4-formylphenyl 4-n-dodecyloxycinnamate | 76622-48-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-formylphenyl 4-n-dodecyloxycinnamate
• 英文别名: (4-formylphenyl) 3-(4-dodecoxyphenyl)prop-2-enoate
• CAS: 76622-48-5
• 化学式: C₂₈H₃₆O₄
• 分子量: 436.591
• InChiKey: WORGVSKHHGIMMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  间苯二胺 、 4-formylphenyl 4-n-dodecyloxycinnamate 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以91%的产率得到N,N'-bis[4-(4-n-dodecyloxycinnamoyloxy)benzylidene]-1,3-phenylenediamine
  参考文献：
  名称：

  横向取代的对称和非对称水杨烯亚胺基弯曲核心介晶。

  摘要：

  弯曲核介晶由于能够形成具有不寻常特性的新中间相而获得了相当大的重要性。弯曲核分子的化学结构与形成的中间相的类型和物理性质之间的关系在细节上相对未知，并且与已知的棒状液晶的关系大不相同。本文介绍了对称和非对称的基于五环水杨基苯胺的弯曲核介晶，以及连接在外苯环 (F、Cl、Br) 或中心苯环 (CH(3)) 上的侧向取代基对研究了液晶行为和物理性质。另外制备了相应的基于亚苄基苯胺的化合物以研究分子内氢键的影响。通过差示扫描量热法、偏光显微镜、X 射线衍射和介电和电光测量来研究发生的中间相。该论文报告了关于弯曲核介晶的结构-性质关系的新发现。一方面，横向取代的卤素原子 F、Cl 和 Br 对三个异构系列的中间相行为的破坏作用远低于预期。另一方面，观察到由于小的横向取代基引起的清除温度增加了 34 K。电光行为，尤其是极性转换的类型和相应的分子运动，对分子结构的变化很敏感。该论文报告了关于弯曲核介

  DOI：

  10.3762/bjoc.8.15
• 作为产物：
  描述：

  4-正癸氧基苯甲醛 在 哌啶 、 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 25.0h， 生成 4-formylphenyl 4-n-dodecyloxycinnamate
  参考文献：
  名称：

  Synthesis, Characterization and Mesomorphic Properties of New Rod-like Thiophene Based Liquid Crystals

  摘要：

  Two new mesogenic homologous series of Schiff base esters, 2-[4-(4'-n-Alkoxy benzoyloxy) benzylidenamino] 3-cyno thiophine (Series-A) and Schiff base cinnamates, 2-[4(4'-n-alkoxy cinnamoyloxy) benzylidenamino] 3-cyano thiophene (Series-B), comprising a thiophene moiety were synthesized. Structural elucidation was carried out using elemental analysis and spectroscopic techniques such as FT-IR, H-1-NMR and C-13-NMR, and mass spectrometry. The mesomorphic properties and thermal stabilities of the title compounds were studied by using differential scanning calorimetry and optical polarizing microscopy. All the derivatives are mesomorphic in nature showing the nematic phase, and the higher members of Series-A show a smectic C phase whereas Series-B exhibits only the nematic mesophase. The mesomorphic properties of the present series are compared with other structurally related compounds.

  DOI：

  10.1080/10426507.2012.673943

文献信息

• On the balance between syn- and anticlinicity in smectic phases formed by achiral hockey-stick mesogens with and without chiral dopants
  作者：Eva Enz、Sonja Findeisen-Tandel、Roman Dabrowski、Frank Giesselmann、Wolfgang Weissflog、Ute Baumeister、Jan Lagerwall

  DOI：10.1039/b820717h

  日期：——

  A series of achiral hockey-stick-shaped mesogens forming tilted smectic liquid crystal phases of synclinic SmC- as well as anticlinic SmCa-type was prepared and characterized. While all homologues exhibit both phases, the balance shifts from anticlinic to synclinic order upon elongation of the terminal chain at the meta- position, defining the hockey-stick shape. The elongation also leads to an increased kinetic hindrance of the transition between syn- and anticlinic phases and a decreased transition enthalpy. These observations indicate that a well-defined kink (short meta-substituted chain) promotes the anticlinic structure while a higher flexibility between kinked and rod-shape (long meta-substituted chain) promotes synclinic order. An intermediate chain-length homologue was selected as host material for doping with syn- and anticlinic rod-shaped chiral dopants, respectively, at varying concentrations. Opposite of what might be expected the balance between syn- and anticlinic order was not simply dictated by the choice of dopant. Instead, both types of tilting order prevailed with roughly the same strength as in the achiral host regardless of which chiral material was added, up to concentrations well beyond normal doping conditions. Thus, at least with hockey-stick-shaped achiral hosts, syn- as well as anticlinic chiral compounds can be used effectively as chiral dopants without necessarily having an important impact on the clinicity of the resulting mixture. The hockey-stick design concept should be useful in producing achiral anticlinic-forming mesogens for low-polarization, long-pitch antiferroelectric liquid crystal mixtures. Finally, we point out that a mixture study like the one carried out here yields a conclusive means of establishing the clinicity of achiral tilted smectics, an endeavour that can sometimes be far from trivial.

  制备并表征了一系列非手性曲棍球棒状介晶，形成向斜 SmC 型和背斜 SmCa 型倾斜近晶液晶相。虽然所有同系物都表现出两个相，但在间位末端链伸长时，平衡从背斜顺序转变为向斜顺序，从而定义了曲棍球棒形状。伸长还导致顺斜相和背斜相之间转变的动力学阻碍增加以及转变焓降低。这些观察结果表明，明确的扭结（短间位取代链）促进了背斜结构，而扭结和棒状（长间位取代链）之间更高的灵活性促进了向斜有序。选择中间链长同系物作为主体材料，分别以不同浓度掺杂顺斜棒状手性掺杂剂和背斜棒状手性掺杂剂。与预期相反，顺斜序和背斜序之间的平衡并不简单地由掺杂剂的选择决定。相反，无论添加哪种手性材料，两种类型的倾斜顺序都以与非手性主体大致相同的强度为主，浓度远远超出正常掺杂条件。因此，至少对于曲棍球棒形状的非手性主体，顺斜和反斜手性化合物可以有效地用作手性掺杂剂，而不必对所得混合物的临床性产生重要影响。曲棍球棒设计概念应该可用于生产低偏振、长螺距反铁电液晶混合物的非手性反斜形成介晶。最后，我们指出，像这里进行的混合研究提供了一种确定非手性倾斜近晶临床性的决定性方法，这一努力有时可能绝非微不足道。
• Synthesis and Mesomorphic Investigations of Liquid Crystalline Compounds Having a Benzothiazole Ring
  作者：B. T. Thaker、N. J. Chothani、B. S. Patel、Y. T. Dhimmar、D. B. Solanki、Neeraj Patel、K. B. Patel、U. Makawana

  DOI：10.1080/15421406.2013.766947

  日期：2013.6.1

  Two homologous series of calamitic liquid crystals containing a benzothiazole ring and two different linkages have been prepared, and their liquid crystalline properties are studied and compared with each other and those of similar structure. The mesogens with only the cinnamate linking group showed better thermal properties than those with an ester. Nematic and smectic phases were observed. All the compounds of both the series were characterized by elemental analysis, FT-IR, mass spectrometry, H-1-NMR, and C-13-NMR. Phase transition temperatures and the thermal parameters were obtained from differential scanning calorimetery (DSC). The textural observations were performed using hot-stage Polarizing Optical Microscopy (POM).
• New Mesogenic Homologous Series of Schiff Base Cinnamates Comprising Naphthalene Moiety
  作者：A. K. Prajapati、Viral Thakkar、Nilesh Bonde

  DOI：10.1080/10587250307066

  日期：2003.1.1

  New mesogenic homologous series of Schiff base cinnamates comprising a naphthalene moiety were prepared by condensing different 4(4'-n-alkoxy cinnamoyloxy) benzaldehydes with 2-amino naphthalene. All the synthesized compounds were characterized by combination of elemental analysis and spectroscopic techniques. All the homologues synthesized exhibit mesomorphism. The mesomorphic properties of the present series are compared with other structurally related series.
• Merlo, Aloir; Gallardo, Hugo; Taylor, T. R., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 250, p. 31 - 40
  作者：Merlo, Aloir、Gallardo, Hugo、Taylor, T. R.、Kroin, Teodosio

  DOI：——

  日期：——
• Lohar, J. M.; Dhabhai, D. N., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 6, p. 536 - 537
  作者：Lohar, J. M.、Dhabhai, D. N.

  DOI：——

  日期：——