4-(decyloxy)salicylaldehyde | 68075-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(decyloxy)salicylaldehyde
• 英文别名: 4-decyloxy-2-hydroxybenzaldehyde；4-(Decyloxy)-2-hydroxybenzaldehyde；4-decoxy-2-hydroxybenzaldehyde
• CAS: 68075-69-4
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: QGTMGMLIAOWQLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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-(decyloxy)salicylaldehyde 在 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 bis[methyl 4-(4-(decyloxy)-2-hydroxybenzylideneamino)benzoato]copper(II)
  参考文献：
  名称：

  棒状液晶的合成、表征和介晶研究——4-(4'-(烷氧基)-2-羟基亚苄基氨基)苯甲酸甲酯及其铜(II)和镍(II)配合物

  摘要：

  以极性甲酯为端基的新系列 Schiff 碱介晶配体，4-(4'-(烷氧基)-2 羟基亚苄基氨基)苯甲酸甲酯，CnLH (n = 6, 8, 10, 12, 14, 16)并合成了它们的铜（II）和镍（II）配合物。它们通过元素分析、傅里叶变换红外 (FT-IR)、1H 和 13C 核磁共振以及 UV-VIS 光谱进行表征。通过差示扫描量热法 (DSC) 和偏光显微镜 (POM) 研究了这些化合物的介晶性质。配体表现出具有高温范围和热稳定性的对映性 SmA 中间相。方形平面铜 (II) 配合物显示出对映 SmA 中间相，但镍 (II) 配合物本质上是非介晶的。化合物的热稳定性也通过热重分析确定。使用 GAUSSIAN-03 程序在 B3LYP 级别进行密度泛函理论 (DFT) 计算以获得配体及其金属配合物的稳定电子结构。

  DOI：

  10.1080/15421406.2013.803872
• 作为产物：
  描述：

  间苯二酚 在 sodium hydroxide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 60.5h， 生成 4-(decyloxy)salicylaldehyde
  参考文献：
  名称：

  Novel macro metallomesogens derived from simple dihydroxy benzenes

  摘要：

  A series of tetradentate Schiff base metallomesogenic diols and their model compounds were synthesized from two simple dihydroxy benzenes. The metallomesogenic diol was constructed from three ring containing mesogen linked through ester and azomethine with terminal hydroxy group. This upon complexation with copper(II) formed metallomesogenic diol with varing terminal chain length. The related model metallomesogenic compounds were also synthesized with varying chain length with terminal methyl group and compared the properties with metallomesogenic diols. Extensive characterization of all metallomesogenic compounds and intermediates were carried out by FT-IR, H-1 & C-13 NMR, EPR, VSM, Mass (EI and FAB) and UV-Vis spectroscopy. Hot stage polarizing microscope, Differential scanning calorimetry was used to ensure the phase characteristics such as nature of phase, melting and clearing temperatures and phase range. The appearance of enantiotropic smectic A phases indicated high molecular polarizability of the core due to the metal ion. The role of copper(II) ion on mesogens were discussed. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.12.001

文献信息

• Novel Hydroxy- and Methyl-Terminated Triaromatic Schiff Base Compounds: Synthesis and Mesogenic Properties
  作者：Natarajan Senthilkumar、Tanneru Narasimhaswamy、Aravamudhan Raghavan

  DOI：10.1071/ch09405

  日期：——

  A series of Schiff base hydroxy-mesogens and their model compounds have been synthesized. The mesogen is constructed from three-ring-containing mesogens linked through ester and azomethine groups with a terminal hydroxy group. The related model compounds were also synthesized with varying chain length with a terminal methyl group and their properties were compared with that of hydroxy mesogens. Extensive characterization of all mesogenic compounds was carried out by Fourier-transform IR, 1H and 13C NMR and mass spectroscopy. The phase characteristics such as nature of phase, melting and clearing temperatures and phase range were evaluated using a hot-stage optical polarizing microscope and differential scanning calorimetry. The appearance of enantiotropic smectic phases is due to the high molecular polarizability of the triaromatic core with azomethine and ester linkages.

  我们合成了一系列席夫碱羟基中间体及其模型化合物。中间体是由三环中间体通过酯基和氮甲基与末端羟基连接而成。此外，还合成了带有末端甲基的不同链长的相关模型化合物，并将它们的性质与羟基介原进行了比较。通过傅立叶变换红外光谱、1H 和 13C NMR 以及质谱对所有介源化合物进行了广泛的表征。使用热级光学偏光显微镜和差示扫描量热仪对相的性质、熔化和清除温度以及相范围等相特性进行了评估。出现各向对映胶凝相的原因是具有偶氮甲基和酯连接的三芳香族核心具有高分子极化性。
• 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。
• Nematic phases in achiral unsymmetrical four-ring bent-core azo compounds possessing strongly polar cyano and nitro moieties as end substituents: Synthesis and characterization
  作者：Somen Debnath、Golam Mohiuddin、Srikanth Turlapati、Nazma Begum、Dipika Debnath Sarkar、V.S. Nandiraju Rao

  DOI：10.1016/j.dyepig.2013.05.029

  日期：2013.11

  transverse direction of the molecule. The molecular structure characterization is consistent with elemental and spectroscopic analysis data. The materials thermal behaviour and phase characterization have been investigated by differential scanning calorimetry and polarizing optical microscopy. All the compounds exhibit enantiotropic nematic phase over a wide temperature range. The light induced cis–trans

  通过简单直接的合成方法，合成了以强极性的氰基和硝基部分为取代基，另一端为烷氧基（丁基至十二烷基）为取代基的非手性不对称四环弯曲核液晶。四个苯环分别通过偶氮，酯和亚胺键连接，并且弯曲单元衍生自在分子的横向方向上具有2-甲基取代基的3-氨基苯甲酸。分子结构表征与元素和光谱分析数据一致。通过差示扫描量热法和偏振光学显微镜研究了材料的热行为和相表征。所有化合物在较宽的温度范围内均表现出对映向列相。光诱导顺反式 还讨论了异构化。
• Development of nematic and orthogonal smectic phases in short-core fluorinated hockey-stick shaped liquid crystal compounds
  作者：Kalpana Upadhyaya、Sharmistha Ghosh、Raj Kumar Khan、R. Pratibha、Nandiraju V.S. Rao

  DOI：10.1016/j.molliq.2019.111989

  日期：2020.1

  Here we report synthesis and investigations on novel short-core hockey-stick shaped molecules bearing a 4-n-alkyloxy-2-hydroxybenzylidene moiety at one end and polar fluoro-biphenyl moiety at the other end. The polar chloro and fluoro substituent at the lateral position of the core confers nematic and orthogonal smectic mesomorphism. The mesophase morphology is characterized by polarizing optical microscopy

  在这里我们报告合成和研究新型短核曲棍球棒状分子，一端带有4-n-烷氧基-2-羟基亚苄基部分，而另一端带有极性氟联苯部分。在核的侧向位置上的极性氯和氟取代基赋予向列和正交近晶同晶型。中间相形态的特征在于偏振光学显微镜（POM），差示扫描量热法（DSC），X射线衍射（XRD），电光研究和介电谱。氟化化合物1b（n = 16）和1c（n = 18）具有较长的末端烃尾，并显示具有反铁电转换行为的正交近晶相。氯化化合物2e（n = 8），具有相对较短的末端链长度，在冷却时仅表现出单向性向列相。XRD证实，向列相由柱状簇组成，并表现出电光转换。化合物2i（n = 12）表现出短距离的对映向列相和附加的正交近晶相。介电谱揭示了向列相和近晶相之间的极性相关。