3-(dicyanomethylene)-5,5-dimethyl-1-(4-dimethylamino-styryl) cyclohexene | 27334-26-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(dicyanomethylene)-5,5-dimethyl-1-(4-dimethylamino-styryl) cyclohexene
• 英文别名: 2-(3-{2-[4-(Dimethylamino)phenyl]vinyl}-5,5-dimethyl-2-cyclohexen-1-ylidene)malononitrile；2-[3-[2-[4-(dimethylamino)phenyl]ethenyl]-5,5-dimethylcyclohex-2-en-1-ylidene]propanedinitrile
• CAS: 27334-26-5
• 化学式: C₂₁H₂₃N₃
• mdl: MFCD00228059
• 分子量: 317.434
• InChiKey: PJQMYUHLAJJKJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异佛尔酮 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 3-(dicyanomethylene)-5,5-dimethyl-1-(4-dimethylamino-styryl) cyclohexene
  参考文献：
  名称：

  调节基于二氰基异佛尔酮的荧光团的供体，用 NIR 荧光检测人血清白蛋白

  摘要：

  由于真实血清和尿液中内源性物质的短波长荧光的干扰，迫切需要开发用于检测人血清白蛋白（HSA）的NIR荧光探针。然而，以前的大多数报告都位于短波长区域 (< 600 nm)。在这项工作中，一系列dicyanoisophorone的（DCO）为基础的荧光1 - 4与不同的捐助团体已设计和调查。已经对其光物理特性进行了系统研究。在这些探针中，有4 种表现出 NIR 发射，具有最高的荧光亮度和对 HSA 最敏感的信号响应。进一步的研究表明，4可以以 1:1 的比例强力结合到 HSA 的 DS1 口袋中。重要的是，基于4的方法已被证明能够检测真实血清和尿液样本中的 HSA。

  DOI：

  10.1016/j.saa.2021.120666

文献信息

• Azetidine-Containing Heterospirocycles Enhance the Performance of Fluorophores
  作者：Junliang Zhou、Xianfeng Lin、Xin Ji、Shuang Xu、Chang Liu、Xiaochun Dong、Weili Zhao

  DOI：10.1021/acs.orglett.0c01414

  日期：2020.6.5

  utilized in various fluorescence imaging techniques. However, many existing modification strategies could not balance the performance (such as brightness, photostability, water solubility, and permeability) of fluorophores. Herein we report a general strategy to enhance the performance of donor–acceptor-type fluorophores by introducing azetidine-containing heterospirocycles to the commonly used fluorophore

  荧光染料广泛用于各种荧光成像技术中。但是，许多现有的修饰策略无法平衡荧光团的性能（例如亮度，光稳定性，水溶性和渗透性）。本文中，我们报告了通过将含氮杂环丁烷的杂螺环引入常用的荧光支架中来增强供体-受体型荧光团性能的一般策略。事实证明，这种策略是开发高质量荧光团的一般方法。
• 荧光化合物、其制备方法及作为荧光探针的应用
  申请人：中国科学院大连化学物理研究所

  公开号：CN115340511A

  公开（公告）日：2022-11-15

  本申请公开了一种荧光化合物、其制备方法及作为荧光探针的应用。包括一类以异氟尔酮为骨架的聚集诱导发光荧光分子。该类化合物在蛋白质维持完整三维结构时不发出荧光；当蛋白质错误折叠、变性并聚集时，分子可通过非共价键选择性高效结合，并在结合之后发出强烈荧光。所述荧光化合物的上述性质可通过非共价键识别探测活细胞内的聚集态蛋白质，且可用于活细胞原位荧光探测胞内蛋白质的聚集过程，为活细胞内原位探测聚集态蛋白质提供了便携、高效的方法。
• Synthesis and fluorescence of dicyanoisophorone derivatives
  作者：Xu Zhang、Yi Chen

  DOI：10.1016/j.dyepig.2013.05.031

  日期：2013.12

  A class of dicyanoisophorone derivatives 1-5 with electron-donating groups has been prepared by a two-step condensation reaction. Fluorescence both in solution and in pure solid state are measured. It is found that dicyanoisophorone derivatives 1-5 exhibit fluorescence in both solution and pure solid state. An enhancement of fluorescence in solid state probably results from the aggregation-induced emission. It is also found that dicyanoisophorone derivatives 1-5 show large Stoke's shifts in solution as well as in pure solid state. The origin of fluorescence of dicyanoisophorone derivatives depends on the nature of substituents, with a strong push pull chromophores dicyanoisophorone system, red or orange solid-state fluorescence is obtained. (C) 2013 Elsevier Ltd. All rights reserved.
• Red fluorescence thin film based on a strong push–pull dicyanoisophorone system
  作者：Zheng Gao、Xu Zhang、Yi Chen

  DOI：10.1016/j.dyepig.2014.08.014

  日期：2015.2

  Dicyanoisophorone derivatives (1-3), which contain a strong push pull chromophores system, have beep prepared by a two-step condensation reaction, and their fluorescence in solution, polymeric thin film and pure solid state are measured. It is found that 1-3 exhibit no or weak fluorescence in both solution and pure solid state, but strong red fluorescence in polymeric thin film. Mechanism study implies that the enhanced fluorescence of 1-3 in polymeric thin film results from the restriction of intramolecular vibrational and rotational motions. In addition, it is also found that the polarity of polymeric matrix has influence over the fluorescence of dicyanoisophorone derivatives, using PMMA as polymeric matrix, a fluorescent thin film with a strong red emission is obtained. (C) 2014 Elsevier Ltd. All rights reserved.
• Modulating donor of dicyanoisophorone-based fluorophores to detect human serum albumin with NIR fluorescence
  作者：Bin Liu、Xiongfei Zhao、Mei Zhou、Chao Song、Conghui Zeng、Tianyi Qin、Mingyuan Zhang、Zhongyong Xu

  DOI：10.1016/j.saa.2021.120666

  日期：2022.3

  It is urgently needed to develop NIR-fluorescent probe for detection of human serum albumin (HSA) since the interference of short-wavelength-fluorescence from endogenous species in real serum and urine. However, most previous reports were located in the short-wavelength region (< 600 nm). In this work, a series of dicyanoisophorone (DCO)-based fluorophores 1-4 with different donor groups have been

  由于真实血清和尿液中内源性物质的短波长荧光的干扰，迫切需要开发用于检测人血清白蛋白（HSA）的NIR荧光探针。然而，以前的大多数报告都位于短波长区域 (< 600 nm)。在这项工作中，一系列dicyanoisophorone的（DCO）为基础的荧光1 - 4与不同的捐助团体已设计和调查。已经对其光物理特性进行了系统研究。在这些探针中，有4 种表现出 NIR 发射，具有最高的荧光亮度和对 HSA 最敏感的信号响应。进一步的研究表明，4可以以 1:1 的比例强力结合到 HSA 的 DS1 口袋中。重要的是，基于4的方法已被证明能够检测真实血清和尿液样本中的 HSA。