6-(naphthalen-2-yl)-2-oxo-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile | 454703-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(naphthalen-2-yl)-2-oxo-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile
• 英文别名: 6-Naphthalen-2-yl-2-oxo-4-pyrrolidin-1-ylpyran-3-carbonitrile
• CAS: 454703-37-8
• 化学式: C₂₀H₁₆N₂O₂
• 分子量: 316.359
• InChiKey: CPLHQGALTHRBMY-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C
• 沸点：
  483.4±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(naphthalen-2-yl)-2-oxo-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile 在 氢氧化钾 、 甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 4-naphthalen-2-yl-6-oxo-2-pyrrolidin-1-yl-7,8-dihydro-5H-naphthalene-1-carbonitrile
  参考文献：
  名称：

  Carbanion induced synthesis of annulated unsymmetrical biaryls through ring transformation of 2H-pyran-2-oneCentral Drug Research Institute communication no. 6207

  摘要：

  创新而便捷地一步合成非对称大环双芳酯（3、5 和 8）、二苯并[a,c]环庚烯（10）、3,4-二氢-2(1H)-萘酮（15）、四氢异喹啉（18）、二氢-1H-异硫代苯（20）、苯并[c]硫代苯（22）和 2,3-二氢-1-苯并[c]环庚烯（22）、本研究描述了通过碱-化学反应获得的四氢异喹啉 (18)、二氢-1H-异硫代苯 (20)、苯并[c]硫代苯 (22) 和 2,3-二氢-1-苯并噻吩 (24)。这些化合物是通过环烷酮（2,4,7）、苯并环戊酮（9）、环己二酮单酮（12）、4-哌啶酮（17）、四氢噻喃-4-酮（19）、硫代苯并二氢吡喃-4-酮（21）或四氢噻吩-3-酮（23）中的一个碳离子对适当官能化的 2H-吡喃-2-酮（1,6）进行碱催化环转化反应而得到的。

  DOI：

  10.1039/b203544h
• 作为产物：
  描述：

  2-萘乙酮 在 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 6-(naphthalen-2-yl)-2-oxo-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  A new class of teraryl-based AIEgen for highly selective imaging of intracellular lipid droplets and its detection in advanced-stage human cervical cancer tissues

  摘要：

  设计并合成了一类新的基于 D-π-A teraryl 的 AIEgen 6a，用于细胞内脂滴的选择性染色。

  DOI：

  10.1039/d3tb01764h

文献信息

• Base-promoted regioselective synthesis of 1,2,3,4-terahydroquinolines and quinolines from N-boc-3-piperidone
  作者：Shally、Ismail Althagafi、Divya Singhal、Rahul Panwar、Ranjay Shaw、Amr Elagamy、Ramendra Pratap

  DOI：10.1016/j.tet.2019.130695

  日期：2019.11

  delineated by base mediated ring transformation of 6-aryl-4-substituted-2H-pyran-2-one-3-carbonitriles by N-boc-3-piperidone followed by consecutive deprotection of Boc group under acidic conditions. This reaction involves 2 new bond formations namely C4a-C5 and C8a-C8 in order to create the nucleus. Various donor and acceptor functional groups like aryl, heteroaryl, nitrile, methylsulfanyl and secondary

  通过供体基团介导的6-芳基-4-取代-2 H-吡喃-2-一-3-甲腈的碱介导的环转化，已经描述了具有供体和受体基团的1,2,3,4-四氢喹啉的有效合成。boc-3-哌啶酮，然后在酸性条件下连续脱保护Boc基团。该反应涉及2个新的键形成，即C4a-C5和C8a-C8，以产生核。在1,2,3,4-四氢喹啉中安装了各种供体和受体官能团，如芳基，杂芳基，腈，甲基硫烷基和仲胺。我们扩展了使用2-氧代苯并[ h]合成稠合的1,2,3,4-四氢喹啉的方法。]色烯作为前体。此外，我们通过DDQ对1,2,3,4-四氢喹啉进行芳香化合成了稠合和分离的喹啉，收率很高。Boc保护的四氢异喹啉6t的单晶X射线分析表明，N-Boc和芳基之间存在空间位阻。
• Synthesis of bicyclic biaryls as glucose-6-phosphatase inhibitors
  作者：Farhanullah、Brajendra K Tripathi、Arvind K Srivastava、Vishnu Ji Ram

  DOI：10.1016/j.bmc.2003.12.028

  日期：2004.3

  3-dihydrobenzo[b]thiophene-4-carbonitriles (3a-e), 8-(1-naphthyl)-6-s-amino-isothiochroman-5-carbonitriles (6a-d), 4-(1-naphthyl)-2-s-aminobezocycloalkene-1-carbonitriles (6e-j), 8-naphthyl-6-s-amino-2-ethyl-1,2,3,4-tetrahydro-isoquinoline-5-carbonitrle (6k-n), 1-naphthyl-3-s-amino-10H-9-thia-phenantherene-4-carbonitriles (8a-e) and 1-(1-naphthyl)-3-s-amino-9,10-dihydrophenantherene-4-carbonitriles

  联芳基，7-萘-5-s-氨基-2,3-二氢苯并[b]噻吩-4-甲腈（3a-e），8-（1-萘基）-6-s-氨基-异硫代苯并-5-甲腈（6a-d），4-（1-萘基）-2-s-氨基苯并环烯-1-腈（6e-j），8-萘基-6-s-氨基-2-乙基-1,2,3,4 -四氢-异喹啉-5-腈（6k-n），1-萘-3-s-氨基-10H-9-噻吩菲并-4-腈（8a-e）和1-（1-萘基）-3通过6-萘基-3-氰基-4-s-氨基-2H-吡喃-2-酮的碳负离子诱导的环转化反应制备了-s-氨基-9,10-二氢菲蒽-4-腈（8f-i） （1）来自相应的酮（2、5和7）。已经评估了这些化合物的葡萄糖-6磷酸酶抑制活性，并且仅6a，c，j，m，c，d，h显示出对葡萄糖-6磷酸酶的显着抑制。
• Carbanion induced, base-catalyzed, synthesis of highly functionalized 8-aryl-3,4-dihydro-2(1H)-naphthalenones from 2H-pyran-2-ones
  作者：Vishnu Ji Ram、Nidhi Agarwal、Farhanullah

  DOI：10.1016/s0040-4039(02)00528-2

  日期：2002.4

  A general and efficient synthesis of 8-aryl-5-methoxycarbonyl-6-methylsulfanyl-3,4-dihydro-2(1H)-naphthalenones 4a–i and 8-aryl-5-cyano-6-sec-amino-3,4-dihydro-2(1H)-naphthalenones 4l–r has been delineated from the acid hydrolysis of 8-aryl-5-methoxycarbonyl-6-methylsulfanyl-3,4-dihydro-2(1H)-naphthalenone-(2,2-dimethyltrimethylene)ketals 3a–i and 8-aryl-5-cyano-6-sec-amino-3,4-dihydro-2(1H)-naphthalenone-(2

  一般有效的合成8-芳基-5-甲氧基羰基-6-甲基硫烷基-3,4-二氢-2（1 H）-萘烯酮4a - i和8-芳基-5-氰基-6-仲-氨基-3 -1,4-二氢-2（1个H ^）-naphthalenones 4升- - [R已从的酸水解划定8芳基-5-甲氧基羰基-6-甲硫基-3,4-二氢-2（1 H ^）-naphthalenone-（ 2,2-二甲基三亚甲基缩酮3a - i和8-芳基-5-氰基6-仲-氨基-3,4-二氢-2（1 H）-萘酮-（2,2-二甲基三亚甲基）缩酮3l - r，由6-芳基-3-甲氧基羰基-4-甲基硫烷基-2 H-吡喃-2-酮1a – i和3-氰基-6-芳基-4-仲-氨基-2 H-吡喃-2的反应获得-酮类1升- - [R与1,4-环己二酮单- （2,2-二甲基亚丙基）缩酮2。
• 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.
• Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2<i>H</i>-Pyran-2-ones
  作者：Farhanullah、Nidhi Agarwal、Atul Goel、Vishnu Ji Ram

  DOI：10.1021/jo0204496

  日期：2003.4.1

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.