4-(5-(4-(octyloxy)phenyl)-1,3,4-thiadiazol-2-yl)phenol | 121680-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(5-(4-(octyloxy)phenyl)-1,3,4-thiadiazol-2-yl)phenol
• 英文别名: 4-octyloxyphenyl-5-(4-hydroxyphenyl)-1,3,-4-thiadiazole；2-(4-n-Octyloxyphenyl)-5-(4-hydroxyphenyl)-1,3,4-thiadiazole；4-[5-(4-octoxyphenyl)-1,3,4-thiadiazol-2-yl]phenol
• CAS: 121680-07-7
• 化学式: C₂₂H₂₆N₂O₂S
• 分子量: 382.527
• InChiKey: RTEDWPZJOUZDQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-(4-(octyloxy)phenyl)-1,3,4-thiadiazol-2-yl)phenol 、 (-)-(S)-2-methoxy-propionyl chloride 在 4-二甲氨基吡啶 三乙胺 作用下， 以 甲苯 为溶剂， 生成 (S)-2-Methoxy-propionic acid 4-[5-(4-octyloxy-phenyl)-[1,3,4]thiadiazol-2-yl]-phenyl ester
  参考文献：
  名称：

  Tschierske, C.; Joachimi, D.; Zaschke, H., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 191, p. 231 - 235

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-(octyloxy)benzoate 在 劳森试剂 、 palladium 10% on activated carbon 、 氢气 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 108.0h， 生成 4-(5-(4-(octyloxy)phenyl)-1,3,4-thiadiazol-2-yl)phenol
  参考文献：
  名称：

  构成区域异构恶二唑和噻二唑核心的非对称胆固醇二聚体：结构与性质相关性的研究†

  摘要：

  通过将促生胆固醇与衍生自取代的1,3,4-恶二唑或1,2,4-恶二唑或1,3,4-噻二唑部分的弯曲结构连接，制备了三个系列的手性非对称二聚体。这两个介晶链段通过长度和奇偶性不同的间隔子相互连接。弯曲的非手性单元的结构随中央杂环的不同而系统地变化，以了解弯曲角度对热和胶凝行为的影响。由杂环核决定的非手性单元的弯曲角在受挫相的稳定中起主要作用。基于1,3,4-恶二唑单元的二聚体具有更弯曲的结构，可稳定受挫相（如蓝相和扭曲晶界相）。具有较大弯曲角度的弯曲系统优选用于稳定手性向列相和近晶A相。有趣的是，与基于1,3,4-恶二唑单元的二聚体一样，增加的弯曲结构降低了中间相的稳定性，在该二聚体中，许多化合物均表现出单相相。在具有较大弯曲角的二聚体的情况下，观察到对映的同构。所有化合物在溶液中均显示蓝光发射。在这些手性二聚体中，只有基于1,3,4-恶二唑单元的化合物才具有胶凝能力，这强调了弯曲角度，偶极

  DOI：

  10.1039/c6nj03141b

文献信息

• 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。
• Liquid-crystalline allene derivatives
  作者：Kerstin Zab、Holger Kruth、Carsten Tschierske

  DOI：10.1039/cc9960000977

  日期：——

  The synthesis of the first liquid-crystalline allene derivatives with chiral smectic C-phases is reported.

  报道了第一种具有手性层状C相的液晶全烯衍生物的合成。
• Axial chiral allenylacetates as novel ferroelectric liquid crystals
  作者：Ralph Lunkwitz、Carsten Tschierske、Arne Langhoff、Frank Gießelmann、Peter Zugenmaier

  DOI：10.1039/a701032j

  日期：——

  Liquid crystalline alkane-3,4-dienoates (allenylacetates) have been synthesized. Most compounds incorporate a heterocyclic 1,3,4-thiadiazole ring or a pyrimidine ring as a constituent of the rigid core. These axial chiral allene derivatives were at first obtained as racemic mixtures. Some of them were also synthesized in enantiomerically enriched form by enantioselective synthesis. The compounds were investigated by polarizing microscopy and by differential scanning calorimetry. The three-ring compounds exhibit broad regions of smectic C-phases. The optically active three-ring compounds show broad S c *-phases with moderate values of spontaneous polarization.

  液晶烷烃-3,4-二烯酸盐（烯基乙酸盐）已被合成。大多数化合物的刚性核心都包含一个杂环 1,3,4-噻二唑环或一个嘧啶环。这些轴向手性烯衍生物最初是以外消旋混合物的形式获得的。其中一些还通过对映体选择性合成获得了对映体富集形式。这些化合物通过偏光显微镜和差示扫描量热法进行了研究。三环化合物呈现出宽广的胶状 C 相区域。具有光学活性的三环化合物显示出宽广的 S c * 相，自发极化值适中。
• Ferroelectric Liquid Crystals Having Various Cores. Effect of Core Structure on Physical Properties
  作者：Shin-ichi Sugita、Susumu Toda、Tetsuo Yamashita、Tsutomu Teraji

  DOI：10.1246/bcsj.66.568

  日期：1993.2

  Ferroelectric liquid crystals (FLC’s) having various cores were synthesized and the effect of the different core structures on the spontaneous polarization (Ps) values was investigated. The results indicate that the core structure has a great influence on the Ps value and introduction of a heterocycles such as pyrimidine and thiadiazole ring in the core increases the Ps value. Moreover, several compounds in this series are interesting as chiral dopants for FLC, because the mixtures containing them showed superior properties as FLC mixture.

  合成了具有各种核的铁电液晶（FLC），并研究了不同核结构对自发极化（Ps）值的影响。结果表明，核心结构对Ps值影响很大，在核心中引入嘧啶环、噻二唑环等杂环可提高Ps值。此外，该系列中的几种化合物作为 FLC 的手性掺杂剂很有趣，因为含有它们的混合物显示出作为 FLC 混合物的优异性能。
• Use of the chiral group (1S, 4R)-1,4-dihydroxy-2-cyclopentenyl in the
  申请人：BASF Aktiengesellschaft

  公开号：US05543076A1

  公开（公告）日：1996-08-06

  The chiral group of the formula ##STR1## is used as a constituent of liquid-crystalline compounds.

  化学式##STR1##的手性群被用作液晶化合物的组成部分。