(4-n-octyloxyphenyl)acetonitrile | 60982-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-n-octyloxyphenyl)acetonitrile
• 英文别名: 4-octyloxybenzylcyanide；(p-Octoxyphenyl)acetonitril；2-(4-Octoxyphenyl)acetonitrile
• CAS: 60982-69-6
• 化学式: C₁₆H₂₃NO
• mdl: MFCD09923861
• 分子量: 245.365
• InChiKey: WOGHZGHMZBULSA-UHFFFAOYSA-N

物化性质

• 熔点：
  36-38 °C
• 沸点：
  372.4±17.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-n-octyloxyphenyl)acetonitrile 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以90%的产率得到4-(n-octyloxy)phenylacetamidoxime
  参考文献：
  名称：

  Inhibition of secretory phospholipase A2. 2-Synthesis and structure–activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme

  摘要：

  We have recently reported the discovery of a series of specific inhibitors of human group IIA phospholipase A(2) (hGIIA PLA(2)) to display promising in vitro and in vivo properties. Here we describe the influence of different structural modifications on the specificity and potency against hGIIA PLA(2) versus porcine group IB PLA(2). The SAR results, as well as the log P and pK(a) values of oxadiazolone determined in this work, provide important information towards the comprehension of the mode of action of this kind of compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.016
• 作为产物：
  描述：

  溴代十四烷 、 对羟基苯乙腈 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到(4-n-octyloxyphenyl)acetonitrile
  参考文献：
  名称：

  Inhibition of secretory phospholipase A2. 2-Synthesis and structure–activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme

  摘要：

  We have recently reported the discovery of a series of specific inhibitors of human group IIA phospholipase A(2) (hGIIA PLA(2)) to display promising in vitro and in vivo properties. Here we describe the influence of different structural modifications on the specificity and potency against hGIIA PLA(2) versus porcine group IB PLA(2). The SAR results, as well as the log P and pK(a) values of oxadiazolone determined in this work, provide important information towards the comprehension of the mode of action of this kind of compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.016

文献信息

• Structural Engineering of Luminogens with High Emission Efficiency Both in Solution and in the Solid State
  作者：Hongwei Wu、Zhao Chen、Weijie Chi、Anivind Kaur Bindra、Long Gu、Cheng Qian、Bing Wu、Bingbing Yue、Guofeng Liu、Guangbao Yang、Liangliang Zhu、Yanli Zhao

  DOI：10.1002/anie.201906507

  日期：2019.8.12

  molecules in the excited state, allowing strong emission in dilute solution (quantum yield up to 98.2 %). On the other hand, intermolecular interactions of two distorted cyanostilbene units restrict molecular vibration and rotation, and long alkyl chains reduce the quenching effect of the π–π stacking to the excimer, eventually leading to strong emission in the solid state (quantum yield up to 60.7 %)

  在溶液和固态中开发具有高发射效率的分子仍然是一个巨大的挑战，因为大多数有机发光剂要么是由于聚集引起的猝灭，要么是由于聚集引起的发射分子。通过将平面的和扭曲的结构与长烷基侧链结合在一起以实现DAπAD型发射器，克服了这一难题。线性二苯基-二乙炔核和电荷转移效应可确保这些分子在激发态下具有相当大的平面性，从而在稀溶液中具有强发射能力（量子产率高达98.2％）。另一方面，两个扭曲的氰基茂金属单元的分子间相互作用限制了分子的振动和旋转，长烷基链降低了π-π堆积对准分子的猝灭作用，
• Alkyl-Chain Bridged Acrylonitrile-Appended Anthracene Chromophore toward Mechanically-Induced Bathochromic Shift
  作者：Hiroki Tanikubo、Takumi Matsuo、Shotaro Hayashi

  DOI：10.1246/bcsj.20220322

  日期：2023.2.15

  Designing π-conjugated molecules for mechanochromism have attracted much attention. Here, we found an approach toward mechanofluorochromic dyes, which are composed of dimeric 9-(4-methoxyphenyl)acrylonitrile-appended anthracene units bridged by an alkyl chain. The molecule in an amorphous state showed a dramatic bathochromic shift (ΔλPL = 75 nm) after grinding while a crystalline state of the monomer

  设计用于机械致色的π-共轭分子引起了很多关注。在这里，我们找到了一种制备机械荧光变色染料的方法，该染料由烷基链桥接的二聚 9-(4-甲氧基苯基) 丙烯腈附加蒽单元组成。处于非晶态的分子在研磨后显示出显着的红移（Δλ PL = 75 nm），而单体基序的结晶态则显示出小的浅色移（Δλ PL = 2 - 20 nm）。
• Spatial Patterning of Fluorescent Liquid Crystal Ink Based on Inkjet Printing
  作者：Lei Zhang、Yongfeng Cui、Qi Wang、Huimin Zhou、Hao Wang、Yuzhan Li、Zhou Yang、Hui Cao、Dong Wang、Wanli He

  DOI：10.3390/molecules27175536

  日期：——

  Fluorescent cholesteric liquid crystal materials (FCLC) with aggregation-induced emission (AIE) properties can effectively solve the contradiction between aggregation-induced quenching (ACQ) and liquid crystal self-assembly when light-emitting materials are aggregated, and they have great application value in the fields of anti-counterfeit detection and information hiding. However, generating a visually appealing design, logo, or image in the application typically requires an intricate fabrication process, such as the use of prefabricated molds and photomasks, which greatly limits the practical application of FCLC materials. Herein is reported a new method for spatially patterned liquid crystal (LC) microdroplet arrays using drop-on-demand inkjet printing technology. Through rational composition design, a spatial array composed of different liquid crystal microdroplets was established, and the array contains two entirely distinct but intact patterns at the same time, which can be reversibly switched under the irradiation of UV and natural light. This study provides a new method for the integrated preparation of different component liquid crystal materials.

  具有聚集诱导发射（AIE）特性的荧光胆甾液晶材料（FCLC）能够有效解决发光材料聚集时聚集诱导淬灭（ACQ）与液晶自组装之间的矛盾，在防伪检测和信息隐藏等领域具有重要的应用价值。然而，在应用中生成具有视觉吸引力的设计、标识或图像通常需要复杂的制造过程，例如使用预制模具和光掩模，这极大地限制了 FCLC 材料的实际应用。本文报道了一种利用按需滴墨喷印技术制作空间图案化液晶（LC）微液滴阵列的新方法。通过合理的组成设计，建立了由不同液晶微滴组成的空间阵列，该阵列同时包含两种完全不同但完整的图案，在紫外光和自然光的照射下可进行可逆切换。这项研究为集成制备不同成分的液晶材料提供了一种新方法。
• The Influence of Positional Isomerism of Terminal Alkyl Chains on Mesomorphic and Photophysical Behavior of Unsymmetric α-cyanostilbene-based Tetracatenars
  作者：Tianzhi Gao、Yurun Liang、Nana Liu、Xiaorong Wen、Xiaotong Liu、Hongfei Gao、Yulong Xiao

  DOI：10.1007/s10895-023-03424-8

  日期：——

  α-cyanostilbene, which could induce stereoisomerism and restricted intermolecular rotation in the aggregated state. Different mechanochromism behaviors could be achieved due to the positional isomerism of terminal alkyl chains. Therefore, tuning the position of terminal alkyl chains could give rise to distinct changes in the molecular aggregate, which provides a scheme to build multifunctional materials with

  采用 Suzuki 偶联和 Knoevenagel 反应制备了两个系列的不对称 α-氰芪基四丁醛，一端包含三条十六烷基链，另一端包含一条不同长度的烷基链。这些具有末端三个十六烷基链的四聚体与氰基相邻是非中间离子，而具有一条烷基链的异构体，与氰基相邻，在烷基链伸长时显示从非中间离子转变为单方六方柱状液晶。这种转变可归因于与氰基相邻的三个十六烷基链减少了π共轭刚性核之间的相互作用，阻碍了中间相的形成。此外，弱 slovatochromism 意味着两个系列四柱体中的弱 ICT。由于α-氰芪的存在，这两个系列异构体都表现出不同的 AIE 特性，这可以诱导立体异构并限制聚集状态下的分子间旋转。由于末端烷基链的位置异构性，可以实现不同的机械变色行为。因此，调整末端烷基链的位置可能会导致分子聚集体发生明显的变化，这为构建具有不同潜力的多功能材料提供了一种方案。
• Impact of the phenyl on fluorescence properties of cyanostilbene modified tetraphenylethene compounds
  作者：Xiaoqin Yi、Xiaotong Liu、Yurun Liang、Tianzhi Gao、Xiuning Hu、Yulong Xiao

  DOI：10.1016/j.jssc.2024.124688

  日期：2024.6

  cyanostilbene-modified tetraphenylethene derivatives were constructed by Williamson etherification, Suzuki coupling and Knoevenagel condensation reactions. Both compounds exhibited aggregation-induced emission and strong solid-state fluorescence behaviors with extremely high fluorescence quantum yield due to the distorted molecular conformation. Strangely, the compound without additional phenyl spacer did not

  通过Williamson醚化、Suzuki偶联和Knoevenagel缩合反应构建了两种新型氰基芪改性四苯乙烯衍生物。由于分子构象的扭曲，两种化合物均表现出聚集诱导发射和强固态荧光行为，并且具有极高的荧光量子产率。奇怪的是，没有额外苯基间隔基的化合物没有表现出机械致变色行为，而具有额外苯基间隔基的化合物表现出明显的机械致变色行为，研磨后发射波长从 480 nm 红移至 503 nm。所报道的化合物之间的力致变色行为的明显差异可以归因于额外的苯基间隔基有利于通过外部机械力进行分子平坦化。该研究为构建具有聚集诱导发光行为和高固态荧光量子产率的力致变色材料提供了一种方法，并促进了其在可重写发光纸中的应用。