4-(4`-undecylhydroxybenzoylhydroxy)benzaldehyde | 140675-10-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(4`-undecylhydroxybenzoylhydroxy)benzaldehyde
• 英文别名: (4-Formylphenyl) 4-undecoxybenzoate
• CAS: 140675-10-1
• 化学式: C₂₅H₃₂O₄
• 分子量: 396.527
• InChiKey: UVAZESMAFIFZFI-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  537.8±35.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  4-(4`-undecylhydroxybenzoylhydroxy)benzaldehyde 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 4-(4-Undecoxybenzoyl)oxybenzoic acid
  参考文献：
  名称：

  Symmetric bent-core mesogens with m-carborane and adamantane as the central units

  摘要：

  研究人员合成了两个同源系列的对称弯曲形化合物，其中心位置为间碳酸硼烷或金刚烷（1[n]或 2[n]，n = 9-13），并采用光学、量热、X 射线衍射和电光方法对这些化合物进行了研究。结果表明，间碳硼烷系列中最短的两个成员 1[9] 和 1[10] 呈现出夹层片状 B6 相。金刚烷衍生物 2[9]-2[13] 则显示出单向性的弱双折射软结晶或结晶相，具有同手性结构域。这两种相在电场中都不会发生极化转换。

  DOI：

  10.1039/b719629f
• 作为产物：
  描述：

  过氧化氢酶 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 生成 4-(4`-undecylhydroxybenzoylhydroxy)benzaldehyde
  参考文献：
  名称：

  A New Way to Access Chiral Liquid Crystals: Organocatalyst-Mediated Synthesis of Chiral Rod-Like Liquid Crystals

  摘要：

  In this article, an asymmetric organocatalytic way to prepare chiral liquid crystals from non-chiral starting materials was described. By using L-proline as the organocatalyst, several new chiral rod-like liquid crystals that are elusive with traditional methods were prepared. In addition, a series of novel enone-containing rod-like liquid crystals were also obtained as side-products. Mesomorphic properties of all new compounds were studied by Polarized Optical Microscope and Differential Scanning Calorimetry.

  DOI：

  10.1080/15421406.2011.570138

文献信息

• Optically active, three-ring calamitic liquid crystals: the occurrence of frustrated, helical and polar fluid mesophases
  作者：B. N. Veerabhadraswamy、D. S. Shankar Rao、S. Krishna Prasad、C. V. Yelamaggad

  DOI：10.1039/c4nj02011a

  日期：——

  mesophases such as the blue phase-I/II (BPI or BPII) and chiral nematic (N*) and chiral smectic C (SmC*) phases has been evidenced unequivocally with the help of polarizing microscopy, differential scanning calorimetry, X-ray diffraction and electrical switching. Besides, the occurrence of an unknown, metastable smectic (SmX) phase below the SmC* phase has been noted. This study shows that the length of

  在此，我们报道了五个（R）-4-[（（4-（辛烷-2-基氧基）苯基）亚氨基]甲基}苯基4-（n-烷氧基）的合成，表征，液晶行为和旋光特性。苯甲酸酯及其对映体，即（S）-4-[（（4-（辛烷-2-基氧基）苯基）亚氨基]甲基]甲基4-苯基（正烷氧基）苯甲酸酯。这些三环棒状介晶是通过（R）-/（S）-4-（辛烷-2-基氧基）苯胺与4-甲酰基苯基4-（正烷氧基）苯甲酸酯的酸催化缩合制备的。因此，每对对映异构体包含（R）-2-辛氧基和（S）-2-辛氧基手性尾巴。为了理解结构与属性的关系，在另一端结合的链烷烃链的长度已从正辛氧基变为正构烷氧基。-十二烷氧基。通过几种互补技术进行的详细研究揭示了液晶相的稳定性，这在应用科学中，尤其是在各种设备应用中，具有广阔的前景。特别是在偏光显微镜，差示扫描技术的帮助下，已经明确证明了中间相的出现，例如蓝色相I / II（BPI或BPII）和手性向列相（N *）和手性近晶C（SmC
• Ferroelectric Liquid Crystals: Synthesis and Thermal Behavior of Optically Active, Three-Ring Schiff Bases and Salicylaldimines
  作者：Bhyranalyar N. Veerabhadraswamy、Doddamane S. Shankar Rao、Channabasaveshwar V. Yelamaggad

  DOI：10.1002/asia.201800119

  日期：2018.4.16

  center in the other isomer as they are derived from (3 S)‐3,7‐dimethyloctyloxy and (3 R)‐3,7‐dimethyloctyloxy tails. To probe the structure–property correlations in each series, the length of the n‐alkoxy tail situated at the other end of the mesogens has been varied from n‐octyloxy to n‐dodecyloxy. The measurement of optical activity of these chiral mesogens was carried out by recording their specific

  具有螺旋上层结构特征的手性铁电层列C（SmC *）相已被广泛用于开发高分辨率微显示器，该显示器已被有效地用于制造各种便携式设备。尽管已经设计和合成了绝大多数具有SmC *相的旋光（手性）液晶（LC），但对新系统的搜索仍在继续，以实现能够满足最终用途技术要求和规格的液晶元。在此方向上我们的研究工作继续进行，在此我们报告了属于四个系列的二十种新的光学活性三环钙钛矿型液相色谱的设计，合成和热行为。前两个系列包括五对对映体席夫碱，而其他两个系列由五对对映体水杨醛亚胺组成。在每对光学异构体中，一个立体异构体中的手性中心构型与另一种异构体中的类似中心构型相反，因为它们衍生自（3 S）-3,7-二甲基辛氧基尾巴和（3  R）-3,7-二甲基辛氧基尾巴。为了探查每个系列中的结构与性质的相关性，位于介晶另一端的正烷氧基尾巴的长度已从正辛氧基变为正构烷氧基。十二烷氧基 这些手性液晶元的旋光性的测量是通过记录它
• Synthesis and comparative study on phase transition behavior of triazole-cored liquid crystals armed with cholesterol and double or triple aromatic rings systems
  作者：Guan-Yeow Yeap、Subramanian Balamurugan、Murugesan Vijay Srinivasan、Palaninathan Kannan

  DOI：10.1039/c3nj00053b

  日期：——

  Two homologous series of optically active bent-shaped mesogens comprising a cholesterol unit as one of the side arms connected to a 1,2,3-triazole ring while the other arm of the triazole ring is connected to two- and three-ring aromatic systems with varying terminal chain lengths have been synthesized. The molecular structure, thermal and optical activities have been studied extensively in which the compounds from both series exhibit polymorphism ranging from chiral nematic (N*), chiral smectic A (SmA*), chiral smectic C (SmC*) and twist grain boundary (TGBC*) phases. A further comparison between the two series of target compounds has drawn a common remark of which the phase behavior is found to be dependent on the length of the terminal tail and number of aromatic rings in the mesogenic units.

  我们合成了两个同源系列的具有光学活性的弯曲状中间体，其中一个侧臂由胆固醇单元组成，与 1,2,3 三唑环相连，而三唑环的另一个侧臂则与具有不同末端链长度的二环和三环芳香系统相连。我们对这两个系列的化合物的分子结构、热学和光学活性进行了广泛研究，发现它们具有手性向列相 (N*)、手性 Smectic A 相 (SmA*)、手性 Smectic C 相 (SmC*) 和扭曲晶界相 (TGBC*) 等多态性。通过对这两个系列的目标化合物进行进一步比较，我们发现了一个共同点，即相行为取决于末端尾部的长度和中生单元中芳香环的数量。
• Liquid Crystalline Properties of 3-[4-(4′-Alkoxybenzoyloxybenzylidene) amino]-1,2,4-triazines: Synthesis and Characterization
  作者：Bachcha Singh、Ashwini Pandey、Sachin Kumar Singh

  DOI：10.1080/15421400903483957

  日期：2010.2.25

  A new series of 3-[4-(4′-alkoxybenzoyloxybenzylidene)amino]-1,2,4-triazines, C3H2N3N˭CHC6H4OCOC6H4OCmH2m + 1 where m = 6, 7, 8, 9, 10, 11, 12, 14, and 16 have been synthesized. These compounds have been characterized by elemental analyses, FT-IR, UV-visible, 1H, and 13C NMR spectroscopy. Mesomorphic properties of these compounds were studied by differential scanning calorimetry and polarizing microscopy

  新系列的 3-[4-(4'-烷氧基苯甲酰氧基亚苄基)氨基]-1,2,4-三嗪，C3H2N3N˭CHC6H4OCOC6H4OCmH2m + 1 其中 m = 6, 7, 8, 9, 10, 11, 12, 14,并且合成了16个。这些化合物已通过元素分析、FT-IR、UV-可见光、1H 和 13C NMR 光谱进行表征。通过差示扫描量热法和偏光显微镜研究了这些化合物的介晶性质。这些化合物的介晶性质取决于烷氧基链长。化合物 (m = 6, 7) 不表现出介晶现象，而化合物 (m = 8, 9, 11, 12, 14) 在冷却循环中显示出单向向列中间相。3-[4-(4'-decyloxybenzoyloxybenzylidene)amino]-1,2,4-triazine 显示对映向列中间相，十六烷氧基化合物显示近晶 A 中间相。
• Synthesis of Symmetric Liquid Crystal Dimers Based on 1,2-bis{-[-(4-alkoxybenzoyloxy)benzylidene]amino)phenoxy}ethane and Investigation of Phase Behaviour by Varying Alkoxy Terminal Chain Length
  作者：Chang Sin Lee、Tae Hyeong Kim、B. Ramaraj、Seok Gn Ryu、Hyun Hoon Song、Soo-Min Lee、Kuk Ro Yoon

  DOI：10.1080/15421400802331091

  日期：2008.10.9

  With the objective to study the effect of alkoxy terminal chain length on mesomorphic properties of liquid crystals, We have synthesized ester and Schiff base dimers from diamine derivative containing 1,2-dioxyethylene as short spacer with aldehyde derivatives having different lengths of terminal alkoxy chains (n=6-12). The chemical structure of the final products was investigated by fourier transform infrared (FT-IR) spectroscopy and proton nuclear magnetic resonance (H-1 NMR) spectroscopy. The mesomorphic properties and optical textures of the resultant dimers were characterized by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). It was found that all the dimers show mesomorphic properties and the increase in terminal alkoxy chain length has pronounced effect on the mesomorphic properties. The temperature range of smectic phase window widens and nematic-isotropic phase window narrows sharply with increasing alkoxy chain length.