methyl 6-[4-(4-cyanophenyl)phenoxy]hexanoate | 141702-39-8

• 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: methyl 6-[4-(4-cyanophenyl)phenoxy]hexanoate
• CAS: 141702-39-8
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: IHLBHBAJZLVAGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 6-[4-(4-cyanophenyl)phenoxy]hexanoate 在 氢氧化钾 、 sodium hydroxide 、 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  Solid phase synthesis of liquid crystalline oligopeptides

  摘要：

  通过固相肽合成（SPPS）制备基于侧链介晶取代的L-赖氨酸残基的结构明确的液晶寡肽。

  DOI：

  10.1039/cc9960000353
• 作为产物：
  描述：

  6-溴己酸 在 硫酸 、 potassium carbonate 作用下， 生成 methyl 6-[4-(4-cyanophenyl)phenoxy]hexanoate
  参考文献：
  名称：

  Solid phase synthesis of liquid crystalline oligopeptides

  摘要：

  通过固相肽合成（SPPS）制备基于侧链介晶取代的L-赖氨酸残基的结构明确的液晶寡肽。

  DOI：

  10.1039/cc9960000353

文献信息

• Monodisperse liquid crystalline peptides
  作者：Peter A. G. Cormack、Barry D. Moore、David C. Sherrington

  DOI：10.1039/a701084b

  日期：——

  Solid phase peptide synthesis (SPPS) has been used as a synthetic tool to prepare monodisperse mesogen–oligopeptide conjugates with novel molecular architectures. Building upon previous success in this area, we have extended our methodologies to include a mesogenically substituted l-glutamic acid residue, and incorporated this derivative, as well as the l-lysine derivative previously reported, into a variety of new structures. Some novel liquid crystalline materials have been discovered. Bothalpha;-helical and beta;-sheet secondary structures have been explored as alternative scaffolds for the pendant mesogenic groups. The helical systems show most promise in terms of their ease of synthesis and handling, but at the relatively lower levels of mesogenic substitution studied so far, compared to the previously reported homo-oligopeptide materials, mesophases are not observed. The beta;-sheet materials prepared are rather insoluble and too high melting to have any practical value as thermotropic materials without further manipulation of their structures.

  固相肽合成（SPPS）被用作一种合成工具，用于制备具有新型分子结构的单分散介源寡肽共轭物。在这一领域取得成功的基础上，我们将方法扩展到中源取代的 l-谷氨酸残基，并将这种衍生物以及之前报道过的 l-赖氨酸衍生物加入到各种新结构中。发现了一些新型液晶材料。我们探索了α-螺旋和β-片状二级结构，作为悬垂介原基团的替代支架。螺旋系统在易于合成和处理方面最有前途，但与以前报道的同寡肽材料相比，目前研究的介原取代水平相对较低，没有观察到介相。制备出的β-片状材料相当不溶解，熔点过高，如果不对其结构进行进一步处理，作为热致性材料将没有任何实用价值。
• Liquid-Crystalline Properties of Poly(propylene imine) Dendrimers Functionalized with Cyanobiphenyl Mesogens at the Periphery
  作者：Maurice W. P. L. Baars、Serge H. M. Söntjens、Hartmut M. Fischer、H. W. I. Peerlings、E. W. Meijer

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2456::aid-chem2456>3.0.co;2-l

  日期：1998.12.4

  Three generations poly(propylene imine) dendrimers with 4, 16, and 64 terminal amine groups have been functionalized with pentyloxycyanobiphenyl and decyloxycyanobiphenyl mesogens. The liquid-crystalline properties of these dendrimers have been studied in detail by differential scanning calorimetry, optical polarization microscopy, and X-ray diffraction. All the mesogenic dendrimers orient into a smectic A mesophase. Thermal properties are influenced to a large extent by the spacer length, showing g-->S-A-->I transitions for the dendritic mesogens with the pentyloxy spacers and K-->S-A -->I transitions for the ones with a decyloxy spacer. In the latter, the temperature range of the mesophase increases with dendrimer generation. Mesophase formation in the case of the pentyloxy series is more difficult compared with the corresponding decyloxy analogues, when the transition enthalpies and the kinetics of obtaining microscopic textures are considered. The effect of generation on mesophase formation cannot be clearly distinguished, although in the case of the fifth-generation dendrimer with a decyloxy spacer, microscopic textures could be obtained more easily, compared with the lower generations. X-ray diffraction measurements of oriented samples indicate that the cyanobiphenyl endgroups of both series orient into an antiparallel-overlapping interdigitated structure. The observed S-A-layer spacings are independent of the dendrimer generation for both spacer lengths, indicating that the dendritic backbone has to adopt a completely distorted conformation, even for the higher generations.
• Design and Synthesis of Novel Calamitic and Discotic Materials Based on the Photorefractive Carbazole Unit
  作者：M. Manickam、P. Iqbal、N. Spencer、P. R. Ashton、S. Kumar、K. J. Donovan、J. A. Preece

  DOI：10.1080/15421400903568054

  日期：2010.3.22

  The incorporation of photorefractive molecular units, such as carbazole, into anisotropic materials (liquid crystals) may offer many advantages over conventional electrical poling of photorefractive polymers. Thus, a series of symmetric 3,6-disubstituted carbazole derivatives with well-known biphenyl and triphenylene liquid-crystalline moieties was synthesized and characterized. These modifications were achieved by the esterification of bishydroxy carbazole derivatives with monoalkylated biphenyl carboxylic acids and alkylation of bisacylated bromo- derivatives of carbazole with monohydroxy pentaalkoxy triphenylene. The pure compounds are not liquid-crystalline, even when doped with trinitrofluorenone (TNF), unlike triphenylene/carbazole materials that we reported previously. These compounds, although not liquid-crystalline, may be of interest in the field of photorefractivity.