3-(4-tetradecanoxyphenyl)pyrazole | 483987-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-tetradecanoxyphenyl)pyrazole
• 英文别名: 3-(4-(tetradecyloxy)phenyl)-1H-pyrazole；5-(4-tetradecoxyphenyl)-1H-pyrazole
• CAS: 483987-46-8
• 化学式: C₂₃H₃₆N₂O
• 分子量: 356.552
• InChiKey: MWVNUDCTKWUDFE-UHFFFAOYSA-N

物化性质

• 沸点：
  514.0±33.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-tetradecanoxyphenyl)pyrazole 在 四氟硼酸-二乙醚络合物 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  Pyrazolium salts as a new class of ionic liquid crystals

  摘要：

  新的烷氧基苯基取代的吡唑鎓盐 [H2pzR(n)][A] (R(n) = C6H4OCnH2n+1; n = 8, 10, 12, 14, 16, 18; [A] = Cl−, BF4−, ReO4− 、SbF6−、CF3SO3−、CH3-p-C6H4SO3−) 已被合成并表征。那些含有 Cl−、BF4−、ReO4− 和 SbF6− 阴离子的化合物表现为呈现近晶 A (SmA) 中间相的液晶化合物。由于中性吡唑前体 [HpzR(n)] 不是液晶，因此它们的质子化和抗衡阴离子的策略选择有助于实现介晶化和调节转变温度，从而产生了一类新型离子液晶。作为每种类型化合物的代表性实例的选定衍生物的 X 射线晶体结构已得到解析。在大多数情况下，出于 X 射线目的，盐被设计为含有一种甲氧基苯基取代的吡唑鎓阳离子。根据阴离子的性质，发现了不同的结构特征。通过氢键保持的二聚体单元排列成链，这些链以层状阵列形式堆积在化合物 [H2pzR(10)][BF4]、[H2pzR(1)][OTf] 和 [H2pzR(1)][PTS] 中，但[H2pzR(1)][Cl]和[H2pzR(1)][ReO4]发现了二维结构。提出了固体和中间相结构之间的关系。 CF3SO3− 和 CH3-p-C6H4SO3− 衍生物缺乏介晶现象也可以根据主要结构特征进行解释。

  DOI：

  10.1039/c2jm31939j
• 作为产物：
  描述：

  1-(4-tetradecyloxyphenyl)-3-hydroxy-2-propen-1-one 在 盐酸 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 12.08h， 生成 3-(4-tetradecanoxyphenyl)pyrazole
  参考文献：
  名称：

  Calamitic metallomesogens derived from unsymmetric pyrazoles

  摘要：

  Three series of copper(II) complexes 1a-1c derived from unsymmetric pyrazoles 2a-2c were prepared and their mesomorphic properties investigated. The mesomorphic behavior of compounds was studied by differential scanning calorimetry, polarizing optical microscopy, and powder X-ray diffractometry. The crystal and molecular structures of mesogenic copper complex (2a; n=10) of 3-[4-decyloxyphenyl]-1H-pyrazole were determined by means of X-ray structural analysis. It crystallizes in the triclinic space group p-1, with a=4.0890(1) angstrom, b=18.0167(2) angstrom, c=25.5015(5) angstrom, and Z=2. The geometry at copper center was not perfectly square planar. A weak intermolecular H-bond (d=2.36 angstrom) between Cl1 and H2 atoms and pi-pi interaction (ca. 3.45-3.55 angstrom) was also observed. All their precursors 2a-2c were not mesogenic. In contrast. copper complexes 1a formed nematic or smectic C phases and complexes 1b-1c formed crystalline phases. Powder X-ray diffraction experiments confirmed the presence of SmC phase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.062

文献信息

• Silver pyrazole complexes with tunable liquid crystals and luminescent properties
  作者：María José Mayoral、Paloma Ovejero、José Antonio Campo、José Vicente Heras、María Rosario Torres、Carlos Lodeiro、Mercedes Cano

  DOI：10.1039/b9nj00753a

  日期：——

  CH3-p-C6H4SO3− (PTS), CF3SO3− (OTf)) (type II), containing monosubstituted pyrazole ligands, are not mesomorphic but also behave as luminescent materials. The crystalline structures of 5 and 10, as representative examples of classes I and II, have been solved. Molecular “H” or “Z” shapes, depending on the cis or trans orientation of the NH groups of the pyrazole ligands, were found, respectively. The first type

  新的 银 基于的离子络合物 吡唑 类型的配体 [Ag（HPZ 2R（n））2 ] [A]（HPZ 2R（Ñ） = 3,5-双（4-烷氧基苯基）吡唑; R = C 6 H ^ 4 OC ñ ħ 2 Ñ 1 ; [A] = CH 3 - p -C 6 H ^ 4 SO 3 - （PTS），CF 3 SO 3 -（OTF））（类型我）是在固体状态下表现出光致发光，在溶液中和在中间相的液晶材料。相比之下，相关的同行[Ag（HPZ R（n））2 ] [A]（HPZ R（Ñ） = 3-（4-烷氧基苯基）吡唑; R = C 6 H ^ 4 OC ñ ħ 2 Ñ 1 ; [A] = CH 3 - p -C 6 H ^ 4 SO 3 -（PTS）， CF 3 SO 3 -（OTF））（类型II），含单取代吡唑配体不是介晶的，但也表现为发光材料。作为I和II类的代表性实例，已经解决了5和10的晶体结构。分子“
• Silver and gold luminescent metallomesogens based on pyrazole ligands
  作者：María José Mayoral、Paloma Ovejero、José Antonio Campo、José Vicente Heras、Elena Pinilla、María Rosario Torres、Carlos Lodeiro、Mercedes Cano

  DOI：10.1039/b808487d

  日期：——

  A series of ionic bis(pyrazole)-silver(I) and -gold(I) complexes [ML2][A] (M = Ag, Au; A = BF4−, PF6−, NO3−), prepared by coordination of the mesomorphic L = Hpz2R(n) or non-mesomorphic L = HpzR(n) pyrazole ligands (Hpz2R(n) = 3,5-bis(4-alkyloxyphenyl)pyrazole; HpzR(n) = 3-(4-alkyloxyphenyl)pyrazole), has been studied. The complexes exhibit enantiotropic behaviour, showing smectic A (SmA) mesophases. The choice of the ligands allows the achievement of ‘H’ or ‘U’ molecular shapes, which appear to be responsible for the attainment of liquid crystal mesophases, these not being dependent on the coordinating or non-coordinating nature of the A counteranions. The new complexes are photoluminescent both in the solid state and in solution at room temperature. In addition, the luminescent behaviour of selected compounds as a function of the temperature indicates that the luminescence is maintained in the mesophase.

  一系列离子型双（吡唑）-银（I）和-金（I）配合物[ML2][A]（M = Ag, Au；A = BF4-、PF6-、NO3-）配位制备的中形态 L = Hpz2R(n) 或非中形态 L = HpzR(n) 吡唑配体（Hpz2R(n) = 3,5-双(4-烷氧基苯基)吡唑；HpzR(n) = 3-(4-烷氧基苯基)吡唑）。这些配合物表现出各向异性，呈现出 Smectic A (SmA) 介相。配体的选择可以实现 "H "或 "U "分子形状，这似乎是实现液晶介相的原因，而这些并不取决于 A 反阳离子的配位或非配位性质。在室温下，这些新复合物在固态和溶液中都能发光。此外，所选化合物的发光行为与温度的函数关系表明，发光在介相中得以保持。
• Luminescence of neutral and ionic gold(I) complexes containing pyrazole or pyrazolate-type ligands
  作者：Paloma Ovejero、María José Mayoral、Mercedes Cano、María Cristina Lagunas

  DOI：10.1016/j.jorganchem.2006.12.025

  日期：2007.3

  the Hpz or pz− ligands, the pattern of bands of compounds being related with the molecular structure and/or the nature of the ligands. The thermal behaviour of several complexes of the types III, IV and V containing long-chain substituents (n ⩾ 12) was examined by polarising light optical microscopy (POM). The derivative [AuCl(HpzR(12))] was proved to have liquid crystal properties exhibiting a mesophase

  一系列吡唑（HPZ）和吡唑特（PZ - ）金（I）的类型的配合物[AU（HPZ 2R（Ñ））（PPH 3）] +（我），[AU（HPZ 2R（Ñ））2 ] +（II），[Au（μ-PZR （n））] 3（III），[Au（PZ R（n）/ 2R（n））（PPh 3）]（IV），[AuCl（HPZ R （n）/ 2R（n））]（V）和[（PPh3）Au（μ-PZR （n））Au（PPh 3）] +（VI），R（n）和2R（n）表示在3或3位的C 6 H 4 OC n H 2 n +1取代基分别显示杂环的3位和5位在77 K时呈固态发光，而与金属间Au-Au相互作用的存在与否无关。所有配合物的发射光谱均由395–500 nm范围内的结构能带组成，这归因于涉及HPZ或PZ的配体-金属电荷转移（LMCT）跃迁-配体，化合物带的模式与配体的分子结构和/或性质有关。该类型的多个复合物的热行为III，I
• Pyrazole-based allylpalladium complexes: Supramolecular architecture and liquid crystal behaviour
  作者：M.C. Torralba、M. Cano、J.A. Campo、J.V. Heras、E. Pinilla、M.R. Torres

  DOI：10.1016/j.inoche.2006.07.043

  日期：2006.12

  The co-ordination of non-mesomorphic 3-substituted pyrazoles Hpz(R) to the [Pd(eta(C3H5)-C-3)](+) fragment gives rise to four-coordinated complexes [Pd(eta(3)-C3H5)(Hpz(R))(2)](+) (R = C6H4OCnH2n+1; n = 12 (I-12), 14 (I-14), 16 (I-16), 18 (I-18)), which were isolated with BF4- as counteranion. The new complexes are proved to have liquid crystal properties exhibiting monotropic or enantiotropic smectic A (SmA) mesophases at low temperatures which range between ca. 40 and 80 degrees C. The crystal structure of I-12 presents a 2D network highly interdigitated, which could be related with the layered structure proposed in the liquid crystalline phase through the X-ray diffraction at variable temperature. (C) 2006 Elsevier B.V. All rights reserved.