3-氯-4-[4-(二甲氨基)苯基]环丁-3-烯-1,2-二酮 | 107885-40-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-氯-4-[4-(二甲氨基)苯基]环丁-3-烯-1,2-二酮
• 英文名称: 3-Chloro-4-(4-dimethylamino-phenyl)-cyclobut-3-ene-1,2-dione
• 英文别名: 3-Chloro-4-[4-(dimethylamino)phenyl]cyclobut-3-ene-1,2-dione
• CAS: 107885-40-5
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: ZLOQIQCKQDJFES-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C (decomp)
• 沸点：
  372.1±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯-4-[4-(二甲氨基)苯基]环丁-3-烯-1,2-二酮 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 4.0h， 生成 1(p-dimethylamino)phenyl-2-hydroxycyclobutene-3,4-dione
  参考文献：
  名称：

  The synthesis and 1O2 photosensitization of halogenated asymmetric aniline-based squaraines

  摘要：

  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。

  DOI：

  10.1039/c0nj00949k
• 作为产物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 N,N-二甲基苯胺 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 3-氯-4-[4-(二甲氨基)苯基]环丁-3-烯-1,2-二酮
  参考文献：
  名称：

  The synthesis and 1O2 photosensitization of halogenated asymmetric aniline-based squaraines

  摘要：

  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。

  DOI：

  10.1039/c0nj00949k

文献信息

• Controlling Crystal Structures and Multiple Thermo- and Vapochromic Behaviors of Benzimidazole-Based Squaraine Dyes by Molecular Design and Solvent Adjustment
  作者：Guomin Xia、Shen Shen、Xin-Ming Hu、Zhengjun Jiang、Kaikai Xu、Mingda Wang、Hongming Wang

  DOI：10.1002/chem.201801518

  日期：2018.9.6

  molecular conformations and packing modes. These assemblies exhibited distinct optical properties, and in particular, SQB⋅solvent assemblies showed multiple thermo‐ and vapochromic effects. Thus, the SQB assemblies are potential fluorescent sensors for organic solvent vapors. More importantly, favorable optical‐waveguide properties were observed in these SQ‐based microstructures.

  由于其低成本，灵活的分子设计和可调节的自组装性，有机微结构和纳米结构有望成为具有理想性能的微光子和纳米光子材料的有前途的候选者。在这些候选化合物中，由于其固态非荧光性质以及它们的光学行为随形态变化而变化，因此很少研究著名的方酸染料（SQs）。在此贡献中，设计并在分子水平和通过溶剂调节设计和构造了两种新型的1,2-SQ，SQM和SQB，它们在结晶态下具有强的从黄色到红色的荧光发射。他们的自组装行为进行了研究，并透露，SQM组件提供一维微米棒，而1D微杆（ž -SQB ⋅ CH2氯2）和二维微板（ë -SQB ⋅ 2 CH 3 OH）可从SQB组件通过基于溶液的自组装方法获得的。这些SQ的不同组装行为归因于不同的π-π堆积相互作用，从而导致了不同的分子构象和堆积模式。这些组件表现出不同的光学特性，并且特别地，SQB ⋅溶剂组件呈多的热-和vapochromic效果。因此，SQB组件是用于有机溶
• Squaric Acids:  A New Motif for Designing Inhibitors of Protein Tyrosine Phosphatases
  作者：Jian Xie、Anthony B. Comeau、Christopher T. Seto

  DOI：10.1021/ol036121w

  日期：2004.1.1

  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.
• A Controlled Supramolecular Approach toward Cation-Specific Chemosensors:  Alkaline Earth Metal Ion-Driven Exciton Signaling in Squaraine Tethered Podands
  作者：Easwaran Arunkumar、Parayali Chithra、Ayyappanpillai Ajayaghosh

  DOI：10.1021/ja0393776

  日期：2004.6.1

  Three different squaraine tethered bichromophoric podands 3a-c with one, two, and three oxygen atoms in the podand chain and an analogous monochromophore 4a were synthesized and characterized. Among these, the bichromophores 3a-c showed high selectivity toward alkaline earth metal cations, particularly to Mg2+ and Ca2+ ions, whereas they were optically silent toward alkali metal ions. From the absorption and emission changes as well as from the Job plots, it is established that Mg2+ ions form 1:1 folded complexes with 3a and 3b whereas Ca2+ ions prefer to form 1:2 sandwich dimers. However, 3c invariably forms weak 1:1 complexes with Mg2+, Ca2+, and Sr2+ ions. The signal output in all of these cases was achieved by the formation of a sharp blue-shifted absorption and strong quenching of the emission of 3a-c. The signal transduction is achieved by the exciton interaction of the face-to-face stacked squaraine chromophores of the cation complex, which is a novel approach of specific cation sensing. The observed cation-induced changes in the optical properties are analogous to those of the "H" aggregates of squaraine dyes. Interestingly, a monochromophore 4a despite its binding, as evident from H-1 NMR studies, remained optically silent toward Mg2+ and Ca2+ ions. While the behavior of 4a toward Mg2+ ion is understood, its optical silence toward Ca2+ ion is rationalized to the preferential formation of a "Head-Tail-Tail-Head" arrangement in which exciton coupling is not possible. The present study is different from other known reports on chemosensors in the sense that cation-specific supramolecular host-guest complexation has been exploited for controlling chromophore interaction via cation-steered exciton coupling as the mode of signaling.
• AKASAKI, YUTAKA;TSUNEHDA, AKIXIKO;SAEHKI, SATORU;TORIGOEH, KAORU;IMAI, AK+
  作者：AKASAKI, YUTAKA、TSUNEHDA, AKIXIKO、SAEHKI, SATORU、TORIGOEH, KAORU、IMAI, AK+

  DOI：——

  日期：——
• AKASAKI, YUTAKA;TORIGOEH, KAORU;IMAI, AKIRA;TSUNEHDA, AKIXIKO;SAEHKI, CAT+
  作者：AKASAKI, YUTAKA、TORIGOEH, KAORU、IMAI, AKIRA、TSUNEHDA, AKIXIKO、SAEHKI, CAT+

  DOI：——

  日期：——