4-[4-butyloxybenzylideneamino]benzoic acid | 14921-72-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-butyloxybenzylideneamino]benzoic acid
• 英文别名: p-n-Butoxybenzyliden-p-aminobenzoesaeure；4-[(4-Butoxyphenyl)methylideneamino]benzoic acid
• CAS: 14921-72-3
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: GEDPHEGFKKRRIS-UHFFFAOYSA-N

物化性质

• 沸点：
  483.1±30.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-羟基喹啉 、 4-[4-butyloxybenzylideneamino]benzoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis and mesomorphic properties of quinoline-8-yl-4-((4-n-alkoxy benzylidene) amino) benzoate: The effect of linkage group

  摘要：

  A new homologous series viz. quinoline-8-yl-4-((4-n-alkoxy benzylidene) amino) benzoate based on two central linking groups have been designed and characterised by elemental analyses and spectroscopic techniques such as Fourier transform infrared [FT-IR] and proton-magnetic resonance magnetic resonance [H-1 NMR] spectroscopy. The mesomorphic properties of these compounds were observed by polarizing optical light microscopy (POM) and confirmed by differential scanning calorimetry (DSC). All synthesized compounds displayed LC property except first two homologue. The lower homologues (n = 4 to 8) display SmA and SmC phase while, in higher homologues (n = 10 to 18) SmC and nematic phasewere seen in heating and cooling condition.

  DOI：

  10.1080/15421406.2017.1358006
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 4-[4-butyloxybenzylideneamino]benzoic acid
  参考文献：
  名称：

  席夫碱酯基同源系列中叔丁基尾基位置对液晶形成的影响

  摘要：

  图形摘要摘要我们报告了一种新的棒状光滑液晶材料，它是由基于席夫碱酯作为连接基团的棒状羧酸衍生物与叔丁基尾基团自组装构成的。合成了具有不同烷基链间隔物（n = 1 到 8、10、12、14、16 和 18）的新系列 4-（叔丁基）苯基 4-（（4-烷氧基亚苄基）氨基）苯甲酸酯及其通过差示扫描量热法和偏光显微镜研究了介晶性质。本系列中的所有同源物均以对映方式显示中间相。SmC-SmA 的热稳定性为 137.5 °C。所有化合物均通过光谱和元素分析表征。

  DOI：

  10.1080/15421406.2017.1283886

文献信息

• Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities
  作者：GuangXia Tang、JuFang Yan、Li Fan、Jin Xu、XiaoLi Song、Li Jiang、LingFei Luo、DaCheng Yang

  DOI：10.1007/s11426-012-4816-2

  日期：2013.4

  The synthesis of two series of β-amino ketones containing a p-aminobenzoic acid moiety (TM-1 and TM-2) using a modified protocol of the Mannich reaction is reported. The molecular structures of a total of tweenty three new target compounds were characterized by 1H NMR, 13C NMR, ESI-MS and HR-MS. Subsequently, their antidiabetic activities were screened in vitro. The α-glucodase inhibition (α-GI) activity of compound 1e reached a remarkable level of 66.50%. The peroxisome proliferator-activated receptor (PPAR) relative activation activities of six compounds are above 80%, and in particular 2i displays an unprecedentedly high PPAR of 130.91%. The structure-activity relationships of the compounds were established. 2i is also subject to further in-depth investigation.

  报道了使用改进的Mannich反应方案合成了包含对氨基苯甲酸部分的两种系列的β-氨基酮（TM-1和TM-2）。总共23个新目标化合物的分子结构通过1H NMR、13C NMR、ESI-MS和HR-MS进行了表征。随后，它们在体外进行了抗糖尿病活性筛选。化合物1e的α-葡萄糖苷酶抑制（α-GI）活性达到了显著的66.50%水平。六个化合物的过氧化物酶体增殖物激活受体（PPAR）相对激活活性均超过80%，其中特别是2i显示了前所未有的高PPAR值130.91%。建立了这些化合物的结构-活性关系。2i也正在进行更深入的研究。
• Synthesis of dinuclear complexes of rhenium(I) as potential metallomesogens
  作者：Marie-Andrée Guillevic、Mark E. Light、Simon J. Coles、Thomas Gelbrich、Michael B. Hursthouse、Duncan W. Bruce

  DOI：10.1039/a910273f

  日期：——

  Seven anisotropic diimines and their corresponding dinuclear complexes of rhenium(I) have been synthesized. The crystal and molecular structures of one of the dimines and two of the complexes were determined. In common with related imine ligands which have been synthesized previously, the new diimines were mesomorphic showing smectic C and nematic phases and, in some cases, smectic I and crystal J phases. However, none of the orthometallated, dinuclear complexes showed any liquid crystal phases.

  合成了7种各向异性的双亚胺及其对应的铼(I)双核配合物，测定了其中一种双亚胺及两种配合物的晶体和分子结构。与此前合成过的相关亚胺配体类似，新的双亚胺表现出介晶性，呈现近晶C相和向列相等，在某些情况下也有近晶I相和晶体J相。然而，所有形成面式金属配合物的双核配合物均未表现出任何液晶相。
• New hockey stick shaped amino allylidene (‒N˭CH‒CH˭CH) based compounds: Effect of linkage group on mesomorphic properties
  作者：Vinay. S. Sharma、Rajesh. H. Vekariya、Anuj. S. Sharma、R. B. Patel

  DOI：10.1080/15421406.2017.1357430

  日期：2017.7.24

  GRAPHICAL ABSTRACT ABSTRACT Two nonlinear hockey stick shaped homologous series based on three linking groups have been synthesized and characterized by elemental analyses and spectroscopic techniques. The mesomorphic properties of these compounds were observed by polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). In this present investigation, we have synthesized two

  图形摘要 摘要 基于三个连接基团的两个非线性曲棍球棒形同源系列已被合成并通过元素分析和光谱技术表征。通过偏光显微镜（POM）和差示扫描量热法（DSC）观察这些化合物的介晶性质。在本次调查中，我们合成了两个同源系列，即。2-((3-苯基亚丙基)氨基)苯基4-((4-n-烷氧基亚苄基)氨基)苯甲酸酯(series-1)和4-((2-((3-苯基亚丙基)氨基)苯氧基)羰基) 苯基-4-n-烷氧基苯甲酸酯（系列 2）。这两个系列在第一连接基团方面是不同的。在系列 1 中，comp.C4-C18 显示向列相和近晶相，而在系列 2 中，comp.C10-C16 显示近晶相和向列相，而 comp.C4-C18 仅显示向列相。
• Mesomorphic Behavior of Compounds Incorporating One-Unit Linking Groups. II
  作者：Y. Matsunaga

  DOI：10.1080/10587250008025235

  日期：2000.10.1

  4.4'-Bis[4(4-alkoxybenzylideneamino)benzoyloxyldiphenylmethanes bearing methoxy to decyoxy groups exhibit a smectic C phase, Compared with the behavior of the isomeric 1,4'-bis [4-(4-alkoxy-benzoyloxy)benzylideneamino]diphenylmethane, the clearing point tends to be higher though falls more rapidly by the increase of the alkyl chain length and the melting point tends to be lower, resulting in the mesophase temperature range wider by a factor of two or more for most of the homologous members. 4,4'-Bis[4-(4-alkxoybenzoyloxy)benzylideneamino]diphenylamines are nematogenic and smectic A and B phases are additionally observed for the heptyloxy and octyloxy members.
• The effect of position of <i>tert</i>-butyl tail group on the formation of liquid crystal in Schiff base ester based homologous series
  作者：V. S. Sharma、R. B. Patel

  DOI：10.1080/15421406.2017.1283886

  日期：2017.5.3

  ABSTRACT We report a newly rod like calamatic liquid crystalline materials, which are constructed by the self-organization of a rod-like carboxylic acid derivative based on Schiff base ester as the linking group with tert butyl tail group. A newly series of 4-(tert-butyl) phenyl 4-((4-alkoxybenzylidene) amino) benzoate with different alkyl chain spacer (n = 1 to 8, 10, 12, 14, 16, and 18) were synthesized

  图形摘要摘要我们报告了一种新的棒状光滑液晶材料，它是由基于席夫碱酯作为连接基团的棒状羧酸衍生物与叔丁基尾基团自组装构成的。合成了具有不同烷基链间隔物（n = 1 到 8、10、12、14、16 和 18）的新系列 4-（叔丁基）苯基 4-（（4-烷氧基亚苄基）氨基）苯甲酸酯及其通过差示扫描量热法和偏光显微镜研究了介晶性质。本系列中的所有同源物均以对映方式显示中间相。SmC-SmA 的热稳定性为 137.5 °C。所有化合物均通过光谱和元素分析表征。