6-(benzo[d][1,3]dioxol-5-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile | 876150-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-(benzo[d][1,3]dioxol-5-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile
• 英文别名: 6-benzo[1,3]dioxol-5-yl-2-oxo-4-piperidin-1-yl-2H-pyran-3-carbonitrile；2-Oxo-4-piperidino-6-(1,3-benzodioxole-5-yl)-2H-pyran-3-carbonitrile；6-(1,3-benzodioxol-5-yl)-2-oxo-4-piperidin-1-ylpyran-3-carbonitrile
• CAS: 876150-29-7
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: QXQSEIVTDHNJMC-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C
• 沸点：
  463.4±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(benzo[d][1,3]dioxol-5-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile 、 脱氧茴香偶姻 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到4'',4'''-dimethoxy-3,4-methylenedioxy5'-(piperidin-1-yl)-[1,1';2',1'';3',1''']quaterphenyl-4'-carbonitrile
  参考文献：
  名称：

  Vapor-Phase Processable Novel Nonplanar Donor−Acceptor Quateraryls for Blue OLEDs^#

  摘要：

  A novel series of thermally stable blue light emitting quateraryls with a piperidine-donor and a nitrile acceptor was prepared from a ketene-S,S-acetal under mild conditions without using an organometal catalyst. The performance of a blue quateraryl 6e was investigated by fabricating a multilayer OLED with a configuration of ITO/PEDOT:PSS (40 nm)/quateraryl (60 nm)/BCP (6 nm)/Alq(3) (20 nm)/LiF (0.5 nm)/Al (200 nm), which exhibited blue emission with a low turn on voltage of 4 V at a brightness of 0.22 cd/m(2).

  DOI：

  10.1021/ol8008182
• 作为产物：
  描述：

  哌啶 、 3-cyano-4-methylthio-6-(3,4-methylenedioxy)phenyl-2H-pyran-2-one 以 乙醇 为溶剂， 生成 6-(benzo[d][1,3]dioxol-5-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  高效的取代基依赖的拥塞吡啶和嘧啶的合成

  摘要：

  碱催化的环转化描述了各种拥挤的吡啶3a - h，6a，b，8a - n，10a - g和16a，b以及（嘧啶-4-基）乙腈13a - g的高效通用合成方法。适当官能2 ħ -吡喃-2-酮1A - H ^，5，7，和15由乙酸甲脒2A，乙脒盐酸盐2b中，小号-methylisothiourea图9a，吡唑-1-基甲脒9B，和芳脒盐酸盐12分别在粉末KOH的无水DMF的存在。

  DOI：

  10.1016/j.tet.2007.07.062

文献信息

• [EN] SUBSTITUTED FLUORANTHENE-7-CARBONITRILES AS FLUORESCENT DYES FOR CELL IMAGING APPLICATIONS<br/>[FR] FLUORANTHÈNE-7-CARBONITRILES SUBSTITUÉS UTILISÉS EN TANT QUE COLORANTS FLUORESCENTS POUR DES APPLICATIONS D'IMAGERIE CELLULAIRE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014147642A1

  公开（公告）日：2014-09-25

  The present invention relates to novel donor-acceptor fluoranthenes of the general formula I which can be used potentially in developing fluorescent probes, and a process of preparing said novel compounds. More particularly, the present invention relates to amine or alkoxy group as donor and nitrile group as an acceptor attached to the fluoranthene skeleton, processes for preparing the said compounds and their uses as fluorescent probes in chemical and biological sciences such as cell imaging applications, diagnostics, fluorescent tags and other useful applications. The compounds are prepared by reacting 2H-pyran-2-ones in isolated or rigid conformations with cyclic ketones containing methylene carbonyl moiety in the presence of a base in an organic solvent.

  本发明涉及一种新型供体-受体氟蒽化合物，其通式为I，可能用于开发荧光探针，并提供了制备这些新型化合物的方法。更具体地说，本发明涉及将胺或烷氧基作为供体，将腈基作为受体连接到氟蒽骨架上，制备这些化合物的方法，以及它们在化学和生物科学中作为荧光探针的用途，如细胞成像应用、诊断、荧光标记和其他有用的应用。这些化合物是通过在有机溶剂中在孤立或刚性构象下，将2H-吡喃-2-酮与含有亚甲基羰基团的环状酮在碱存在下反应而制备的。
• Acetyltrimethylsilane:  A Novel Reagent for the Transformation of 2<i>H</i>-Pyran-2-ones to Unsymmetrical Biaryls
  作者：Atul Goel、Deepti Verma、Manish Dixit、Resmi Raghunandan、P. R. Maulik

  DOI：10.1021/jo052085y

  日期：2006.1.1

  An expeditious synthesis of unsymmetrical biaryls functionalized with electron-withdrawing or -donating substituents is described and illustrated by carbanion-induced ring transformation of 2H-pyran-2-one using acetyltrimethylsilane (ATMS) as a novel reagent in good yield. The novelty of the reaction lies in the creation of an aromatic ring from 2H-pyran-2-ones via two-carbon insertion from ATMS used

  用吸电子或给电子取代基官能化的不对称联芳基的快速合成方法得到了描述和说明，方法是使用乙酰基三甲基硅烷（ATMS）以高收率，通过碳负离子诱导的2 H-吡喃-2-酮的环转化。该反应的新颖性在于通过由用作碳负离子源的ATMS插入两个碳原子，由2个H-吡喃-2-酮生成一个芳香环。
• Regioselective synthesis of functionalized naphtho[b]thiophenes through a ‘lactone methodology’
  作者：Manish Dixit、Atul Goel

  DOI：10.1016/j.tetlet.2006.03.081

  日期：2006.5

  Benzo[b]thiophene and its benzannulated derivatives are important classes of compounds due to their unique chemical properties and biosteric relationship with indole. In this letter, we report a convenient route for the synthesis of substituted naphtho[b]thiophenes through a ring transformation reaction of suitably functionalized 2H-pyran-2-ones with 6,7-dihydro-5H-benzothiophene-4-one, in good yields

  苯并[ b ]噻吩及其苯甲环化衍生物由于其独特的化学性质和与吲哚的生物立体关系而成为重要的化合物。在这封信中，我们报告了通过适当官能化的2 H-吡喃-2-酮与6,7-二氢-5 H-苯并噻吩-4-酮的环转化反应，合成取代的萘并[ b ]噻吩的简便方法，收益率很高。
• New Fluoranthene FLUN-550 as a Fluorescent Probe for Selective Staining and Quantification of Intracellular Lipid Droplets
  作者：Atul Goel、Ashutosh Sharma、Manoj Kathuria、Arindam Bhattacharjee、Ashwni Verma、Prabhat R. Mishra、Aamir Nazir、Kalyan Mitra

  DOI：10.1021/ol403470d

  日期：2014.2.7

  A new class of live cell permeant, nontoxic fluoranthene-based fluorescent probe (FLUN-550) having a high Stokes shift in aqueous medium has been discovered. It showed selective staining of lipid droplets (LDs, dynamic cytoplasmic organelles) at a low concentration without background noise in in vitro live cell imaging of 3T3-L1 preadipocytes, J774 macrophages, MCF7 breast cancer cells, and single-celled, parasitic protozoa Leishmania donovani promastigotes and in vivo nonparasitic soil nematode C. elegans.
• Guanidine and amidine mediated synthesis of bridgehead triazaphenalenes, pyrimidines and pyridines through domino reactions
  作者：Ramendra Pratap、Abhijeet Deb Roy、Shom Prakash Kushwaha、Atul Goel、Raja Roy、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2007.06.073

  日期：2007.8

  An efficient and concise synthesis of 8-amino-2,5-diaryl-1,9,9b-triazaphenalene-4-carboiiitriles has been delineated through two successive base catalyzed heteroaromatic annulations of 6-aryl-4-(piperidin-1-yl)-2H-pyran-2-one-3-cai-bonitriles by Quanidine hydrochloride in moderate yield. This reaction was further explored through the ring transformation of 4 with amidines and 11 to afford (2 6-dia ryl pyri mid i n-4-yl)acetonitriles and 6-aryl-4-(piperidine-1-yl)nicotinonitriles in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.