3-[4-octyloxyphenyl]-1H-pyrazole | 385433-40-9

• 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-octyloxyphenyl]-1H-pyrazole
• 英文别名: 3-(4-n-octyloxyphenyl)pyrazole；5-[4-(Octyloxy)phenyl]-1H-pyrazole；5-(4-octoxyphenyl)-1H-pyrazole
• CAS: 385433-40-9
• 化学式: C₁₇H₂₄N₂O
• 分子量: 272.39
• InChiKey: BPCXUIJRKBTFKN-UHFFFAOYSA-N

物化性质

• 沸点：
  444.6±28.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-octyloxyphenyl]-1H-pyrazole 在 盐酸 、 silver(I) 4-methylbenzenesulfonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 3-(4-(octyloxy)phenyl)-1H-pyrazole 4-methylbenzenesulfonate
  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-辛氧基苯基)-3-羟基-2-丙烯-1-酮 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-octyloxyphenyl]-1H-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

• Polymorphism and metal–metal interactions on [Rh(Cl)(CO)2(HpzR)] complexes
  作者：M.C. Torralba、M. Cano、J.A. Campo、J.V. Heras、E. Pinilla、M.R. Torres

  DOI：10.1016/s0022-328x(01)01058-0

  日期：2001.8

  have been isolated for [Rh(Cl)(CO)2(Hpzdp)] (12) in contrast to the single red crystalline form isolated for the related complexes [Rh(Cl)(CO)2(HpzR)] (R=hp, op; 10 and 11). X-ray crystal structures of the red forms of 10–12 as well as the yellow one of 12 have been solved. The red compounds display one-dimensional stacking of square-planar molecules with metal–metal interactions along the c-axis. The

  含有3- [4-正己氧基苯基]（hp），3- [4-正辛氧基苯基]（op）和3- [4-正癸氧基苯基]（dp）取代基，Hpz R（R = hp ，运算，DP; 1 - 3），以及它们相应的Rh（I）化合物的[Rh（CL）（LL）（HPZ - [R）]（LL = 2,5-降冰片二烯NBD，1,5-环辛二烯COD，2CO; R = hp，op，dp; 4 – 12）已经准备好并进行了表征。分析了吡唑取代基对Rh（I）配合物性能的影响。[Rh（Cl）（CO）2（Hpz dp）]的两种结晶多晶型物（黄色和红色）已被分离（12）与相关配合物[Rh（Cl）（CO）2（Hpz R）]分离的单一红色结晶形式相反（R = hp，op；10和11）。的红色形式的X射线晶体结构10 - 12以及的黄色一个12已被解决。红色化合物显示沿c方向具有金属-金属相互作用的方平面分子的一维堆积-轴。黄色形式由通过Cl桥连
• 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
• Calamitic metallomesogens derived from unsymmetric pyrazoles
  作者：Min-Chou Chen、Shih-Chieh Lee、Chia-Chung Ho、Tarng-Shiang Hu、Gene-Hsiang Lee、Chung K. Lai

  DOI：10.1016/j.tet.2009.08.062

  日期：2009.11

  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.
• Pyrazolium salts as a new class of ionic liquid crystals
  作者：Ignacio Sánchez、José Antonio Campo、José Vicente Heras、M. Rosario Torres、Mercedes Cano

  DOI：10.1039/c2jm31939j

  日期：——

  New alkyloxyphenyl substituted pyrazolium salts [H2pzR(n)][A] (R(n) = C6H4OCnH2n+1; n = 8, 10, 12, 14, 16, 18; [A] = Cl−, BF4−, ReO4−, SbF6−, CF3SO3−, CH3-p-C6H4SO3−) have been synthesised and characterised. Those containing Cl−, BF4−, ReO4− and SbF6− anions behave as liquid crystal compounds exhibiting smectic A (SmA) mesophases. Because the precursor neutral pyrazoles [HpzR(n)] were not liquid crystals, their protonation and strategic choice of the counter-anion was found useful to achieve mesomorphism and to modulate the transition temperatures, so giving rise to a new class of ionic liquid crystals. The X-ray crystal structures of selected derivatives as representative examples of each type of compound have been resolved. In most of the cases, for X-ray purposes, the salts were designed to contain one methoxyphenyl-substituted pyrazolium cation. Different structural features have been found depending on the nature of the anion. Dimeric units held through hydrogen bonds are arranged in chains which pack in a layer-like array for compounds [H2pzR(10)][BF4], [H2pzR(1)][OTf] and [H2pzR(1)][PTS], but 2D structures were found for [H2pzR(1)][Cl] and [H2pzR(1)][ReO4]. Relationships between the solid and the mesophase structures are proposed. The absence of mesomorphism for CF3SO3− and CH3-p-C6H4SO3− derivatives is also explained on the basis of the main structural features.

  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。