6-(4-Formyl-phenoxy)-hexanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 250210-28-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-(4-Formyl-phenoxy)-hexanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 6-(4-formylphenoxy)hexanoate
• CAS: 250210-28-7
• 化学式: C₄₀H₆₀O₄
• 分子量: 604.914
• InChiKey: DDHRCOQOIYSMRD-BJLGNOSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  6-(4-Formyl-phenoxy)-hexanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 、 5-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以96%的产率得到[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 6-[4-[(1,3-dimethyl-2,4-dioxopyrimidin-5-yl)iminomethyl]phenoxy]hexanoate
  参考文献：
  名称：

  Synthesis and mesomorphic behaviour of new mesogenic compounds possessing a cholesteryl ester moiety connected to a pyrimidine core

  摘要：

  New mesogenic compounds containing, a cholesteryl ester and a pyrimidine moiety connected through a polymethylene spacer have been prepared. The mode of linkage has been made via -C=C- and -C=N- to undelstand the structure-property relationship. Only two compounds with a pentamethylene spacer show mesomorphic behaviour. The mesomorphic behaviour has been investigated by polarizing optical microscopy, differential scanning calorimetry and HRXRD studies. Enantiotropic smectic A, twist grain boundary (TGB), and chiral nematic mesophases are exhibited by the newly synthesized compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.065
• 作为产物：
  描述：

  6-溴己酰氯 在 吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 12.0h， 生成 6-(4-Formyl-phenoxy)-hexanoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  具有异常奇偶效应的发光手性向列二聚体。

  摘要：

  在这份报告中，基于对热和光物理性质的广泛研究得出的结果，揭示了属于两个不同系列的光致发光，手性向列（N *）液晶二聚体的异常介晶行为。它们由胆固醇和荧光三环席夫碱或水杨醛亚胺核心组成，它们通过长度和奇偶性不同的ω-氧链烷酰氧基间隔基相互连接。通过改变末端n的长度来探究分子结构对两个系列的液晶（LC）行为和光物理性质的影响。用于固定（奇数或偶数）间隔基的烷氧基尾基。使用补充技术进行的详细研究不仅证明了所有合成的二聚体中都存在N *相，而且还出现了令人着迷的奇偶效应。包含偶数间隔基的所有二聚体中都存在蓝相（BP），令人惊讶的是，它们的奇数间隔基中完全不存在蓝相。尽管迄今为止报道的结果与上述发现完全相反，但这种非典型行为是根据末端尾部的取向所呈现的二聚体的整体形状来解释的。进行的光物理研究清楚地揭示了二聚体的内在发光特征，不仅在其稀溶液中，而且在它们的三个凝聚态，即固态，N *相和各向同性液态；正如预期的那样，N

  DOI：

  10.1002/cphc.201900716

文献信息

• Chiral liquid crystal tetramers
  作者：Toby Donaldson、Peter A. Henderson、Marie France Achard、Corrie T. Imrie

  DOI：10.1039/c1jm10992h

  日期：——

  The synthesis and characterisation of two new series of liquid crystal tetramers in which four mesogenic groups are linked via three alkyl spacers is reported. In each series the length of the outer two spacers, n, is varied between 3, 4, 5, 7, 10 and 11 methylene units while the central spacer length, m, is either 5 or 6 methylene units. The outer two mesogenic groups are cholesteryl-based, Chol, while the inner two are Schiff's bases, SB. The tetramers are referred to by the acronym Chol-n-SB-m-SB-n-Chol. All twelve tetramers exhibit an enantiotropic chiral nematic phase. The chiral nematic-isotropic transition temperatures and associated entropy changes depend critically on the combination of spacers in the tetramer and this is interpreted in terms of average molecular shapes. The tetramers with m = 5 and n = 5, 7, and m = 6 and n = 3, 4, 5, 7, show a monolayer chiral smectic C* phase, the driving force for which may be the mismatch in the cross-sectional areas of the differing mesogenic groups. The tetramers with m=6 and n = 10, 11 show a quadruply intercalated smectic A phase characterised by a smectic periodicity to estimated molecular length ratio of just 0.23. The driving force for the formation of this phase is thought to be specific electrostatic interactions between the unlike mesogenic units while the formation of the phase is strongly dependent on the length and parity of the spacers due to packing constraints. On cooling, a new phase transition is seen, possibly driven by conformational changes in the outer flexible spacers, for both these tetramers from the intercalated smectic A phase to an intercalated alternating chiral smectic C* phase in which the layers consist of either the mixed mesogenic groups or solely the cholesteryl-based moieties.

  报道了两种新型液晶四聚体的合成和表征，其中四个介晶基团通过三个烷基间隔基连接。在每一系列中，外部两个间隔基的长度n在3、4、5、7、10和11个亚甲基单元之间变化，而中央间隔基的长度m为5或6个亚甲基单元。外部的两个介晶基团是胆固醇基的，记为Chol，而内部的两个是席夫碱，记为SB。这些四聚体用缩写Chol-n-SB-m-SB-n-Chol表示。所有十二个四聚体都表现出手性向列相的性质。手性向列相-各向同性相的转变温度及其相关的熵变化关键取决于四聚体中间隔基的组合，这可以通过平均分子形状来解释。具有m=5和n=5、7以及m=6和n=3、4、5、7的四聚体显示出单层手性近晶C*相，其形成的驱动力可能是不同介晶基团横截面积的不匹配。具有m=6和n=10、11的四聚体显示出四重交错排列的近晶A相，其特征是近晶层周期与估计分子长度之比仅为0.23。该相形成的驱动力被认为是不同介晶单元之间的特定静电相互作用，而相的形成强烈依赖于间隔基的长度和奇偶性，这是由于堆积限制。在冷却过程中，对于这两个四聚体，从交错排列的近晶A相到交错排列的交替手性近晶C*相，出现了一个新的相变，这种相变可能是由外部柔性间隔基的构象变化驱动的，其中层由混合介晶基团或仅由胆固醇基部分组成。
• Synthesis and characterization of novel cholesterol based mesogenic compounds using ‘click’ chemistry
  作者：K. C. Majumdar、Shovan Mondal、Randhir K. Sinha

  DOI：10.1039/b9nj00744j

  日期：——

  An efficient route for the synthesis of hitherto unreported non-symmetric dimesogens consisting of a cholesteryl moiety and an aromatic mesogenic unit interconnected through a pentamethylene or decamethylene spacer by Cu(I)-catalyzed azide–alkyne cycloaddition ‘click’ chemistry has been developed. The aromatic units consist of two phenyl rings linked to a triazole moiety. A new trimesogen consisting two cholesteryl esters and an aromatic segment joined by pentamethylene spacer has also been synthesized. The newly synthesized mesogens show N*, TGB and partially bilayered SmC* (SmCd*) phases. The liquid crystalline phases were investigated with the help of polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and powder X-ray diffraction studies. DFT study was also used to locate the orientation of the dipole at the centre position i.e. at ester linkage. All the compounds were characterized from their elemental analyses and spectral data.

  一种合成至今未报道的不对称二聚液晶的新颖高效路线已经通过铜(I)催化的叠氮-炔环加成“点击”化学反应被开发出来，该路线结合了一个胆甾基团和一个芳香性介晶单元，通过戊二基或癸二基间隔基相连。芳香单元由两个苯环与一个三唑基团相连构成。一种含有两个胆甾基酯和一个芳香段通过戊二基间隔基连接的新型三聚液晶也被合成。新合成的液晶显示出了N*相、TGB相以及部分双层结构的SmC* (SmCd*)相。这些液晶的液态晶相性质在偏光显微镜(POM)、差示扫描量热法(DSC)以及粉末X射线衍射研究的帮助下进行了探究。密度泛函理论(DFT)研究也被用于确定中心位置即酯键合处的偶极取向。所有化合物均通过其元素分析和光谱数据进行了表征。
• Glass-forming organic radical compounds with cholesterol and benzylideneamine cores
  作者：Hidetoshi Kinoshita、Masayuki Hata、Ammathnadu S. Achalkumar、Channabasaveswar V. Yelamaggad、Hiroki Akutsu、Jun-ichi Yamada、Shin’ichi Nakatsuji

  DOI：10.1016/j.tetlet.2005.07.132

  日期：2005.9

  Several organic radical compounds based on TEMPO radical with cholesterol and benzylideneamine cores (3a-C) were prepared. The radical compounds were found to freeze into glassy state when cooled from their isotropic liquid state and characteristic heat-responsive magnetic properties were observed in the radicals due to the phase transitions. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and thermal behavior of chiral oligomers derived from cholesterol
  作者：K.C. Majumdar、S. Chakravorty、N. Pal、Nandiraju V.S. Rao

  DOI：10.1016/j.tet.2008.10.085

  日期：2009.1

  Synthesis and thermal properties of a series of Schiff base oligomers derived from naturally occurring cholesterol are described. In particular, four of them show smectic A and/or chiral nematic phase/s or an unknown mesophase, while the other is non-mesomorphic. Molecular packing in the SmA phase has been determined by the HRXRD experiment. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of cholesterol-based nonsymmetric dimers terminated with ferrocenyl core
  作者：K.C. Majumdar、Santanu Chakravorty、Nilashish Pal、Randhir K. Sinha

  DOI：10.1016/j.tet.2009.07.042

  日期：2009.9

  The molecular design, synthesis, and thermal behavior of cholesterol-based nonsymmetric dimers, which can also be regarded as metallomesogens, consisting of either two- or three-ring aromatic cores terminated with ferrocenyl unit are reported. The spacer length connecting the cholesterol and aromatic cores is held constant while the length of the spacer connecting ferrocene and aromatic cores has been varied. The occurrence of the enantiotropic mesomorphism in these compounds has been adjudged by optical, calorimetric, and X-ray diffraction studies. In particular these systems exhibit liquid crystal phases Such as chiral nematic, twist grain boundary, and smectic A phases. Of these, the chiral nematic phase commonly occurs in all the synthesized compounds. (C) 2009 Elsevier Ltd. All rights reserved.