(+/-)-1-O-(4-cyanomethylphenyl)glycerol

• 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: (+/-)-1-O-(4-cyanomethylphenyl)glycerol
• 英文别名: 4-cyanomethylphenylglycerol；2-(4-(2,3-dihydroxypropoxy)phenyl)acetonitrile；p-(2,3-dihydroxypropoxy)-phenylacetonitrile；2-[4-(2,3-Dihydroxypropoxy)phenyl]acetonitrile
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: KJYYNSOVXCPTIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-1-O-(4-cyanomethylphenyl)glycerol 在 potassium tert-butylate 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 15.0h， 生成 2-(4-(2,3-dihydroxypropoxy)phenyl)-3-(4-((3,4,5-tris(decyloxy)benzyl)oxy)phenyl)acrylonitrile
  参考文献：
  名称：

  两亲性α-氰基二苯乙烯衍生物的自组装，AIEE和变色性质

  摘要：

  一系列的两亲性α的-由在一端和在所述相对端的极性甘油基的亲脂性和柔性的烷基链的α氰基均棒状芯的氰基均衍生物已经通过偏光显微镜合成和研究，DSC，X射线散射， SEM，紫外可见光谱和光致发光测量。这些化合物可以自组装成SmA的液晶相序列-Col hex / p 6 mm -Cub I /P米3¯ñ在整体状态下和在有机溶剂中的多刺激响应性有机凝胶。它们在溶液，液晶态和凝胶态下具有可逆的光响应特性。它们还显示出聚集诱导的增强发射（AIEE）特性，同时，它们具有出色的机械变色行为，并且在研磨-发烟过程中具有良好的荧光转换可逆性。

  DOI：

  10.1016/j.tet.2017.07.010
• 作为产物：
  描述：

  对羟基苯乙腈 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 11.0h， 生成 (+/-)-1-O-(4-cyanomethylphenyl)glycerol
  参考文献：
  名称：

  α-Cyanostilbene and fluorene based bolaamphiphiles: synthesis, self-assembly, and AIEE properties with potential as white-light emissive materials and light-emitting liquid crystal displays

  摘要：

  报道的球形两亲分子自组装成具有独特分子排列的三角蜂窝相，并展现出聚集诱导发光（AIEE）效应。它们作为白光发光二极管（WLED）和低功耗液晶显示器（LE-LCD）设备的潜力已初步展示。

  DOI：

  10.1039/d0tc04571c

文献信息

• Inhibition of Secreted Phospholipase A₂. 4-Glycerol Derivatives of 4,5-Dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4<i>H</i>-oxadiazol-5-one with Broad Activities
  作者：Mohamed Touaibia、Atimé Djimdé、Fei Cao、Eric Boilard、Sofiane Bezzine、Gérard Lambeau、Catherine Redeuilh、Aazdine Lamouri、France Massicot、François Chau、Chang-Zhi Dong、Françoise Heymans

  DOI：10.1021/jm060082n

  日期：2007.4.1

  Secreted phospholipases A(2) (sPLA(2)s) have been reported to play an important role in various inflammatory conditions and thus represent an attractive therapeutic target. Previous SAR studies from our laboratory have revealed certain important features of our recently discovered specific hGIIA sPLA(2) inhibitors, and we report here the synthesis and biological activities of glycerol-containing derivatives of our lead compound III (Figure 1). Efficient and selective synthesis methods have been developed to make glycerol trisubstituted by different groups on desired positions. In terms of biological activities, the best compounds (A3, A6, and A15) are more active than III (Figure 1), as potent as Me-Indoxam, an sPLA(2)s inhibitor of reference, against hGIIA, hGV, and hGX sPLA(2)s and at least 10 times less active toward the GIB enzymes in two in vitro assay systems. By synthesis of enantiopure (S)-A6, we demonstrated that no important improvement of the inhibitory potency could be achieved by this approach. Furthermore, the results show that the global lipophilicity is likely responsible for the anti-PLA(2) activity and two oxadiazolone moieties seem too big to be accommodated by the active site of the hGIIA enzyme.
• US4252809A
  申请人：——

  公开号：US4252809A

  公开（公告）日：1981-02-24
• US4335119A
  申请人：——

  公开号：US4335119A

  公开（公告）日：1982-06-15
• Self-assembly, AIEE and mechanochromic properties of amphiphilic α-cyanostilbene derivatives
  作者：Yanming Ren、Ruilin Zhang、Chao Yan、Tingyan Wang、Huifang Cheng、Xiaohong Cheng

  DOI：10.1016/j.tet.2017.07.010

  日期：2017.8

  Colhex/p6mm- CubI/Pm3¯n in the bulk states and multistimuli responsive organogels in organic solvents. They have reversible photoresponsive properties in solution, liquid crystalline state and gel state. They also show aggregation-induced enhanced emission (AIEE) property, meanwhile, they present excellent mechanochromic behavior and have a good reversibility of fluorescence conversion upon grinding-fuming

  一系列的两亲性α的-由在一端和在所述相对端的极性甘油基的亲脂性和柔性的烷基链的α氰基均棒状芯的氰基均衍生物已经通过偏光显微镜合成和研究，DSC，X射线散射， SEM，紫外可见光谱和光致发光测量。这些化合物可以自组装成SmA的液晶相序列-Col hex / p 6 mm -Cub I /P米3¯ñ在整体状态下和在有机溶剂中的多刺激响应性有机凝胶。它们在溶液，液晶态和凝胶态下具有可逆的光响应特性。它们还显示出聚集诱导的增强发射（AIEE）特性，同时，它们具有出色的机械变色行为，并且在研磨-发烟过程中具有良好的荧光转换可逆性。
• α-Cyanostilbene and fluorene based bolaamphiphiles: synthesis, self-assembly, and AIEE properties with potential as white-light emissive materials and light-emitting liquid crystal displays
  作者：Deling Zhang、Yuantao Liu、Hongfei Gao、Qing Chang、Xiaohong Cheng

  DOI：10.1039/d0tc04571c

  日期：——

  Reported bolaamphiphiles self-assembled into triangular honeycomb phases with unique molecular arrangements, and showed the AIEE effect. Their potentials as both WLED and LE-LCD devices have been initially demonstrated.

  报道的球形两亲分子自组装成具有独特分子排列的三角蜂窝相，并展现出聚集诱导发光（AIEE）效应。它们作为白光发光二极管（WLED）和低功耗液晶显示器（LE-LCD）设备的潜力已初步展示。