N,N′,N″-Tris(6-methoxy-2-quinolylmethyl)-1,4,7-triazacyclononane | 916431-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N′,N″-Tris(6-methoxy-2-quinolylmethyl)-1,4,7-triazacyclononane
• 英文别名: N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)ethylenediamine；6-MeOTQTACN；N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)-ethylenediamine；N,N,N',N'-tetrakis[(6-methoxyquinolin-2-yl)methyl]ethane-1,2-diamine
• CAS: 916431-27-1
• 化学式: C₄₆H₄₄N₆O₄
• 分子量: 744.893
• InChiKey: AHLMOKHJFBXJAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  zinc perchlorate 、 N,N′,N″-Tris(6-methoxy-2-quinolylmethyl)-1,4,7-triazacyclononane 以 乙腈 为溶剂， 以68%的产率得到[Zn(N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)ethylenediamine)](ClO4)2
  参考文献：
  名称：

  Methoxy-Substituted TQEN Family of Fluorescent Zinc Sensors

  摘要：

  Two methoxy-substituted TQEN (N,N,N ',N '-tetrakis(2-quinolylmethyl) ethylenediamine) derivatives, T(MQ)EN(N,N,N ',N '-tetrakis(6-methoxy-2-quinolylmethyl)ethylenediamine) and T(TMQ)EN (N,N,N ',N '-tetrakis(5,6,7-trimethoxy-2-quinolylmethyl) ethylenediamine), have been prepared, and their fluorescence properties with respect to Zn2+ coordination were investigated. Introduction of a methoxy substituent at 6-position of the quinoline ring enhances the fluorescence intensity by 10-fold, and the three methoxy substituents in the 5,6,7-positions afford significant enhancement of the long-wavelength component of the fluorescence of zinc complex. The substituents did not alter the binding affinity of these compounds toward zinc ion significantly. T(MQ)EN was proved to be effective in detection of zinc ion in cells by fluorescent microscopy.

  DOI：

  10.1021/ic060810x
• 作为产物：
  描述：

  乙二胺 、 2-(bromomethyl)-6-methoxyquinoline 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以33%的产率得到N,N′,N″-Tris(6-methoxy-2-quinolylmethyl)-1,4,7-triazacyclononane
  参考文献：
  名称：

  Fluorescent zinc ion sensor

  摘要：

  由以下一般式（I）表示的化合物或其盐：其中R1、R2、R3和R4分别表示可被取代的2-喹啉基团、可被取代的1-异喹啉基团或可被取代的3-异喹啉基团；m、n、p和q独立地表示1或2；L表示单键，或具有1至5个碳原子的烷基基团，其中该烷基基团可能在主链中含有一个或多个杂原子，并且可能在主链上具有一个或多个取代基，该化合物可用作荧光锌离子传感器。

  公开号：

  US20050182253A1

文献信息

• Quinoline-attached triazacyclononane (TACN) derivatives as fluorescent zinc sensors
  作者：Yuji Mikata、Yuki Nodomi、Asako Kizu、Hideo Konno

  DOI：10.1039/c3dt52107a

  日期：——

  TACN (1,4,7-triazacyclononane) derivatives with three 6-methoxy-2-quinolylmethyl or 1-isoquinolylmethyl moieties were examined as fluorescent zinc sensors. Upon the addition of zinc, 6-MeOTQTACN (5) exhibited a 9-fold fluorescence increase at 420 nm (λex = 341 nm, ϕZn = 0.070). Fluorescence enhancement is specific for zinc and cadmium, although cadmium induces smaller increases (ICd/I0 = 3.6 and ICd/IZn = 40%). The isoquinoline analog 1-isoTQTACN (6) exhibits minimal fluorescence enhancement upon zinc binding. TPEN (N,N,N′,N′-tetrakis(2-pyridylmethyl)ethylene-diamine) does not extract zinc from the 6-MeOTQTACN-Zn complex (5-Zn). The quantum yield, metal ion selectivity and metal binding affinity differences between TACN and ethylenediamine (EN) skeletons in quinoline-based ligands are discussed based on the X-ray crystallographic analysis of zinc and cadmium complexes, demonstrating the superiority of quinoline–TACN conjugates.

  TACN（1,4,7-三唑环诺烷）衍生物中含有三个6-甲氧基-2-喹啉甲基或1-异喹啉甲基基团，作为发光锌传感器进行研究。在加入锌后，6-甲氧基TQTACN（5）在420 nm处表现出9倍的荧光增强（λex = 341 nm，ϕZn = 0.070）。荧光增强对锌和镉是特异的，尽管镉诱导的增强较小（ICd/I0 = 3.6，ICd/IZn = 40%）。异喹啉类似物1-异TQTACN（6）在锌结合时几乎没有荧光增强。TPEN（N,N,N′,N′-四（2-吡啶甲基）乙烯二胺）不能从6-甲氧基TQTACN-Zn复合物（5-Zn）中提取锌。基于锌和镉复合物的X射线晶体分析，讨论了TACN和乙烯二胺（EN）框架在喹啉基配体中的量子产率、金属离子选择性和金属结合亲和力的差异，显示了喹啉–TACN共轭物的优越性。
• US7541467B2
  申请人：——

  公开号：US7541467B2

  公开（公告）日：2009-06-02
• Methoxy-Substituted TQEN Family of Fluorescent Zinc Sensors
  作者：Yuji Mikata、Motoko Wakamatsu、Ayano Kawamura、Natsuko Yamanaka、Shigenobu Yano、Akira Odani、Kazuko Morihiro、Satoshi Tamotsu

  DOI：10.1021/ic060810x

  日期：2006.11.1

  Two methoxy-substituted TQEN (N,N,N ',N '-tetrakis(2-quinolylmethyl) ethylenediamine) derivatives, T(MQ)EN(N,N,N ',N '-tetrakis(6-methoxy-2-quinolylmethyl)ethylenediamine) and T(TMQ)EN (N,N,N ',N '-tetrakis(5,6,7-trimethoxy-2-quinolylmethyl) ethylenediamine), have been prepared, and their fluorescence properties with respect to Zn2+ coordination were investigated. Introduction of a methoxy substituent at 6-position of the quinoline ring enhances the fluorescence intensity by 10-fold, and the three methoxy substituents in the 5,6,7-positions afford significant enhancement of the long-wavelength component of the fluorescence of zinc complex. The substituents did not alter the binding affinity of these compounds toward zinc ion significantly. T(MQ)EN was proved to be effective in detection of zinc ion in cells by fluorescent microscopy.
• Fluorescent zinc ion sensor
  申请人：Yano Shigenobu

  公开号：US20050182253A1

  公开（公告）日：2005-08-18

  A compound represented by the following general formula (I) or a salt thereof: wherein R 1 , R 2 , R 3 , and R 4 independently represent 2-quinolyl group which may be substituted, 1-isoquinolyl group which may be substituted, or 3-isoquinolyl group which may be substituted; m, n, p, and q independently represent 1 or 2; and L represents a single bond, or an alkylene group having 1 to 5 carbon atoms wherein said alkylene group may contain one or more heteroatoms in the main chain, and may have one or more substituents on the main chain, which is useful as a fluorescent zinc ion sensor.

  由以下一般式（I）表示的化合物或其盐：其中R1、R2、R3和R4分别表示可被取代的2-喹啉基团、可被取代的1-异喹啉基团或可被取代的3-异喹啉基团；m、n、p和q独立地表示1或2；L表示单键，或具有1至5个碳原子的烷基基团，其中该烷基基团可能在主链中含有一个或多个杂原子，并且可能在主链上具有一个或多个取代基，该化合物可用作荧光锌离子传感器。