFT calculations. These different fluorescence bands showed the binding mode of carboxylic acids and the stability of formed complexes toward diamidine 1. The fluorescent detection of amidinium carboxylate formation using diamidine 1 was applicable to the detection of alpha,omega-dicarboxylic acids (C-6-C-13) and succeeded in the detection of alpha,omega-dicarboxylic acid (adipic acid) in human urine. (C) 2012 Elsevier Ltd. All rights reserved.