4-hydroxy-4’-undecyloxybiphenyl | 501414-42-2

• 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-hydroxy-4’-undecyloxybiphenyl
• 英文别名: 4'-(undecyloxy)[1,1'-biphenyl]-4-ol；4-undecyloxy-4'-hydroxybiphenyl；4'-undecyloxy-biphenyl-4-ol；4,4'-undecyloxybiphenol；4-undecoxy-4'-biphenol；[1,1'-Biphenyl]-4-ol, 4'-(undecyloxy)-；4-(4-undecoxyphenyl)phenol
• CAS: 501414-42-2
• 化学式: C₂₃H₃₂O₂
• 分子量: 340.506
• InChiKey: WGRIWQCAXUQEPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4’-undecyloxybiphenyl 在 劳森试剂 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-((S)-sec-Butyl)-1-oxo-3-thioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid 4'-undecyloxy-biphenyl-4-yl ester
  参考文献：
  名称：

  Synthesis and liquid crystalline properties of monothio- and dithioimides with chiral N-substituents

  摘要：

  合成了两种化合物，即（S）-N-(2-甲基丁基)-4-[(4′-烯丙基氧基苯基-4-基)羟基苯乙酰亚胺]和（S）-N-(1-甲基丙基)-4-[(4′-烯丙基氧基苯基-4-基)羟基苯乙酰亚胺]，分别来自手性组分（S）-2-甲基丁醇和（S）-2-氨基丁烷。然后，将获得的酯亚胺用劳维森试剂处理，得到单硫和双硫亚胺。研究的所有亚胺和硫亚胺中都出现了液晶层状C*相。

  DOI：

  10.1039/b111391g
• 作为产物：
  描述：

  1-碘十一烷 、 4,4'-二羟基联苯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以68%的产率得到4-hydroxy-4’-undecyloxybiphenyl
  参考文献：
  名称：

  AN EFFICIENT, FACILE, AND FAST SYNTHESIS OF 4-ALKOXY-4′-HYDROXYBIPHENYLS

  摘要：

  A simple, fast and efficient method of synthesis of 4-alkoxy-4'-hydroxybiphenyls has been described. The reactions of 4,4'-dihydroxybiphenyl with appropriate alkyl halides were carried out over 3 h in DMSO in presence of solid powdered KOH.

  DOI：

  10.1081/scc-120014771

文献信息

• Nematic 2,5-disubstituted thiophenesElectronic supplementary information (ESI) available: extensive synthetic information. See http://www.rsc.org/suppdata/jm/b2/b202073b/
  作者：Neil L. Campbell、Warren L. Duffy、Gareth I. Thomas、Janine H. Wild、Stephen M. Kelly、Kevin Bartle、Mary O'Neill、Vicky Minter、Rachel P. Tuffin

  DOI：10.1039/b202073b

  日期：2002.8.30

  A large number of new liquid crystals incorporating the 2,5-disubstituted thiophene ring have been prepared and their mesomorphic behaviour studied in order to systematically investigate the correlation between the molecular structure and mesomorphism of thiophene derivatives with different shapes, polarisability and polarity. As a consequence of these investigations we have prepared a new class of liquid crystals incorporating a 2,5-disubstituted thiophene ring and a conjugated trans-carbon–carbon double bond in the terminal chain. These novel thiophene derivatives are the first liquid crystals incorporating a 2,5-disubstituted thiophene ring to exhibit a nematic phase at room temperature. This enables the flexoelectric coefficients of a bent-shaped molecule to be measured directly and at room temperature for the first time to the authors' knowledge. Many of these new thiophenes exhibit a high birefringence and a high nematic clearing point and are of potential use as components of nematic mixtures in LCDs.

  制备了大量含有2,5-二取代噻吩环的新型液晶，并研究了它们的介晶行为，以系统地探讨不同形状、极化能力和极性的噻吩衍生物的分子结构与介晶性之间的关联。通过这些研究，我们合成了一类新型液晶，它们含有2,5-二取代噻吩环和末端链中的共轭反式碳-碳双键。这些新颖的噻吩衍生物是首批在室温下表现出向列相的含有2,5-二取代噻吩环的液晶。这使得弯曲形状分子的挠曲电系数能够首次在作者所知的情况下直接在室温下测量。许多这些新型噻吩具有高双折射率和高向列相清亮点，有可能作为液晶显示器中向列相混合物的成分。
• Generation of biaxiality in smectic A phases by introduction of intermolecular perfluoroarene–arene and C–H/F interactions, and the non-odd–even effect of the molecules in their transition temperatures and layer distances
  作者：Keiki Kishikawa、Takahiro Inoue、Yoshiyuki Sasaki、Sumihiro Aikyo、Masahiro Takahashi、Shigeo Kohmoto

  DOI：10.1039/c1sm05887h

  日期：——

  Compounds 1a–j, 4-alkoxy-4′-pentafluorobenzoyloxybiphenyls, were synthesized to investigate the biaxiality in the smectic A phases of rod-like molecules possessing both perfluorinated and non-fluorinated benzene rings. The phase behaviors of the compounds and the molecular packing structures of their smectic A phases were investigated by polarized optical microscopy (POM), differential scanning colorimetry (DSC), and X-ray diffraction (XRD). As a result, it was found that the plot of the transition temperatures against the number of carbon atoms in the terminal alkyl chains did not show a clear odd–even effect, and an unique effect “tgg-effect” was observed in the plots of their layer distances against the number of carbon atoms. In the detailed 1D- and 2D-XRD studies of the smectic A phases, lateral directional orders in each layer were observed. It is assumed that these results originate from the biaxiality of the smectic A phases and slow rotation of the molecules around their molecular long axes.

  化合物1a–j，即4-烷氧基-4′-五氟苯甲酸氧基联苯，被合成用于研究具有全氟化和非氟化苯环的棒状分子在液晶A相中的双轴性。通过偏光显微镜（POM）、差示扫描量热法（DSC）和X射线衍射（XRD）研究了这些化合物的相行为及其液晶A相的分子排列结构。结果发现，过渡温度与末端烷基链中碳原子数的图示并未显示出明显的奇偶效应，而在层间距与碳原子数的图示中观察到一个独特的“tgg效应”。在液晶A相的详细一维和二维X射线衍射研究中，观察到每一层中的横向方向有序性。这些结果被认为是源于液晶A相的双轴性以及分子绕其长轴的缓慢旋转。
• Synthesis and Liquid Crystalline Properties of Novel Imides and Thioimides with Chiral Aliphatic Tails
  作者：Andrzej Orzeszko、Dorota Melon-Ksyta、Ewa Kowalczyk、Krzysztof Czupryński

  DOI：10.1515/znb-2003-1013

  日期：2003.10.1

  Three chiral compounds (R)-octan-2-ol, (S)-citronellol and (S)-citronellyl bromide were used for the synthesis of novel ester imides with biphenyl moieties as mesogenic units. Observations by means of polarising microscopy as well as DSC measurements revealed the presence of SmC* and/or SmA phases for all the compounds examined. It was found that the biphenyl units with long chiral alkoxy substituents induce smectic C phases.

  三种手性化合物(R)-辛醇，(S)-香茅醇和(S)-香茅溴化物被用于合成具有联苯基团作为介向单元的新型酯亚胺。通过偏光显微镜观察和DSC测量发现，所有检测的化合物均存在SmC*和/或SmA相。发现长手性烷氧基取代物的联苯基团诱导出蜡状C相。
• Ferroelectric-like behaviour of the SmCP phase in liquid crystalline compounds with asymmetrical bent-core molecules
  作者：V. Novotná、M. Kašpar、V. Hamplová、M. Glogarová、L. Lejček、J. Kroupa、D. Pociecha

  DOI：10.1039/b601084a

  日期：——

  A new series of asymmetrical bent-shaped mesogens has been synthesised and their mesomorphic properties studied. All compounds exhibit the B2 (SmCP) phase. For some compounds we found a very low coercive field for switching to the saturated ferroelectric state and only one peak in the switching current. Due to the lack of SHG signal in the zero field state and the behaviour of the relaxation mode we cannot unambiguously assign ferroelectric or antiferroelectric character to the B2 phase observed. The observation of planar samples revealed a striped texture. Large optically active domains appear on very slow cooling, which are attributed to a non-homogeneous (twisted) in-plane structure imposed by surfaces. The twisted domains are suppressed under a critical electric field. A simple model of such a structure and its behavior in the electric field is proposed. The low temperature phase detected on further cooling is attributed to a crystalline-like smectic phase.

  我们合成了一系列新的不对称弯曲状介质，并研究了它们的介质性质。所有化合物都呈现出 B2（SmCP）相。对于某些化合物，我们发现切换到饱和铁电态的矫顽力场非常低，而且切换电流只有一个峰值。由于在零磁场状态下缺乏 SHG 信号以及弛豫模式的行为，我们无法明确地为观察到的 B2 相赋予铁电或反铁电特性。对平面样品的观察显示出一种条状纹理。在非常缓慢的冷却过程中会出现大的光学活性畴，这归因于表面施加的非均质（扭曲）面内结构。在临界电场下，扭曲畴被抑制。本文提出了这种结构及其在电场中行为的简单模型。在进一步冷却时检测到的低温相归因于类似晶体的胶凝相。
• Novel ferrocene diesters with liquid-crystal properties
  作者：J. Bhatt、B. M. Fung、K. M. Nicholas、C.-D. Poon

  DOI：10.1039/c39880001439

  日期：——

  A series of bis-(4-alkoxy-4′-biphenyl)ferrocene 1,1′-diesters (1) has been synthesized; three compounds in this homologous series exhibit liquid-crystal phases.

  合成了一系列的双-（4-烷氧基-4'-联苯）二茂铁1,1'-二酯（1）；该同源系列中的三种化合物显示液晶相。