2-((pyridin-2-yl)methylamino)-3-chloronaphthalene-1,4-dione | 21217-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((pyridin-2-yl)methylamino)-3-chloronaphthalene-1,4-dione
• 英文别名: 2-Chloro-3-[(2-pyridinylmethyl)amino]naphthoquinone；2-chloro-3-(pyridin-2-ylmethylamino)naphthalene-1,4-dione
• CAS: 21217-58-3
• 化学式: C₁₆H₁₁ClN₂O₂
• 分子量: 298.729
• InChiKey: ORDDUIQQGCMMCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 2-((pyridin-2-yl)methylamino)-3-chloronaphthalene-1,4-dione 在 三乙胺 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Naphthoquinone based chemosensor 2-(2′-aminomethylpyridine)-3-chloro-1,4-naphthoquinone for metal ions: Single crystal X-ray structure, experimental and TD-DFT study

  摘要：

  Naphthoquinone based redox active chemosensor 1; 2-(2'-aminomethylpyridine)-3-chloro-1,4-naphthoquinone ligand has been synthesized and characterized. Chemosensor 1 crystallizes in monoclinic space group P2(1)/n. Molecules showed intramolecular N-H center dot center dot center dot O and N-H center dot center dot center dot N, intermolecular N-H center dot center dot center dot O, C-H center dot center dot center dot O and slipped pi-pi stacking interactions. Chemosensor 1 showed orange colored solution in methanol and specifically detects Cu2+ ions by deprotonation of N-H. The deprotonation of amino N-H can also be achieved by mild base viz. triethylamine and chemosensor 1 can be used to detect several metal ions for example Ni2+, Mn2+ etc. that could observed by naked eye. Color changes observed were monitored by UV-visible and fluorescence spectra. Chemosensor 1 could provide either bidentate or tridentate coordination sites to metal ions. Redox nature of chemosensor 1 was evaluated by cyclic voltammetry studies. Electronic transition wavelengths of chemosensor 1 ligand have been evaluated in methanol, water and triethylamine by TD-DFT studies and comparative studies were performed with experimental results. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.03.016
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 2-氨甲基吡啶 以 乙醇 为溶剂， 反应 6.0h， 以91%的产率得到2-((pyridin-2-yl)methylamino)-3-chloronaphthalene-1,4-dione
  参考文献：
  名称：

  鉴定2-（烷基氨基）-3-氯-1,4-萘醌中异常的C–Cl⋯π接触：N取代基对晶体堆积，荧光，氧化还原和抗菌性能的影响†

  摘要：

  2,3-二氯-1,4-萘醌与不同的伯胺的化学选择性反应可得到一系列衍生物，例如2-（烷基氨基）-3-氯-1,4-萘醌（1-6）和2-（苄基氨基）-1,4-萘醌（7），收率高。通过微量分析，标准光谱和热重分析法对所有化合物1–7进行了全面表征。1-4和7的超分子结构用单晶X-射线衍射研究了CuO，以测定存在于胺官能团上的取代基对固态分子缔合的影响。研究表明，引入各种胺N取代基会引起构象变化，显然改变了非共价相互作用的供体-受体位点的性质和数量，从而导致了多种晶体堆积模式。有趣的是，在2和4中引入2-（苄氨基）-和2-（2-吡啶基甲基氨基）-取代基成功地打开了C–Cl⋯π合成子，这在有机分子的晶体堆积中几乎看不到。化合物1，2，4和5在350–620 nm范围内发出荧光，伴随的斯托克斯位移分别为81、131、141和131 nm，它们的循环伏安图证明了两个准可逆单电子波。所有化合物（5种除外）

  DOI：

  10.1039/c5ra02295a

文献信息

• 미세조류 파괴용 조성물
  申请人：Industry-Academic Cooperation Foundation, Chosun University 조선대학교산학협력단(220050171903) BRN ▼408-82-13419

  公开号：KR101761848B1

  公开（公告）日：2017-07-26

  본 발명은 미세조류 파괴용 조성물에 관한 것으로, 더욱 자세하게는 특정 치환기를 가지는 나프토퀴논 화합물을 함유하는 미세조류 파괴용 조성물에 관한 것이다. 본 발명에 따른 신규한 미세조류 파괴용 조성물은 해양 미세조류 배양장 또는 녹조 또는 적조가 발생된 지역 또는 녹조나 적조 발생 예상 지역에 처리하여 녹조 및 적조 피해를 예방할 수 있는 효과가 있다.

  本发明涉及微藻破坏用配方，更具体地涉及含有特定取代基的萘酮化合物的微藻破坏用配方。根据本发明，新型微藻破坏用配方可在海洋微藻培养场或发生褐藻或红藻的区域或预计发生褐藻或红藻的区域进行处理，以预防褐藻和红藻的损害。
• Identification of unusual C–Cl⋯π contacts in 2-(alkylamino)-3-chloro-1,4-naphthoquinones: effect of N-substituents on crystal packing, fluorescence, redox and anti-microbial properties
  作者：Vinay K. Singh、Sanjay K. Verma、Rahul Kadu、Shaikh M. Mobin

  DOI：10.1039/c5ra02295a

  日期：——

  N-substituents induces conformational changes that apparently modify the nature and number of donor–acceptor sites for noncovalent interactions, leading to diverse crystal packing patterns. Interestingly, the introduction of 2-(benzylamino)- and 2-(2-pyridylmethylamino)- substituents in 2 and 4 successfully switched on the C–Cl⋯π synthon, which is scarcely seen in the crystal packing of organic molecules

  2,3-二氯-1,4-萘醌与不同的伯胺的化学选择性反应可得到一系列衍生物，例如2-（烷基氨基）-3-氯-1,4-萘醌（1-6）和2-（苄基氨基）-1,4-萘醌（7），收率高。通过微量分析，标准光谱和热重分析法对所有化合物1–7进行了全面表征。1-4和7的超分子结构用单晶X-射线衍射研究了CuO，以测定存在于胺官能团上的取代基对固态分子缔合的影响。研究表明，引入各种胺N取代基会引起构象变化，显然改变了非共价相互作用的供体-受体位点的性质和数量，从而导致了多种晶体堆积模式。有趣的是，在2和4中引入2-（苄氨基）-和2-（2-吡啶基甲基氨基）-取代基成功地打开了C–Cl⋯π合成子，这在有机分子的晶体堆积中几乎看不到。化合物1，2，4和5在350–620 nm范围内发出荧光，伴随的斯托克斯位移分别为81、131、141和131 nm，它们的循环伏安图证明了两个准可逆单电子波。所有化合物（5种除外）
• Spectrophotometric and spectrofluorimetric studies on the selective sensing of fluoride ions by Co(II) and Ni(II) complexes of naphthoquinone derivative possessing enhanced H-bonding property
  作者：Selvaraj Madhupriya、Kuppanagounder P. Elango

  DOI：10.1016/j.saa.2012.06.020

  日期：2012.11

  [Ni(L)Cl2]·4H2O complexes, computed using fluorescent enhancement data, were found to be 0.6, 1.5 and 0.9 × 108 M−1, respectively, indicating enhancement of H-bond donor ability of the receptor unit, as a result of complexation with metal ions, towards fluoride ion sensing. Also, these sensors had high selectivity for fluoride ion detection over other common anions, such as Cl−, Br−, I−, AcO−, NO3−, H2PO4− and

  一种基于氨基萘醌（L）的新型比色化学传感器已被设计，合成和论证，该传感器带有直接与醌信号单元相连的NH受体单元。基于与受体单元的氢键形成，配体对氟离子表现出高度选择性的比色响应。利用荧光增强数据计算出的L及其正方形平面的[Co（L）Cl 2 ]·3H 2 O和[Ni（L）Cl 2 ]·4H 2 O络合物的结合常数为0.6、1.5和0.9×10 8  M -1分别表明，由于与金属离子络合，受体单元的H键供体能力增强了对氟离子的感应。此外，这些传感器对于有氟离子检测比其它普通阴离子，如Cl高选择性- ，溴- ，我-，ACO -，NO 3 -，H 2 PO 4 -和CN -的乙腈。
• Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur
  作者：Maicon Delarmelina、Renata D. Daltoé、Murilo F. Cerri、Klesia P. Madeira、Leticia B. A. Rangel、Valdemar Lacerda Júnior、Wanderson Romão、Alex G. Taranto、Sandro J. Greco

  DOI：10.5935/0103-5053.20150157

  日期：——

  Eleven 2,3-(substituted)-1,4-naphthoquinone derivatives were synthesized in yields ranging from 52-89%. These derivatives were evaluated for their cytotoxic effects on human lungs (H460), triple-negative breast (MDA-MB-231) and ovarian (A2780) cancer cell lines. Compounds 5f and 8 showed IC50 values of 3.048 x 10(-5) mol L-1 and 4.24 x 10(-6) mol L-1 for H460; 5c and 8 showed IC50 values of 2.16 x 10(-5) mol L-1 and 1.60 x 10(-5) mol L-1 for MDA-MB-231, and 5g and 8 showed IC50 values of 2.68 x 10(-6) mol L-1 and 3.89 x 10(-6) mol L-1 for A2780. Additionally, we conducted a docking study with the four most active compounds and the therapeutic targets PI3K and topoisomerase II showing the pharmacophoric conformation of these compounds.
• Highly selective colorimetric sensing of Cu(II) ions in aqueous solution via modulation of intramolecular charge transfer transition of aminonaphthoquinone chemosensor
  作者：Selvaraj Madhupriya、Kuppanagounder P. Elango

  DOI：10.1016/j.saa.2012.05.044

  日期：2012.11

  An aminonaphthoquinone based colorimetric chemosensor has been developed and demonstrated for the highly selective detection of Cu(II) ions in aqueous solution. The intramolecular charge transfer (ICT) transition exits in amine moiety directly attached to the quinone ring is modulated by the d-d transition of a square planar Cu(II)-receptor complex resulting in a change of color from yellow to blue. No significant color change was observed upon addition of other selected metal ions. The sensing property has been investigated using various spectral techniques (UV-Vis, fluorescence) and product analysis (Elemental analysis, magnetic moment, UV-Vis, FT-IR, EPR). (C) 2012 Elsevier By. All rights reserved.