4-hexadecyloxy-2-hydroxybenzaldehyde | 52123-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hexadecyloxy-2-hydroxybenzaldehyde
• 英文别名: 4-n-hexadecyloxy-2-hydroxybenzaldehyde；4-(Hexadecyloxy)-2-hydroxybenzaldehyde；4-hexadecoxy-2-hydroxybenzaldehyde
• CAS: 52123-16-7
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: XKZMLDMOWAWWLP-UHFFFAOYSA-N

物化性质

• 沸点：
  478.7±25.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hexadecyloxy-2-hydroxybenzaldehyde 在 盐酸肼 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以62%的产率得到6,6'-(1E,1'E)-hydrazine-1,2-diylidenebis(methan-1-yl-1-ylidene)bis(3-hexa decyloxyphenol)
  参考文献：
  名称：

  The π–π interactions enhanced in salicylaldimines and salicylaldazines

  摘要：

  Four new series of salicylaldazines 1 and salicylaldimines 2-4 were prepared, characterized and their mesomorphic properties were studied. The structures of all compounds were identified and confirmed by spectroscopic techniques such as H-1, C-13 NMR, MS and elemental analysis. Three single crystallographic structures of compounds la (n=3, 6) and 2 (n=3) were determined by X-ray analysis in order to correlate the molecular structures with the formation of mesophases. Crystallographic data indicated that the better mesomorphic properties might be controlled by CH-pi, pi-pi or/and H-bonds in such system. Except for crystalline compounds 4, all other compounds 1-3 showed mesomorphic behavior of nematic, smectic A or/and smectic C phases, which were characterized by differential scanning calorimetry, optical polarizing microscope and X-ray diffraction experiments. All compounds 1-4 showed yellow green photoluminescence in THF occurred at 519-521 nm. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.049
• 作为产物：
  描述：

  对甲苯磺酸十六烷基酯 、 水杨醛 以 乙醇 为溶剂， 反应 12.0h， 生成 4-hexadecyloxy-2-hydroxybenzaldehyde
  参考文献：
  名称：

  Kister, Jacky; Pommier, Henri Paul; Metzger, Jacques, Canadian Journal of Chemistry, 1984, vol. 62, p. 2372 - 2378

  摘要：

  DOI：

文献信息

• Observation of polar order and thermochromic behaviour in a chiral bent-core system exhibiting exotic mesophases due to superstructural frustration
  作者：Vidhika Punjani、Golam Mohiuddin、Supreet Kaur、Raj Kumar Khan、Sharmistha Ghosh、Santanu Kumar Pal

  DOI：10.1039/c7cc08885j

  日期：——

  First examples of smart bent-core materials that exhibited frustrated structures with high polar order and thermochromism.

  首次展示了具有高极性序和热致变色性质的智能弯曲核材料的示例。
• Induction of Mesomorphism through Supramolecular Assembly in Metal Coordination Compounds of “salphen”‐Type Schiff Bases: Photoluminescence and Solvatochromism
  作者：Sutapa Chakraborty、Paritosh Mondal、S. Krishna Prasad、D. S. Shankar Rao、Chira R. Bhattacharjee

  DOI：10.1002/ejic.201600513

  日期：2016.10

  variable-temperature powder X-ray diffraction (XRD). The Schiff base ligands are non-mesomorphic; however, coordination to NiII and ZnII ions induces columnar mesomorphism, this being stable down to room temperature in the latter case. Interestingly, the complexes of CuII and VOIV did not show any mesomorphism. The free ligands and the ZnII complexes are luminescent both in the condensed state and in solution

  金属（VO2+、Ni2+、Cu2+ 和 Zn2+）配位引起的介晶现象及其对新系列对称“salphen”型 N,N-双（4-n-烷氧基水杨烯）-4,5-二氯光物理性质的影响-1,2-苯二胺配体 (n = 12, 14, 16) 具有高负电间隔取代基和不同长度的烷氧基臂已被研究。介晶现象已通过偏光显微镜 (POM)、差示扫描量热法 (DSC) 和变温粉末 X 射线衍射 (XRD) 进行了探测。席夫碱配体是非介晶的；然而，与 NiII 和 ZnII 离子的配位诱导柱状介晶现象，这在后一种情况下在室温下稳定。有趣的是，CuII 和 VOIV 的配合物没有表现出任何介晶现象。游离配体和 ZnII 复合物在凝聚态和溶液中都发光，凝聚态的发射最大值相对于溶液中的发射最大值显着红移。在使用 GAUSSIAN 09 程序的 DFT 研究中，确定代表性 ZnII 复合物的能量优化结构是扭曲的方形平面。ZnII
• Polarization effect in luminescent mesogenic BF2 complexes derived from heterocyclic benzothiazoles
  作者：Yuan−Chun Hsu、Chun−Yang Wang、Pei−Chi Hsiao、Yi-Hong Cai、Gene−Hsiang Lee、Chung K. Lai

  DOI：10.1016/j.molliq.2019.111660

  日期：2020.1

  Two series of benzo(thia)xazoles 1–2 and one series of boron difluoride complexes 2-BF2 derived from benzothiazoles 2 were reported, and their mesomorphic and optical properties were investigated. The crystal and molecular structures of compound 2 and 2-BF2 (all n = 8) were determined by means of X-ray structural analysis, and both crystallize in the triclinic P-1 and monoclinic P21/c. The geometry

  两个系列苯并（硫杂）的xazoles 1-2和一个串联二氟化硼络合物的2-BF 2从苯并噻唑衍生的2报道，他们的介晶和光学性能进行了研究。 通过X射线结构分析确定化合物2和2-BF 2（全部n＝ 8）的晶体和分子结构，并且都在三斜晶系P-1和单斜晶系P 2 1 / c中结晶。硼中心的几何形状完全是四面体，整体分子形状被认为是棒状。苯并（thia）xazoles 1和2表现出N或/和SmC相，硼配合物2-BF 2形成N或/和SmC相。苯并噻唑2的中间相温度范围比苯并恶唑1宽得多，这归因于掺入的硫原子具有更好的极化作用。硼配合物2-BF 2（n  = 10，12） 在CH 2 Cl 2中在λmax = 569–571 nm处发射出黄绿色发射光。这是第一个衍生自苯并噻唑的介晶BF 2配合物。
• Liquid crystalline properties of bis(salicylaldiminato)copper(II) complexes: the first columnar discotics derived from salicylaldimine Schiff bases
  作者：Chung K. Lai、Chung-hsiung Chang、Chun-hsien Tsai

  DOI：10.1039/a707091h

  日期：——

  The synthesis and mesomorphic properties of a homologous series ofN-(2-hydroxy-4-n-alkoxybenzylidene)-3′,4′-di-n-alkoxylanilines and their copper(ii) complexes bis[(N-3′,4′-dialkoxyphenyl)-4-n-alkoxylsalicylaldiminato]copper(ii) are reported. The disc-like copper complexes exhibited columnar hexagonal disordered mesophases, which were characterized by DSC analysis and optical polarized microscopy. The structure of the mesophases was confirmed by X-ray powder diffraction (XRD). The mesomorphic properties for these copper complexes were compared with other similar metallomesogenic bis(salicylaldiminato)copper(ii) complexes in terms of molecular structural differences.

  报道了一组N-(2-羟基-4-正烷氧基苯亚甲基)-3′,4′-二-正烷氧基苯胺及其铜(II)配合物双[(N-3′,4′-二烷氧基苯基)-4-正烷氧基水杨醛亚胺]铜(II)的合成与液晶性质。盘状铜配合物表现出无序的柱状六方相，通过差示扫描量热分析和偏光显微镜进行了表征。通过X射线粉末衍射(XRD)确定了其相结构。与其他类似的金属配位液晶双(水杨醛亚胺)铜(II)配合物相比，这些铜配合物的液晶性质与其分子结构差异有关。
• Zinc(II)-salphen complexes bearing long alkoxy side arms: Synthesis, solvent dependent aggregation, and spacer group substituent effect on mesomorphism and photophysical property
  作者：Sutapa Chakraborty、Paritosh Mondal、S. Krishna Prasad、D.S. Shankar Rao、Chira R. Bhattacharjee

  DOI：10.1016/j.molliq.2017.09.078

  日期：2017.11

  substitution at the ligand's spacer; different variant of columnar phases were exhibited by the ligands and the zinc(II) complexes. The ligands and the complexes displayed fluorescence at ambient temperature in the blue-green region with moderate to low intensity. Density functional theory (DFT) calculations indicated a distorted square-planar geometry around the zinc(II) center in the complexes. The coordinative

  两个新的卤素取代的“ salphen”型席夫碱配体[ZnL]的半圆盘形锌（II）配合物；H 2 L = [ N，N'-双（4-n-烷氧基水杨基）-4-氟/溴-1,2-二氨基苯]（n = 12、14、16）已合成，并研究了它们的同构和光物理性质。配体和锌（II）配合物在更宽的温度范围内显示出柱状中间相。取决于配体间隔基上的卤素取代基；配体和锌（II）配合物表现出不同的柱状相变体。配体和配合物在环境温度下在蓝绿色区域中以中等至低强度显示荧光。密度泛函理论（DFT）计算表明，配合物中锌（II）中心周围的方形几何结构变形。这些配合物中锌（II）中心的配位不饱和度会导致在非配位溶剂的稀溶液中产生有趣的聚集性质。但是，在协调溶剂时，