9-[2-(3-Cyano-2-dicyanomethylen-5,5-dimethyl-2,5-dihydrofuran-4-yl)vinyl]-2,3,6,7-tetrahydro-1h, 5h-pyrido[3,2,1-ij]quinoline | 821789-52-0

• 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: 9-[2-(3-Cyano-2-dicyanomethylen-5,5-dimethyl-2,5-dihydrofuran-4-yl)vinyl]-2,3,6,7-tetrahydro-1h, 5h-pyrido[3,2,1-ij]quinoline
• 英文别名: 2-[4-[2-(1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)ethenyl]-3-cyano-5,5-dimethylfuran-2-ylidene]propanedinitrile
• CAS: 821789-52-0
• 化学式: C₂₄H₂₂N₄O
• 分子量: 382.465
• InChiKey: YOYDFFJDEIJUOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-醛基久洛尼定 、 2-(3-氰基-4,5,5-三甲基呋喃-2(5H)-亚甲基)丙二腈 以 乙醇 、 氯仿 为溶剂， 以24%的产率得到9-[2-(3-Cyano-2-dicyanomethylen-5,5-dimethyl-2,5-dihydrofuran-4-yl)vinyl]-2,3,6,7-tetrahydro-1h, 5h-pyrido[3,2,1-ij]quinoline
  参考文献：
  名称：

  D–π–A solvatochromic charge transfer dyes containing a 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran acceptor

  摘要：

  The preparation and solvatochromic behavior of novel, intramolecular charge transfer dyes obtained by the condensation of 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran with 4-dimethylamino benzaldehyde and 9-formyljulolidine are described. The absorption and fluorescence emission spectra of the dyes were studied in solvents of differing polarity. The dyes exhibited positive solvatochromism and their solvatochromic properties are discussed with the aid of semiempirical calculations. The HOMO and LUMO values of the dyes were obtained using both cyclic voltammetry and theoretical calculations; the electrochemical results were in agreement with both observed values and theoretical calculations. pH molecular switching was achieved by modulation of intramolecular charge transfer by means of protonation/deprotonation in DMSO solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.07.012

文献信息

• Fluorophore compounds and their use in biological systems
  申请人：Moerner E. William

  公开号：US20070134737A1

  公开（公告）日：2007-06-14

  Fluorophore compounds and methods for their use are disclosed. The fluorophores contain a 2-dicyanomethylen-3-cyano-2,5-dihydrofuran (DCDHF) moiety and one or more donor groups conjugated to the 2-dicyanomethylen-3-cyano-2,5-dihydrofuran group. The donor groups can contain atoms with free electron pairs such as oxygen, sulfur, nitrogen, or phosphorous. The fluorophore compounds can be used to label and detect biological molecules and biological structures either in vivo or in vitro.

  荧光物质化合物及其使用方法已被披露。这些荧光物质包含一个2-二氰甲亚甲基-3-氰基-2,5-二氢呋喃（DCDHF）基团，以及一个或多个与2-二氰甲亚甲基-3-氰基-2,5-二氢呋喃基团共轭的给体基团。给体基团可以包含具有自由电子对的原子，如氧、硫、氮或磷。这些荧光物质化合物可用于标记和检测生物分子和生物结构，无论是在体内还是体外。
• FLUOROPHORE COMPOUNDS AND THEIR USE IN BIOLOGICAL SYSTEMS
  申请人：MOERNER E. William

  公开号：US20050009109A1

  公开（公告）日：2005-01-13

  Fluorophore compounds and methods for their use are disclosed. The fluorophores contain a 2-dicyanomethylen-3-cyano-2,5-dihydrofuran (DCDHF) moiety and one or more donor groups conjugated to the 2-dicyanomethylen-3-cyano-2,5-dihydrofuran group. The donor groups can contain atoms with free electron pairs such as oxygen, sulfur, nitrogen, or phosphorous. The fluorophore compounds can be used to label and detect biological molecules and biological structures either in vivo or in vitro.

  本发明公开了荧光物质化合物及其使用方法。该荧光物质包含2-二氰基甲烯基-3-氰基-2,5-二氢呋喃（DCDHF）基团和一个或多个与2-二氰基甲烯基-3-氰基-2,5-二氢呋喃基团共轭的给体基团。这些给体基团可以包含具有自由电子对的原子，如氧、硫、氮或磷。该荧光物质化合物可用于标记和检测生物分子和生物结构，无论是在体内还是体外。
• [EN] FLUOROPHORE COMPOUNDS AND THEIR USE IN BIOLOGICAL SYSTEMS<br/>[FR] COMPOSES DE FLUOROPHORE ET LEUR UTILISATION DANS DES SYSTEMES BIOLOGIQUES
  申请人：UNIV STANFORD

  公开号：WO2005005956A2

  公开（公告）日：2005-01-20

  [EN] Fluorophore compounds and methods for their use are disclosed. The fluorophores contain a 2-dicyanomethylen-3-cyano-2,5-dihydrofuran (DCDHF) moiety and one or more donor groups conjugated to the 2-dicyanomethylen-3-cyano-2,5-dihydrofuran group. The donor groups can contain atoms with free electron pairs such as oxygen, sulfur, nitrogen, or phosphorous. The fluorophore compounds can be used to label and detect biological molecules and biological structures either in vivo or in vitro.
  [FR] La présente invention concerne des composés de fluorophore et des procédés pour les utiliser. Ces fluorophores contiennent un groupe 2-dicyanométhylène-3-cyano-2,5-dihydrofurane (DCDHF) et un ou plusieurs groupes donneurs qui sont conjugués au groupe 2-dicyanométhylène-3-cyano-2,5-dihydrofurane. Les groupes donneurs peuvent contenir des atomes avec des paires d'électrons libres, tels que de l'oxygène, du soufre, de l'azote ou du phosphore. Les composés de fluorophore selon cette invention peuvent être utilisés pour marquer et détecter des molécules biologiques et des structures biologiques soit in vivo, soit in vitro.
• D–π–A solvatochromic charge transfer dyes containing a 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran acceptor
  作者：Sung-Hoon Kim、Sue-Yoen Lee、Seon-Yeong Gwon、Young-A. Son、Jin-Seok Bae

  DOI：10.1016/j.dyepig.2009.07.012

  日期：2010.2

  The preparation and solvatochromic behavior of novel, intramolecular charge transfer dyes obtained by the condensation of 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran with 4-dimethylamino benzaldehyde and 9-formyljulolidine are described. The absorption and fluorescence emission spectra of the dyes were studied in solvents of differing polarity. The dyes exhibited positive solvatochromism and their solvatochromic properties are discussed with the aid of semiempirical calculations. The HOMO and LUMO values of the dyes were obtained using both cyclic voltammetry and theoretical calculations; the electrochemical results were in agreement with both observed values and theoretical calculations. pH molecular switching was achieved by modulation of intramolecular charge transfer by means of protonation/deprotonation in DMSO solution. (C) 2009 Elsevier Ltd. All rights reserved.