4-(methylthio)-6-(4-nitrophenyl)-2-oxo-2H-pyran-3-carbonitrile | 251300-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(methylthio)-6-(4-nitrophenyl)-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 2H-Pyran-3-carbonitrile, 4-(methylthio)-6-(4-nitrophenyl)-2-oxo-；4-methylsulfanyl-6-(4-nitrophenyl)-2-oxopyran-3-carbonitrile
• CAS: 251300-66-0
• 化学式: C₁₃H₈N₂O₄S
• 分子量: 288.284
• InChiKey: HCXQILPGWICWKB-UHFFFAOYSA-N

物化性质

• 沸点：
  441.0±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

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：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(methylthio)-6-(4-nitrophenyl)-2-oxo-2H-pyran-3-carbonitrile 在 potassium hydroxide 、 肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-imino-6-oxo-10-(4-nitroyphenyl)-6,7,9,14-tetrahydro-13H-benzo[h]chromeno[4,3-d]pyrazolo[1,5-a]pyridine-12-carbonitrile
  参考文献：
  名称：

  A carbanion induced synthesis of highly congested pyrazole and imidazole containing heterocycles

  摘要：

  An efficient approach to the synthesis of highly congested di, penta and hexacyclic pyrazoles as well as imidazole fragment containing novel heterocyclic molecule has been developed through a carbanion induced transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans. Due to the presence of fluorescence, we report their prime application metal sensor as off/on switching in ferric ions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.095
• 作为产物：
  描述：

  2-氰-3,3-二(甲硫基)丙烯酸甲酯 、 对硝基苯乙酮 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 4-(methylthio)-6-(4-nitrophenyl)-2-oxo-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  高荧光吡唑和咪唑杂环的光物理和电化学研究

  摘要：

  研究了高度稠合的吡唑和咪唑环含杂环的光物理和电化学性质。在DMF介质中使用B3LYP / G（d，p）能级理论对分子进行TDDFT计算，结果与实验值吻合良好。咪唑衍生物显示出红移吸收峰（λ最大，455-474纳米）和较高的摩尔消光系数大于吡唑衍生物。在从吡唑到咪唑的π共轭增加的情况下，观察到发射最大值（537nm-565nm）中的红移。吸收和发射光谱的这些初步结果表明，这些分子可能具有有机应用的潜力。

  DOI：

  10.1016/j.dyepig.2016.09.030

文献信息

• Photophysical and electrochemical studies of highly fluorescent pyrazole and imidazole containing heterocycles
  作者：Hardesh K. Maurya、Ch. Pavan Kumar、M. Chandrasekharam、Atul Gupta

  DOI：10.1016/j.dyepig.2016.09.030

  日期：2017.1

  Highly congested pyrazole and imidazole ring containing heterocycles were studied for their photophysical and electrochemical properties. TDDFT calculations of the molecules were carried out using B3LYP/G(d,p) level theory in DMF medium and the results were in good agreement with the experimental values. The imidazole derivatives showed a red shifted absorption peak (λmax, 455–474 nm) and higher molar

  研究了高度稠合的吡唑和咪唑环含杂环的光物理和电化学性质。在DMF介质中使用B3LYP / G（d，p）能级理论对分子进行TDDFT计算，结果与实验值吻合良好。咪唑衍生物显示出红移吸收峰（λ最大，455-474纳米）和较高的摩尔消光系数大于吡唑衍生物。在从吡唑到咪唑的π共轭增加的情况下，观察到发射最大值（537nm-565nm）中的红移。吸收和发射光谱的这些初步结果表明，这些分子可能具有有机应用的潜力。
• One pot synthesis of tetrasubstituted thiophenes: [3 + 2] annulation strategy
  作者：Satya Narayan Sahu、Maneesh Kumar Gupta、Surjeet Singh、Pratik Yadav、Rahul Panwar、Abhinav Kumar、Vishnu Ji Ram、Brijesh Kumar、Ramendra Pratap

  DOI：10.1039/c5ra01290b

  日期：——

  A simple, efficient and economical synthesis of dimethyl 3-amino-5-(2-oxo-2-arylethyl)thiophene-2,4-dicarboxylates has been reported by ring opening of methyl 3-amino-6-aryl-4-oxo-4H-thieno[3,2-c]pyran-2-carboxylates by alkoxide ions.

  报道了一种简单、高效和经济的方法，通过烷氧根离子对甲基3-氨基-6-芳基-4-氧代-4H-噻吩[3,2-c]吡喃-2-羧酸酯进行环开启，合成了二甲基3-氨基-5-(2-氧代-2-芳基乙基)噻吩-2,4-二羧酸酯。
• An expeditious synthesis of imidazo[1,2-a]pyridines through nucleophile induced ring transformation reactions of 6-aryl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitriles
  作者：Vishnu Ji Ram、Nidhi Agarwal、Ashoke Sharon、Prakas R Maulik

  DOI：10.1016/s0040-4039(01)02112-8

  日期：2002.1

  An efficient and convenient synthesis of 2-(5-aryl-8-nitro-2,3-dihydroimidazo[1,2-a]pyridin-7(1H)-ylidene)acetonitriles (3) and 6-aryl-4-2-[(E)-nitromethylidene]-1-imidazolidinyl}-2-oxo-2H-pyran-3-carbonitriles (4) through nucleophile induced ring transformation of suitably functionalized 2H-pyran-2-one (1) from imidazoliden-2-ylidene nitromethane is delineated.

  有效和方便地合成2-（5-芳基-8-硝基-2,3-二氢咪唑并[1,2 - a ]吡啶-7（1 H）-亚烷基）乙腈（3）和6-芳基-4- 2-[（E）-硝基亚甲基] -1-咪唑啉基} -2-氧代-2 H-吡喃-3-甲腈（4）通过亲核试剂诱导的适当官能化的2 H-吡喃-2-酮的环转化（1）描绘了由咪唑啉-2-亚甲基硝基甲烷衍生的产物。
• A facile access to the synthesis of functionalised unsymmetrical biaryls from 2H-pyran-2-ones through carbanion induced C–C bond formation †
  作者：Vishnu J. Ram、Mahendra Nath、Pratibha Srivastava、Sanjay Sarkhel、Prakas R. Maulik

  DOI：10.1039/b005572g

  日期：——

  A convenient synthesis of highly functionalised biaryls 3 and 6 has been delineated through carbanion induced C–C bond formation from 6-aryl-3-cyano-4-substituted-2H-pyran-2-ones (1, 4) and acetone. Extension of this reaction, using aromatic ketones led to (4,6-diarylpyran-2-ylidene)acetonitrile (7) in lieu of the anticipated 2,4-diaryl-6-methylthiobenzonitrile (8). The structure of 2-methyl-6-methylthio-4-(3

  高度功能化的便捷合成 联芳基 3和6已经通过负碳离子诱导的C-C键形成划定由6-芳基-3-氰基-4-取代的-2- ħ -吡喃-2-酮（1，4），并丙酮。使用芳族化合物扩展该反应酮类导致（4,6-二芳基吡喃-2-亚甲基）乙腈（7）代替了预期的2,4-二芳基-6-甲基硫代苄腈（8）。的结构2-甲基-6-甲硫基-4-（3,4-亚甲基二氧苯基）苄腈（3f）由单晶X射线衍射 分析并显示出各种弱相互作用，这导致分子在结晶状态下的稳定性和堆积。
• Synthesis of Solution-Processable Donor–Acceptor Pyranone Dyads for White Organic Light-Emitting Devices
  作者：Chandra P. Sharma、Neeraj M. Gupta、Jagriti Singh、Rohit Ashok Kumar Yadav、Deepak Kumar Dubey、Kundan S. Rawat、Ajay K. Jha、Jwo-Huei Jou、Atul Goel

  DOI：10.1021/acs.joc.9b00293

  日期：2019.6.21

  A series of donor-acceptor pyranones (3a-m, 4a-h) were synthesized using alpha-oxo-ketene-S,S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five pyranones 3f, 3g, 3h, 3m, and 4e exhibited highly bright fluorescence in the solid state and weak or no emission in the solution state. Photophysical analysis of these dyes revealed that only 3f and 3m showed aggregation-induced emission behavior in a THF/water mixture (0-99%) with varying water fractions (f(w)) leading to bright fluorescence covering the entire visible region, while other derivatives 3g, 3h, and 4e did not show any fluorescence signal. The computational studies of the compounds revealed that the longer wavelength absorption originates from HOMO to LUMO electronic excitation. These dyes exhibited good thermal stability with 5% weight loss temperature in the range of 218-347 degrees C. The potential application of the donor-acceptor pyranone dyads was demonstrated by fabrication of solution-processed OLEDs. Remarkably, OLED devices prepared using highly emissive compounds 6-(anthracen-9-yl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile (3m) and 6-(4-methoxyphenyl)-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile (3f) displayed pure white emission with CIE coordinates of (0.29, 0.31) and (0.32, 0.32), respectively. Additionally, the resultant devices exhibited external quantum efficiencies of 1.9 and 1.2% at 100 cd m(-2), respectively.