4-[4-(diethylamino)phenyl]-3-chlorocyclobut-3-ene-1,2-dione | 144630-65-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[4-(diethylamino)phenyl]-3-chlorocyclobut-3-ene-1,2-dione
• 英文别名: 3-[4-(diethylamino)phenyl]-4-chlorocyclobut-3-ene-1,2-dione；3-chloro-4-(4-(diethylamino)phenyl)cyclobut-3-ene-1,2-dione；3-Chloro-4-[4-(diethylamino)phenyl]cyclobut-3-ene-1,2-dione
• CAS: 144630-65-9
• 化学式: C₁₄H₁₄ClNO₂
• 分子量: 263.724
• InChiKey: ZZVFMOIBPJAHGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4-(diethylamino)phenyl]-3-chlorocyclobut-3-ene-1,2-dione 在 氢碘酸 、 溶剂黄146 作用下， 以 正丁醇 、 苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of Near-Infrared Absorbing Bisquarylium Dyes Bearing Unsymmetrically Extended π-Conjugation Structures

  摘要：

  新型阳离子双菁染料3和4是通过苯并噻唑基菁染料2与一系列4-取代的3-羟基或3-乙氧基环丁-3-烯-1,2-二酮反应制备的。这些染料在近红外区域显示出大且强烈的吸收，吸收峰位置在771至815纳米范围内变化。

  DOI：

  10.1055/s-2002-20034
• 作为产物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 N,N-二乙基苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以73%的产率得到4-[4-(diethylamino)phenyl]-3-chlorocyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Synthesis of bisquaraine dyes. Novel homologues of 1,2-squaraines bearing symmetrical and unsymmetrical structures

  摘要：

  为了研究1,2-方酸菁染料的类似结构，制备了两种新型同系物——双方酸菁1和2。通过对4,4'-双(3-异丙氧基环丁-3-烯-1,2-二酮)3与一系列杂环化合物5的反应，得到了在双方酸骨架的3和3'位置引入相同杂环组分的对称双方酸菁染料1。通过X射线结构分析证实了其中一种对称染料的结构，显示整个分子中存在一个延伸的π-共轭体系。非对称染料2的合成通过5与3'-单取代双方酸酯6的反应实现，该染料中引入了不同的芳香组分。每种双方酸菁染料均呈现出两个吸收峰，波长间隔为56-75 nm，其中较低能量的吸收峰位于653-757 nm。

  DOI：

  10.1039/b104059f

文献信息

• The synthesis and 1O2 photosensitization of halogenated asymmetric aniline-based squaraines
  作者：Chao Luo、Qianxiong Zhou、Guoyu Jiang、Liqing He、Baowen Zhang、Xuesong Wang

  DOI：10.1039/c0nj00949k

  日期：——

  The halogenated (brominated or iodinated) squaraines have promising potential in the application of photodynamic therapy (PDT). Though aniline-based squaraines are the most classical squaraine dyes, no halogenated derivatives with the halogen atoms directly incorporated in the conjugation skeleton of the squaraine chromophore have been reported so far. In this work, a stepwise synthetic approach, i.e. by way of the halogenated semi-squaraines, was applied successfully to prepare halogenated asymmetric aniline-based squaraines. Such a structure makes iodine atoms be able to exert significant heavy atom effect on the intersystem crossing (ISC) efficiency of the squaraine dye. As a result, the iodinated asymmetric squaraine (SQ–OH–I) exhibits a singlet oxygen (1O2) quantum yield as high as 0.54. In contrast, the 1O2 quantum yield of the non-halogenated squaraine analogue (SQ–OH) is only 0.02.

  溴化或碘化的方形染料在光动力治疗（PDT）应用中具有良好的潜力。尽管基于苯胺的方形染料是最经典的方形染料，但迄今为止尚未报道将卤素原子直接引入方形染料共轭骨架的卤素衍生物。在本研究中，成功应用了一种逐步合成的方法，即通过卤化半方形染料制备卤化不对称基于苯胺的方形染料。这种结构使碘原子能够对方形染料的系间交叉（ISC）效率施加显著的重原子效应。因此，碘化不对称方形染料（SQ–OH–I）的单重氧（1O2）量子产率高达0.54。相比之下，未卤化方形染料 аналог（SQ–OH）的1O2量子产率仅为0.02。
• Synthesis of bisquaraine dyes. Novel homologues of 1,2-squaraines bearing symmetrical and unsymmetrical structures
  作者：Yutaka Hyodo、Hiroyuki Nakazumi、Shigeyuki Yagi、Kazuhisa Nakai

  DOI：10.1039/b104059f

  日期：2001.11.1

  In order to investigate analogous structures of 1,2-squaraine dyes, bisquaraines 1 and 2 are newly prepared as their novel homologues. Symmetrical bisquaraine dye 1, in which the same heterocyclic components are introduced at the 3 and 3′ positions of the bisquaryl skeleton, is obtained by reaction of 4,4′-bi(3-isopropoxycyclobut-3-ene-1,2-dione) 3 with a series of heterocyclic compounds 5. The structure of one of the symmetrical dyes is confirmed by X-ray structural analysis, showing a largely extended π-conjugation system over the whole molecule. The synthesis of unsymmetrical dyes 2, in which different aromatic components are introduced, is established by the reactions of 5 with 3′-monosubstituted bisquarates 6. Each bisquaraine dye exhibits two absorption maxima separated by 56–75 nm, the lower-energy absorption of which is observed at 653–757 nm.

  为了研究1,2-方酸菁染料的类似结构，制备了两种新型同系物——双方酸菁1和2。通过对4,4'-双(3-异丙氧基环丁-3-烯-1,2-二酮)3与一系列杂环化合物5的反应，得到了在双方酸骨架的3和3'位置引入相同杂环组分的对称双方酸菁染料1。通过X射线结构分析证实了其中一种对称染料的结构，显示整个分子中存在一个延伸的π-共轭体系。非对称染料2的合成通过5与3'-单取代双方酸酯6的反应实现，该染料中引入了不同的芳香组分。每种双方酸菁染料均呈现出两个吸收峰，波长间隔为56-75 nm，其中较低能量的吸收峰位于653-757 nm。
• Synthesis of Near-Infrared Absorbing Bisquarylium Dyes Bearing Unsymmetrically Extended π-Conjugation Structures
  作者：Shigeyuki Yagi、Kazuhisa Nakai、Yutaka Hyodo、Hiroyuki Nakazumi

  DOI：10.1055/s-2002-20034

  日期：——

  Novel cationic bisquarylium dyes 3 and 4 were prepared by the reaction of benzothiazolinosquarylium dye 2 with a series of 4-substituted 3-hydroxy or 3-ethoxycyclobut-3-ene-1,2-diones. These dyes exhibit large and intense absorptions in the near-infrared region with varying absorption maxima in the range of 771 to 815 nm.

  新型阳离子双菁染料3和4是通过苯并噻唑基菁染料2与一系列4-取代的3-羟基或3-乙氧基环丁-3-烯-1,2-二酮反应制备的。这些染料在近红外区域显示出大且强烈的吸收，吸收峰位置在771至815纳米范围内变化。
• Supramolecular assembly of a new squaraine and β-cyclodextrin for detection of thiol-containing amino acids in water
  作者：Chao Luo、Qianxiong Zhou、Wanhua Lei、Jianguang Wang、Baowen Zhang、Xuesong Wang

  DOI：10.1080/10610278.2011.603730

  日期：2011.9.1

  A new unsymmetrical aniline-based squaraine (SQ2) bearing binding unit of Hg2+ ion was designed and synthesised. SQ2 can form 1:2 inclusion complex with beta-cyclodextrin, and the resulting complex, which undergoes absorption and fluorescence bleaching upon binding Hg2+, can serve as a turn-on colorimetric or fluorescent chemosensor in organic solvent-free aqueous solution for thiol-containing amino acids with high selectivity and tunable measuring range.