2-[3-(2-(4-N-methyl-N-(2-hydroxyethyl)amino)phenyl)ethenyl-5,5-dimethylcyclohex-2-en-1-ylidene]-1,3-propanedinitrile

• 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: 2-[3-(2-(4-N-methyl-N-(2-hydroxyethyl)amino)phenyl)ethenyl-5,5-dimethylcyclohex-2-en-1-ylidene]-1,3-propanedinitrile
• 英文别名: 2-[3-((E)-2-{4-[(2-hydroxyethyl)(methyl)amino]phenyl}-1-ethenyl)-5,5-dimethyl-2-cyclohexenylidene]malononitrile；(E)-2-(3-(4-((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylcyclohex-2-en-1-ylidene)malononitrile；2-(3-(4E((2-hydroxyethyl)(methyl)amino)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile；2-[3-[(E)-2-[4-[2-hydroxyethyl(methyl)amino]phenyl]ethenyl]-5,5-dimethylcyclohex-2-en-1-ylidene]propanedinitrile
• 化学式: C₂₂H₂₅N₃O
• 分子量: 347.46
• InChiKey: GQCNTJWXSJJLEJ-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-降冰片烯-2-羧酸乙酯 、 2-[3-(2-(4-N-methyl-N-(2-hydroxyethyl)amino)phenyl)ethenyl-5,5-dimethylcyclohex-2-en-1-ylidene]-1,3-propanedinitrile 在 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以51%的产率得到Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-({4-[(E)-2-(3-dicyanomethylene-5,5-dimethyl-cyclohex-1-enyl)-vinyl]-phenyl}-methyl-amino)-ethyl ester
  参考文献：
  名称：

  Synthesis and Nonlinear-Optical Properties of Vinyl-Addition Poly(norbornene)s

  摘要：

  Vinyl-addition poly(norbornene) copolymers functionalized with nonlinear optical chromophore side groups have been prepared using (eta(6)-toluene)Ni(C6F5)(2), and their electrooptic properties have been characterized. The nickel complex used to polymerize the norbornene monomers is tolerant to many functional groups found in nonlinear optical chromophores although nitriles and amines other than trisubstituted amines strongly inhibit the reaction. A vinyl-addition copolymer of hexylnorbornene and a norbornene-functionalized Disperse Red 1 chromophore was scaled up and studied in detail. Initial studies indicate that electric field poling is effective but that relaxation of polar order in the poly(norbornene) is faster than in a comparable methacrylate copolymer.

  DOI：

  10.1021/ma040044i
• 作为产物：
  描述：

  异佛尔酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 50.0h， 生成 2-[3-(2-(4-N-methyl-N-(2-hydroxyethyl)amino)phenyl)ethenyl-5,5-dimethylcyclohex-2-en-1-ylidene]-1,3-propanedinitrile
  参考文献：
  名称：

  合理设计结晶诱导发射探针来检测活细胞中的无定形蛋白聚集

  摘要：

  与淀粉样蛋白聚集体不同，没有明确结构的无定形蛋白聚集体一直难以在复杂的细胞环境中靶向和检测。在这项研究中，我们合理地设计了来自聚集诱导发射探针（AIEgens）的无定形蛋白聚集传感器。利用二氰基异佛尔酮作为 AIEgen 支架模型，我们首先将 AIEgens 的荧光敏化到模拟无定形聚集蛋白内部的非极性和粘性环境。我们确定了一个普遍适用的部分（二甲氨基亚苯基）用于选择性结合和荧光增强。吸电子基团的调节调整了发射波长，同时保留了选择性检测。最后，我们利用优化的探针对蛋白质稳态网络调节下的聚集蛋白质组进行系统成像。总的来说，我们提出了一种合理的方法来开发 AIEgens 的无定形蛋白聚集传感器，具有可控的灵敏度、光谱覆盖范围和细胞性能。

  DOI：

  10.1002/anie.202103674

文献信息

• Influence of the chromophore ionization potential on speed and magnitude of photorefractive effects in poly(N-vinylcarbazole) based polymer composites
  作者：David Van Steenwinckel、Eric Hendrickx、André Persoons、Kurt Van den Broeck、Celest Samyn

  DOI：10.1063/1.481743

  日期：2000.6.22

  We report on the synthesis of three highly polar chromophores and their use as dopants in poly(N-vinylcarbazole) based photorefractive polymer composites sensitized with (2,4,7-trinitro-9-fluorenylidene)malononitrile. Small alterations in the amino donor group substituents were used to tune the dye’s ionization potential (IP) by 0.2 eV. At 780 nm, 5 °C above the glass transition temperature (Tg), and

  我们报告了三种高极性发色团的合成及其在聚 (N-乙烯基咔唑) 基光折变聚合物复合材料中用作掺杂剂的 (2,4,7-trinitro-9-fluorenylidene) 丙二腈。氨基供体基团取代基的微小变化用于将染料的电离电位 (IP) 调整 0.2 eV。在 780 nm，比玻璃化转变温度 (Tg) 高 5 °C，外加电场为 59 V/μm 时，我们观察到完全的内部衍射和 167 cm-1 的增益系数。在此温度范围内，发现衍射效率、增益系数和光折变相移与发色团 IP 相关。在低于 Tg 20 °C 时，双折射对折射率调制的贡献是微不足道的，并且光折变效应的速度与发色团 IP 密切相关。
• Synthesis and Nonlinear-Optical Properties of Vinyl-Addition Poly(norbornene)s
  作者：Ki Hong Park、Robert J. Twieg、R. Ravikiran、Larry F. Rhodes、Robert A. Shick、Diego Yankelevich、Andre Knoesen

  DOI：10.1021/ma040044i

  日期：2004.7.1

  Vinyl-addition poly(norbornene) copolymers functionalized with nonlinear optical chromophore side groups have been prepared using (eta(6)-toluene)Ni(C6F5)(2), and their electrooptic properties have been characterized. The nickel complex used to polymerize the norbornene monomers is tolerant to many functional groups found in nonlinear optical chromophores although nitriles and amines other than trisubstituted amines strongly inhibit the reaction. A vinyl-addition copolymer of hexylnorbornene and a norbornene-functionalized Disperse Red 1 chromophore was scaled up and studied in detail. Initial studies indicate that electric field poling is effective but that relaxation of polar order in the poly(norbornene) is faster than in a comparable methacrylate copolymer.
• Rational Design of Crystallization‐Induced‐Emission Probes To Detect Amorphous Protein Aggregation in Live Cells
  作者：Di Shen、Wenhan Jin、Yulong Bai、Yanan Huang、Haochen Lyu、Lianggang Zeng、Mengdie Wang、Yuqi Tang、Wang Wan、Xuepeng Dong、Zhenming Gao、Hai‐Long Piao、Xiaojing Liu、Yu Liu

  DOI：10.1002/anie.202103674

  日期：2021.7.12

  e) for selective binding and fluorescence enhancement. Regulation of the electron-withdrawing groups tuned the emission wavelength while retaining selective detection. Finally, we utilized the optimized probe to systematically image aggregated proteome upon proteostasis network regulation. Overall, we present a rational approach to develop amorphous protein aggregation sensors from AIEgens with controllable

  与淀粉样蛋白聚集体不同，没有明确结构的无定形蛋白聚集体一直难以在复杂的细胞环境中靶向和检测。在这项研究中，我们合理地设计了来自聚集诱导发射探针（AIEgens）的无定形蛋白聚集传感器。利用二氰基异佛尔酮作为 AIEgen 支架模型，我们首先将 AIEgens 的荧光敏化到模拟无定形聚集蛋白内部的非极性和粘性环境。我们确定了一个普遍适用的部分（二甲氨基亚苯基）用于选择性结合和荧光增强。吸电子基团的调节调整了发射波长，同时保留了选择性检测。最后，我们利用优化的探针对蛋白质稳态网络调节下的聚集蛋白质组进行系统成像。总的来说，我们提出了一种合理的方法来开发 AIEgens 的无定形蛋白聚集传感器，具有可控的灵敏度、光谱覆盖范围和细胞性能。