4-(dodecyloxy)-3-methoxybenzaldehyde | 93206-91-8

• 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-(dodecyloxy)-3-methoxybenzaldehyde
• 英文别名: 3-methoxy-4-dodecyloxy-benzaldehyde；4-dodecoxy-3-methoxybenzaldehyde
• CAS: 93206-91-8
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: DNOUZCXUTYVRSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(dodecyloxy)-3-methoxybenzaldehyde 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 potassium tert-butylate 、 sodium ethanolate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.5h， 生成 (3,4-bis(4-(dodecyloxy)-3-methoxyphenyl)-1H-pyrrol-2-yl)methanol
  参考文献：
  名称：

  Peripherally Fused Porphyrins via the Scholl Reaction: Synthesis, Self-Assembly, and Mesomorphism

  摘要：

  Oxidative coupling of activated aryl groups attached to beta-positions of the porphyrin ring provides convenient access to derivatives containing peripherally fused phenanthrene and benzo[g]chrysene units. Tetra(benzochryseno)porphyrin, reported here for the first time, contains a nonplanar, sterically locked pi system and shows very intense electronic absorptions in the Q range of the electronic spectrum. Tetraphenanthroporphyrins show a tendency to aggregate in solution. In one case, a discrete dimer is formed, whose structure was investigated spectroscopically and theoretically. Derivatives bearing long alkyl chains are mesomorphic and exhibit columnar phases (tetraphenanthroporphyrins) and a monoclinic 3D phase (tetrabenzochrysenoporphyrin). The symmetry of column packing in the columnar phases is dependent on the number of alkyl chains per molecule. X-ray diffraction measurements show that, in spite of their nonplanarity, the aromatic cores in the mesophases are tightly stacked within the column. The corresponding stacking patterns were derived from the structure of the dimer, on the basis of geometrical analysis and molecular modeling.

  DOI：

  10.1021/ja210991f
• 作为产物：
  描述：

  香草醛 、 溴代十二烷 生成 4-(dodecyloxy)-3-methoxybenzaldehyde
  参考文献：
  名称：

  Alkoxy substituted (E,E)-3,6-bis(styryl)pyridazine—a photosensitive mesogen for liquid crystals

  摘要：

  (E,E)-3,6-二联苯基吡喃系物(3a-t类)通过应用西格里反应制备，使用的底物是3,6-二甲基吡啶(13)和对应的亚胺4a-t或10a-t。这些变形色液态晶体相(N, S-A, S-B, S-C, S-E, S-1/F和 Cub)的交叉偶极矩导致它们展现出极强的自组织倾向，尤其是高热力学稳定性和极性。这些共轭中心结构也具有高感光性，尤其是对于(E,E)可逆逆向的(E,Z)异构转变反应，这种特性使其成为光学成像和转态切换技术中很有兴趣的研究对象。 (c) 2008 版权所有，Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.04.033

文献信息

• Synthesis, Characterization, and Mesomorphic Properties of New Pyridine Derivatives
  作者：Ahipa T. N.

  DOI：10.1002/open.201500158

  日期：2015.12

  Luminescent liquid crystals have received significant research interest due to their wide range of applications. Here, new pyridine derivatives were designed as liquid crystalline materials. They were successfully synthesized via appropriate synthetic routes, their structures confirmed by various spectral techniques, and finally characterized for their mesogenic, optical and optoelectronic properties

  发光液晶由于其广泛的应用而受到了广泛的研究兴趣。在这里，新的吡啶衍生物被设计为液晶材料。它们是通过适当的合成路线成功合成的，其结构已通过各种光谱技术证实，并最终通过介晶，光学和光电特性进行了表征。
• Dynamic Amphiphile Libraries To Screen for the “Fragrant” Delivery of siRNA into HeLa Cells and Human Primary Fibroblasts
  作者：Charlotte Gehin、Javier Montenegro、Eun-Kyoung Bang、Ana Cajaraville、Shota Takayama、Hisaaki Hirose、Shiroh Futaki、Stefan Matile、Howard Riezman

  DOI：10.1021/ja404153m

  日期：2013.6.26

  Dynamic amphiphiles are amphiphiles with dynamic covalent bridges between their hydrophilic heads and their hydrophobic tails. Their usefulness to activate ion transporters, for odorant release, and for differential sensing of odorants and perfumes, has been demonstrated recently. Here, we report that the same "fragrant" dynamic amphiphiles are ideal to screen for new siRNA transfection agents. The

  动态两亲物是在其亲水头和疏水尾之间具有动态共价桥的两亲物。最近已经证明了它们在激活离子转运蛋白、气味释放以及气味和香水的差异感应方面的有用性。在这里，我们报告相同的“香”动态两亲是筛选新的 siRNA 转染剂的理想选择。这种方法的优点包括快速访问相当大的复杂结构库，以及可能在途中进行转化以帮助吸收和最小化毒性。我们报告的单组分系统在 HeLa 细胞中 EGFP 击倒的效率和速度方面都超过了最好的市售多组分鸡尾酒。在人类原代成纤维细胞中，siRNA 介导的酶抑制从 > Lipofectamine 的 30% 至 >60% 以获得最佳效果。鉴定的结构既不能从文献中也不能从荧光囊泡的结果中预测，因此支持概念创新筛选方法的重要性。
• Vanillin and o-vanillin oligomers as models for dendrimer disassembly
  作者：Robert M. Kevwitch、Charles S. Shanahan、Dominic V. McGrath

  DOI：10.1039/c1nj20841a

  日期：——

  Linear analogs have been synthesized to model disassembling dendrimers. These linear analogs provide a facile synthesis to molecules that can be used to test new trigger groups and cleavage vectors. Vanillin and o-vanillin were used as the monomer units of these analogs and two trigger groups, allyl and o-nitrobenzyl, were chosen to test the disassembly process. Allyl triggered analogs 1a–d and 3a–d and o-nitrobenzyl triggered analogs 2a–c and 4a–c showed good to excellent disassembly as followed by the evolution of p-nitrophenoxide reporter ion by UV-Visible spectroscopy. The rate and yield of disassembly was shown to depend on experimental conditions as well as length of the cleavage vector.

  线性类似物已被合成以模拟解体的树枝状聚合物。这些线性类似物提供了一种简单的合成方法，用于制备可以测试新的触发基团和裂解向量的分子。香草醛和邻香草醛被用作这些类似物的单体单位，选择了两种触发基团：烯丙基和邻硝基苯基，以测试解体过程。烯丙基触发的类似物1a–d和3a–d，以及邻硝基苯基触发的类似物2a–c和4a–c表现出良好到优秀的解体，随着p-硝基苯氧阴离子报告离子的释放，通过紫外可见光谱进行了检测。解体的速率和产率显示出依赖于实验条件以及裂解向量的长度。
• Synthesis and characterization of new homologous series of unsymmetrical liquid crystalline compounds based on chalcones and 3, 5-disubstituted isoxazoles
  作者：SOWMYA P T、K M LOKANATHA RAI

  DOI：10.1007/s12039-016-1205-y

  日期：2017.1

  Two homologous series of unsymmetrical alkylated chalcones and 3,5-diaryl isoxazoles, consisting of 20 members, with various n-alkyl bromides (n=2−7, 10, 12, 14, 16) have been synthesized and studied for their liquid crystalline property. Simple strategy was employed to achieve the target materials. Flexibility in the synthesized molecules is provided by attaching straight alkoxy chains, where one

  合成了两个同源系列的不对称烷基化查耳酮和3,5-二芳基异恶唑（由20个成员组成）和各种正烷基溴化物（n = 2-7、10、12、14、16），并研究了它们的液晶属性。采用简单的策略来实现目标材料。通过连接直的烷氧基链来提供合成分子的柔韧性，其中一个末端基团是固定的，而另一个末端基团是变化的。基于质谱，IR和NMR光谱对合成的化合物进行表征。中间相的稳定性和范围随异恶唑上链长的增加而增加。熔点 合成了两个同源系列的不对称烷基硫族元素和3,5-二芳基异恶唑，并通过偏光显微镜（POM）和差示扫描量热法（DSC）进行了表征。
• Flavylium Salts: A Blooming Core for Bioinspired Ionic Liquid Crystals
  作者：Robert Forschner、Jakob Knelles、Korinna Bader、Carsten Müller、Wolfgang Frey、Andreas Köhn、Yann Molard、Frank Giesselmann、Sabine Laschat

  DOI：10.1002/chem.201901975

  日期：2019.10.8

  Thermotropic ionic liquid crystals based on the flavylium scaffold have been synthesized and studied for their structure‐properties relationship for the first time. The mesogens were probed by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X‐ray diffraction (XRD). Low numbers of alkoxy side chains resulted in smectic (SmA) and lamello‐columnar (LamCol) phases, whereas

  首次合成了基于flavylium支架的热致离子液晶并研究了其结构-性能关系。通过差示扫描量热法 (DSC)、偏光光学显微镜 (POM) 和 X 射线衍射 (XRD) 来探测介晶。少量烷氧基侧链导致近晶相 (SmA) 和层状柱状相 (Lam Col )，而较高取代的黄鎓盐则显示 Col ro以及有序和无序柱状 (Col ho , Col hd ) 中间相。中间相宽度范围为 13 K 至 220 K，可形成室温液晶。对合成化合物的光学性质进行了吸收和发射性质的探讨。观察到强吸收，最大值在 444 至 507 nm 之间，并且一些发色团具有高发射性，量子产率高达 99%。最终，通过固态温度依赖性发射实验检查了介晶和染料特性。