1(p-dimethylamino)phenyl-2-hydroxycyclobutene-3,4-dione | 107885-39-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1(p-dimethylamino)phenyl-2-hydroxycyclobutene-3,4-dione
• 英文别名: 3-(4-(dimethylamino)phenyl)-4-hydroxycyclobut-3-ene-1,2-dione；3-(4-(N,N-dimethylamino)phenyl)-4-hydroxycyclobut-3-ene-1,2-dione；3-Cyclobutene-1,2-dione, 3-[4-(dimethylamino)phenyl]-4-hydroxy-；3-[4-(dimethylamino)phenyl]-4-hydroxycyclobut-3-ene-1,2-dione
• CAS: 107885-39-2
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: GQZMKLRNTKUGHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1(p-dimethylamino)phenyl-2-hydroxycyclobutene-3,4-dione 、 3-羟基-N,N-二甲基苯胺 在 原甲酸三正丁基酯 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 3.0h， 以52%的产率得到bis<4-(dimethylamino)-2-hydroxyphenyl>squaraine
  参考文献：
  名称：

  Law, Kock-Yee; Bailey, F. Court, Canadian Journal of Chemistry, 1993, vol. 71, # 4, p. 494 - 505

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基苯胺 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.19h， 生成 1(p-dimethylamino)phenyl-2-hydroxycyclobutene-3,4-dione
  参考文献：
  名称：

  Squaric Acids:  A New Motif for Designing Inhibitors of Protein Tyrosine Phosphatases

  摘要：

  Protein tyrosine phosphatases (PTPases) are important targets in medicinal chemistry. These enzymes play a role in a number of human diseases, including type 11 diabetes and infection by Yersinia pestis, the causative agent of bubonic plague. Derivatives of squaric acids such as 2-aryl-1-hydroxycyclobut-1-ene-3,4-diones represent a new class of monoanionic inhibitors for PTPases.

  DOI：

  10.1021/ol036121w

文献信息

• Novel glycoconjugated squaraine dyes for selective optical imaging of cancer cells
  作者：M. Shimi、Vandana Sankar、M. K. Abdul Rahim、P. R. Nitha、Suresh Das、K. V. Radhakrishnan、K. G. Raghu

  DOI：10.1039/c6cc10282d

  日期：——

  Novel glycoconjugated squaraine dyes were synthesized, which exhibited excellent internalization in tumor cells and are potent fluorogenic imaging probes for tumor selective optical imaging.

  合成了新型糖缀合的方酸染料，其在肿瘤细胞中表现出优异的内在化，并且是用于肿瘤选择性光学成像的强力荧光成像探针。
• Highly selective and sensitive colourimetric detection of Hg2+ ions by unsymmetrical squaraine dyes
  作者：K.M. Shafeekh、M.K.A. Rahim、M.C. Basheer、C.H. Suresh、S. Das

  DOI：10.1016/j.dyepig.2012.11.013

  日期：2013.3

  A novel class of sulphonate group containing unsymmetrical squaraine dyes has been synthesized. These dyes show a selective and sensitive affinity towards Hg2+ in methanol and are practically insensitive to most other environmentally and biologically relevant metal ions. Isothermal titration calorimetric (ITC) studies and High Resolution Mass Spectral (HRMS) analysis indicate a 1:1 binding mode. 1H

  合成了一类新型的含磺酸盐基团的不对称方酸染料。这些染料对甲醇中的Hg 2+具有选择性和敏感的亲和力，并且实际上对大多数其他与环境和生物学相关的金属离子不敏感。等温滴定量热（ITC）研究和高分辨率质谱（HRMS）分析表明1：1结合模式。分离出的Dye…Hg 2+加合物的1 H和13 C NMR显示，Hg 2+沿着苯基-方形碳-碳键发生不寻常的加成反应，这也得到使用PM6能级几何结构的TD-DFT计算的支持。
• 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。
• Aggregation of Surfactant Squaraine Dyes in Aqueous Solution and Microheterogeneous Media:  Correlation of Aggregation Behavior with Molecular Structure
  作者：Huijuan Chen、Mohammad S. Farahat、Kock-Yee Law、David G. Whitten

  DOI：10.1021/ja9523911

  日期：1996.1.1

  several different squaraines are found to give spectrally blue-shifted aggregates in aqueous and mixed aqueous-organic solution and in microheterogeneous media (bilayer vesicles). While in some cases an intermediate dimer can be detected in the monomer to aggregate conversion process, in others direct conversion of monomer to aggregate is observed. The aggregation number can be determined together with

  报道了几种两亲性方酸染料的合成及其聚集行为和光物理的研究。发现几种不同的方酸在水性和混合水性有机溶液以及微异质介质（双层囊泡）中产生光谱蓝移的聚集体。虽然在某些情况下可以在单体到聚集体的转化过程中检测到中间二聚体，但在其他情况下观察到单体直接转化为聚集体。聚集数可以与一些方酸在不同环境中的平衡常数和热力学参数一起确定。在一些情况下，聚合数被发现是大约。4. 当在手性宿主（或反离子）存在下产生聚集体（但不是二聚体或单体）时，发现强烈的诱导圆二色性信号表明聚集体是手性的。从这些结果和分子模拟表明，一些方酸的扩展单层...
• A new approach to symmetrical and unsymmetrical photoconductive squaraines
  作者：Kock-Yee Law、F. Court Bailey

  DOI：10.1039/c39910001156

  日期：——

  A new synthesis for symmetrical and unsymmetrical photoconductive squaraines, based on a (2 + 2) cycloaddition, reductive-alkylation and condensation reaction sequence, is described.

  描述了一种基于(2 + 2)环加成、还原-烷基化和缩合反应序列的新合成方法，用于对称和非对称光导方方土的合成。