4-bromo-4'-decyloxybiphenyl | 138567-31-4

• 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-bromo-4'-decyloxybiphenyl
• 英文别名: 4-decyloxy-4'-bromobiphenyl；1-bromo-4-(4-decoxyphenyl)benzene
• CAS: 138567-31-4
• 化学式: C₂₂H₂₉BrO
• 分子量: 389.376
• InChiKey: VILGWIYOEOBZFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-4'-decyloxybiphenyl 在 四(三苯基膦)钯 、 正丁基锂 、 硼酸三异丙酯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 苯 为溶剂， 反应 33.0h， 生成 3-[4-(4-Decoxyphenyl)phenyl]cyclohex-2-en-1-one
  参考文献：
  名称：

  Highly efficient syntheses of 3-aryl-2-cycloalken-1-ones and an evaluation of their liquid crystalline properties

  摘要：

  Cycloalkenones are shown to be mesogens and can be synthesised in near quantitative yields by a convergent palladium(0)-catalysed cross-coupling strategy; a 2-methyl group induces a change of phase from smectic to nematic. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00620-3
• 作为产物：
  描述：

  癸基溴 、 4-羟基-4'-溴联苯 生成 4-bromo-4'-decyloxybiphenyl
  参考文献：
  名称：

  手性联苯乙炔近晶型液晶

  摘要：

  标准的Sonogashira偶联从商业上可获得的4-（4'-溴苯基）苯酚开始，提供被不同的手性烷氧基链取代的棒状，苯乙炔延伸的联苯液晶元。取决于由吸电子端基确定的手性中心的位置和靶分子的极性，形成不同类型的近晶液晶。液晶相通过偏振光学显微镜，差示扫描量热法和X射线衍射充分表征。在两种情况下，分子手性被转移到超分子组装体，这通过在手性中间相中的圆二色性测量来证明。

  DOI：

  10.1021/jp1004727

文献信息

• Liquid crystal compounds, mixtures and devices
  申请人：The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland Defence Evaluation Research Agency

  公开号：US06337420B1

  公开（公告）日：2002-01-08

  An electroclinic device having two spaced cell walls each bearing electrode structures and treated on at least one facing surface with an alignment layer, a layer of a smectic liquid crystal material enclosed between the cell walls, where the liquid crystal material contains one or more of the compounds described by formula I as defined in the specification.

  具有两个间隔的细胞壁的电动设备，每个电极结构都带有电极结构，并在至少一个面对表面上用对准层进行处理，一层层状液晶材料被封装在细胞壁之间，液晶材料含有本说明书中定义的I公式描述的一种或多种化合物。
• Synthesis and liquid-crystalline properties of novel laterally connected twins: the influence of the connecting topology and the length of the rigid core
  作者：Jens Andersen、Carsten Tschierske、Siegmar Diele、Dirk Lose

  DOI：10.1039/jm9960601297

  日期：——

  Laterally ligated p-terphenyl twins containing 2-oxapropylene spacers have been synthesized. Their liquid-crystalline properties were investigated by polarizing microscopy, calorirnetry and X-ray scattering. The mesophase stability depends strongly on the topology of connection. It was found that the connection of the mesogenic units at the peripheries of the rigid cores gave twins with the highest clearing temperatures and the broadest smectic C (SC) ranges. Shifting the connecting units to the middle of the rigid cores diminished their mesophase stability. The X-ray investigations indicated that the thickness of the smectic layer was nearly independent of the position of the lateral connecting group when the same mesogens were linked. Also, twins incorporating a 1,4-disubstituted phenyl ring and a biphenyl rigid core have been prepared and they were found to exhibit broad mesomorphic ranges. Another kind of twins was obtained by the lateral–terminal connection of a p-terphenyl rigid core and a 2,5-diphenyl-l,3,4-thiadiazole calamitic unit. Again, a remarkable influence of the connecting position was observed.

  含有2-氧代丙烯间隔基的侧向键合p-三联苯双晶已被合成。通过偏光显微镜、量热法和X射线散射研究了它们的液晶性质。中相稳定性强烈依赖于连接的拓扑结构。发现将介晶单元在刚性核的周边连接产生了具有最高清亮点温度和最宽向列相C（SC）范围的双晶。将连接单元移至刚性核的中间会降低它们的中相稳定性。X射线研究表明，当相同的介晶相连时，向列相层的厚度几乎与侧向连接基团的位置无关。此外，还制备了包含1,4-二取代苯环和联苯刚性核的双晶，发现它们展现出宽广的介晶范围。通过p-三联苯刚性核和2,5-二苯基-1,3,4-噻二唑棒状单元的侧向-末端连接，获得了另一种双晶。再次观察到连接位置的显著影响。
• Synthesis and thermotropic liquid crystalline properties of calamitic molecules with laterally attached hydrophilic groups: Y-shaped three-block molecules which can form smectic and columnar mesophases
  作者：Rene Plehnert、Jörg Andreas Schröter、Carsten Tschierske

  DOI：10.1039/a803043j

  日期：——

  The synthesis and the thermotropic liquid crystalline properties of calamitic mesogens (p-terphenyl derivatives, a biphenyl and a p-quintaphenyl derivative) with a laterally attached hydrophilic group (1,2-diol groups, primary and secondary amides, polyether chains, crown ether units, carbohydrate units, a hydrazide, a quaternary ammonium salt, a carboxylic acid and a sodium carboxylate) are reported. The compounds were investigated by means of polarizing microscopy and calorimetry. The influence of the type of the polar group, of the length of the rigid core and the position of the connection of the hydrophilic group with the rod-like rigid core have been investigated. Many of these amphiphilic molecules can form monolayer S A phases. If a sufficient amount of hydrogen bonding is available their mesophase stability can be higher than that of related compounds with other lateral substituents. Rectangular columnar mesophases can be found for compounds with rather large and flexible polar lateral substituents (polyether chains) fixed to the center of the rigid terphenyl unit. These columnar phases should represent ribbon phases resulting from the collapse of the smectic layers (modulated smectic phases). The proposed model is also related to that suggested for supermolecular structures of triblock copolymers. Thus, these molecules can be regarded as low molecular weight block compounds consisting of three different and incompatible molecular parts.

  报道了带有侧向亲水基团（如1,2-二醇基、初级和次级酰胺、聚醚链、冠醚单元、糖单位、肼、季铵盐、羧酸和钠盐）的柱状液晶 (p-三苯基衍生物、联苯和p-五苯基衍生物) 的合成及其热驱动液晶特性。通过偏振光显微镜和热量计对这些化合物进行了研究。探讨了极性基团的类型、刚性核心的长度以及亲水基团与杆状刚性核心连接位置的影响。这些两性分子中的许多可以形成单层 S_A 相。如果有足够的氢键相互作用，它们的介相稳定性可能高于其他侧向取代基的相关化合物。对于那些带有较大且灵活的极性侧向取代基（聚醚链）并固定在刚性三苯基单元中心的化合物，可以观察到矩形柱状介相。这些柱状相应代表了由层状相 collapse 所形成的带状相（调制层状相）。所提出的模型也与对三嵌段共聚物超分子结构的建议相关。因此，这些分子可以被视为由三部分不同且不相容的低分子量嵌段化合物。
• Liquid Crystalline Oligosilanes with Alkoxybiphenyl Groups
  作者：Tetsuo Yatabe、Yuji Sasanuma、Akira Kaito、Yoshikazu Tanabe

  DOI：10.1246/cl.1997.135

  日期：1997.2

  Oligosilane derivatives, ROC12H8(SiMe2)nC12H8OR, were synthesized by treatment of α,ω-dichloropermethyloligosilanes with Grignard reagents derived from 4-alkoxy-4′-bromobiphenyls. Oligosilanes with n = 6; R = C8H17 and n = 6; R = C10H21 showed smectic B and E phases, respectively.

  通过用来自 4-alkoxy-4′-bromobiphenyls 的格氏试剂处理 α,ω-二氯二甲基低聚硅烷，合成了低聚硅烷衍生物 ROC12H8(SiMe2)nC12H8OR。n = 6; R = C8H17 和 n = 6; R = C10H21 的寡硅烷分别呈现出 B 相和 E 相。
• Chiral Biphenylacetylene Smectic Liquid Crystals
  作者：Laura de Vega、Pedro D. Ortiz、Gunther Hennrich、Ana Omenat、Rosa M. Tejedor、Joaquín Barberá、Berta Gómez-Lor、José Luis Serrano

  DOI：10.1021/jp1004727

  日期：2010.4.15

  phenylacetylene extended biphenyl mesogens substituted with different chiral alkoxy chains, starting from commercially available 4-(4′-bromophenyl)phenol. Depending on the position of the chiral center and the polar nature of the target molecules as determined by the electron withdrawing end-groups, different types of smectic liquid crystals are formed. The liquid crystal phases are fully characterized

  标准的Sonogashira偶联从商业上可获得的4-（4'-溴苯基）苯酚开始，提供被不同的手性烷氧基链取代的棒状，苯乙炔延伸的联苯液晶元。取决于由吸电子端基确定的手性中心的位置和靶分子的极性，形成不同类型的近晶液晶。液晶相通过偏振光学显微镜，差示扫描量热法和X射线衍射充分表征。在两种情况下，分子手性被转移到超分子组装体，这通过在手性中间相中的圆二色性测量来证明。