苯甲酸,4-羟基-,4-(十二烷氧基)苯基酯 | 148731-30-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 苯甲酸,4-羟基-,4-(十二烷氧基)苯基酯
• 英文名称: 4-(4-Dodecyloxyphenoxycarbonyl)phenol
• 英文别名: 4-dodecyloxyphenyl 4-hydroxybenzoate；4-(Dodecyloxy)phenyl 4-hydroxybenzoate；(4-dodecoxyphenyl) 4-hydroxybenzoate
• CAS: 148731-30-0
• 化学式: C₂₅H₃₄O₄
• 分子量: 398.543
• InChiKey: PERYDRPRBMWDOF-UHFFFAOYSA-N

物化性质

• 沸点：
  543.1±35.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酸,4-羟基-,4-(十二烷氧基)苯基酯 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-((3-(3-(4-((4-(dodecyloxy)phenoxy)carbonyl)phenoxy)-3-oxoprop-1-en-1-yl)phenoxy)carbonyl)phenyl 4-(dodecyloxy)benzoate
  参考文献：
  名称：

  3-羟基肉桂酸–弯曲型液晶设计的新中心核心†

  摘要：

  提出了一系列基于3-羟基肉桂酸的弯曲形液晶的合成和介晶性质。所制备的化合物在侧臂之一中的酯连接基团的取向上不同。另外，通过使用烷氧基或羧基端基和通过改变末端烷基链的长度来调节介晶性质。进行了纹理观察和量热研究，以及电光，X射线和介电测量。已经确定了酯连接基团取向和末端烷基链的长度对介晶行为的影响。在研究的12种化合物中，只有一个形成层状相，即B 2 –B 5相顺序，而所有其他相均显示柱状相，取决于酯基的方向，为B 1或B 1Rev类型。已使用X射线衍射技术对纯材料以及形成B 1和B 1Rev相的化合物的二元混合物进行了详细的研究，研究了柱状相的结构性质。关于分子结构讨论了所有结果。

  DOI：

  10.1039/c3tc30664j
• 作为产物：
  描述：

  苯甲酸,4-(苯基甲氧基)-,4-(十二烷氧基)苯基酯 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 苯甲酸,4-羟基-,4-(十二烷氧基)苯基酯
  参考文献：
  名称：

  1,1'-二取代二茂铁含结构的热致液晶的[Fe {（η 5 -C 5 H ^ 4）COOC 6 H ^ 4 XC 6 H ^ 4 OC Ñ ħ 2N + 1 } 2 ]（X OOC或COO）。中央酯官能团的取向对介晶性质的影响

  摘要：

  合成了在刚性有机部分中包括的酯功能的方向不同的1，1′-二取代的二茂铁的两个系列I和II，并且研究了它们的液晶性质。已发现后者很大程度上取决于连接酯基的取向和烷基链长。

  DOI：

  10.1002/hlca.19930760210

文献信息

• Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core
  作者：Anna Kovářová、Svatopluk Světlík、Václav Kozmík、Jiří Svoboda、Vladimíra Novotná、Damian Pociecha、Ewa Gorecka、Natalia Podoliak

  DOI：10.3762/bjoc.10.75

  日期：——

  Bent-shaped mesogens possessing a biphenyl as a central core have been synthesized and the role of the terminal chain and the orientation of the ester as a linkage group have been investigated. For the studied molecular core we have established that both parameters play an important role for the mesomorphic properties. The polyfluoroalkyl terminal chain supports the formation of mesophases, and the introduction of a chiral lactate terminal chain destabilizes mesophases for the first type of mutual orientation of ester groups, attached to the central core. On the contrary, for the opposite orientation of esters, the terminal chain has no effect on the mesomorphic properties, and columnar phases have been found for all compounds. A unique phase sequence has been found for the mesogen with the fluorinated chain. A generalized tilted smectics, SmC_G, have been observed in a temperature interval between two different lamellar SmCP phases and characterized by X-ray and dielectric measurements. The dielectric spectroscopy data are unique and presented for the first time in the SmC_G phase providing new information about the molecular dynamics.

  具有联苯作为中心核心的弯曲形态基团已被合成，并研究了末端链和酯作为连接基团的取向。针对所研究的分子核心，我们已经确定这两个参数对向列相性质起重要作用。多氟烷基末端链支持向列相的形成，而手性乳酸酯末端链的引入破坏了第一种酯基相互取向方式附着在中心核心上的向列相。相反，对于酯基的相反取向，末端链对向列相性质没有影响，并且所有化合物都发现了柱状相。对于具有氟化链的基团，发现了独特的相序列。在两种不同的层状SmCP相之间的温度区间内观察到了广义倾斜液晶相SmC_G，并通过X射线和介电测量进行了表征。介电谱数据是独特的，并首次在SmC_G相中提供了关于分子动力学的新信息。
• Ferroelectric and antiferroelectric switching behaviour in new unsymmetrical bent-core compounds derived from 3-hydroxybenzoic acid
  作者：H. N. Shreenivasa Murthy、B. K. Sadashiva

  DOI：10.1039/b419404g

  日期：——

  Herein we report the synthesis and characterization of several achiral bent-core unsymmetrical compounds exhibiting mesomorphic properties. The lower homologues in two series of compounds show a columnar phase with a rectangular lattice whereas the middle homologues exhibit a novel columnar phase with an oblique lattice. Interestingly, three of the higher homologues of the laterally unsubstituted compounds exhibit a smectic phase with ferroelectric switching characteristics and the analogous fluoro-substituted compounds show a smectic phase that is composed of antiferroelectric conglomerates.

  在此，我们报告了几种表现出介形特性的非手性弯曲核不对称化合物的合成和表征。两个系列化合物中的低级同系物显示出具有矩形晶格的柱状相，而中级同系物则显示出具有斜晶格的新型柱状相。有趣的是，横向未取代化合物的三个较高同系物显示出一种具有铁电开关特性的晶相，而类似的氟取代化合物则显示出一种由反铁电聚集体组成的晶相。
• 1,1?-Disubstituted Ferrocene-Containing Thermotropic Liquid Crystals of structure [Fe{(?5-C5H4)COOC6H4XC6H4OCnH2n+1}2] (X ? OOC or COO). Influence of the orientation of the central ester function on the mesogenic properties
  作者：Robert Deschenaux、Jean-Lue Marendaz、Julio Santiago

  DOI：10.1002/hlca.19930760210

  日期：1993.3.24

  The two series I and II of 1,1′ -disubstituted ferrocenes which differ by the direction of the ester function included in the rigid organic part were synthesized and their liquid crystal properties examined. These latter were found to be strongly dependent on the orientation of the connecting ester group and on the alkyl chain length.

  合成了在刚性有机部分中包括的酯功能的方向不同的1，1′-二取代的二茂铁的两个系列I和II，并且研究了它们的液晶性质。已发现后者很大程度上取决于连接酯基的取向和烷基链长。
• Ten isomeric five-ring bent-core mesogens: The influence of the direction of the carboxyl connecting groups on the mesophase behaviour
  作者：Wolfgang Weissflog、Gisela Naumann、Bedrich Kosata、Martin W. Schröder、Alexey Eremin、Siegmar Diele、Zinaida Vakhovskaya、Horst Kresse、Rudolf Friedemann、S. Ananda Rama Krishnan、Gerhard Pelzl

  DOI：10.1039/b508488a

  日期：——

  In order to study the role of the direction of the connecting groups in bent-core mesogens we synthesized two series of ten possible achiral isomeric five-ring bent-core compounds in which all aromatic rings are connected by ester groups and each of which possesses the same length of the terminal chains (octyloxy or dodecyloxy, respectively). The structure of the isomers is distinguished by the direction of at least one ester group, only. The mesophase behaviour of the compounds has been studied by polarizing microscopy, differential scanning calorimetry, X-ray experiments and electro-optical measurements. We have found that in spite of the minor structural differences a variety of mesophases occur (SmCPA, Colrec, Colob) whereby the clearing temperatures vary from 121 to 193 °C (octyloxy isomers) and 112 to 189 °C (dodecyloxy isomers). Depending on the direction of the ester groups some of these isomers show interesting properties, such as field-induced inversion of chirality in SmCPA and columnar phases, the field-induced enhancement of the clearing temperature, a second-order phase transition Colob → SmCPA or the reversible field-induced phase transition Colob → SmCPF. The unexpectedly strong influence of the direction of the connecting groups is discussed on the base of theoretical calculations and molecular dynamics simulation on isolated molecules.

  为了研究连接基团方向在弯核介素中的作用，我们合成了两个系列的十种可能的非手性异构五环弯核化合物，其中所有的芳香环都由酯基连接，每种化合物都具有相同长度的末端链（分别为辛氧基或十二氧基）。异构体的结构仅以至少一个酯基的方向来区分。我们通过偏光显微镜、差示扫描量热法、X 射线实验和电光测量等方法对这些化合物的介相行为进行了研究。我们发现，尽管结构上存在细微差别，但还是出现了多种介相（SmCPA、Colrec、Colob），其清除温度在 121 至 193 ℃（辛氧基异构体）和 112 至 189 ℃（十二烷氧基异构体）之间变化。根据酯基方向的不同，其中一些异构体显示出有趣的特性，如在 SmCPA 和柱状相中由场诱导的手性反转、由场诱导的清除温度升高、二阶相变 Colob → SmCPA 或可逆的场诱导相变 Colob → SmCPF。在对孤立分子进行理论计算和分子动力学模拟的基础上，讨论了连接基团方向意想不到的强烈影响。
• Mesomorphic compound having beta-hydroxycarboxyl group as chiral source and liquid crystal composition
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP0321984A1

  公开（公告）日：1989-06-28

  Disclosed is a mesomorphic compound having a β-hydroxycarboxyl group as the chiral source, which is represented by the formula: wherein m and n are integers of from 1 to 18, X1 and X2 independently represent fluorine, chlorine or hydrogen, Y represents or -O-, Z represents a direct bond, -CH20, or -OCH2-, and * indicates the asymmetric carbon atom. The mesomorphic compound is valuable as a ferroelectric liquid crystal or an additive to a ferroelectric liquid crystal or to a compound showing the SmC phase and having no chiral group.

  本发明公开了一种以β-羟基羧基为手性源的中间体化合物，其结构如式所示： 其中 m 和 n 是 1 至 18 的整数，X1 和 X2 独立地代表氟、氯或氢，Y 代表 或-O-，Z 代表直接键、 -CH20，或 -OCH2-，* 表示不对称碳原子。介形化合物作为铁电液晶或铁电液晶添加剂或显示 SmC 相且无手性基团的化合物非常有价值。