cholesteryl 6-(4-nitrophenoxy)hexanoate | 1107064-47-0

• 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: cholesteryl 6-(4-nitrophenoxy)hexanoate
• 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-nitrophenoxy)hexanoate
• CAS: 1107064-47-0
• 化学式: C₃₉H₅₉NO₅
• 分子量: 621.901
• InChiKey: RXQJNVTWQWEUPV-ZWBUGVOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cholesteryl 6-(4-nitrophenoxy)hexanoate 在 copper(l) iodide 、 tetrafluoroboric acid 、 tin(II) chloride dihdyrate 、 sodium nitrite 作用下， 以 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 6-(4-(4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)phenoxy)hexanoate
  参考文献：
  名称：

  Synthesis and characterization of novel cholesterol based mesogenic compounds using ‘click’ chemistry

  摘要：

  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。

  DOI：

  10.1039/b9nj00744j
• 作为产物：
  描述：

  6-溴己酰氯 在 吡啶 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.0h， 生成 cholesteryl 6-(4-nitrophenoxy)hexanoate
  参考文献：
  名称：

  Synthesis and characterization of novel cholesterol based mesogenic compounds using ‘click’ chemistry

  摘要：

  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。

  DOI：

  10.1039/b9nj00744j

文献信息

• Highly frustrated liquid crystal phases in optically active dimers: synthesis and rich phase transitional behavior
  作者：Rashmi Ashwathama Nayak、Sachin A. Bhat、G. Shanker、D. S. Shankar Rao、C. V. Yelamaggad

  DOI：10.1039/c8nj03520b

  日期：——

  vital role in deciding the phase sequences of the dimers. In general, the dimers possessing an even-parity spacer display enantiotropic LC phases such as chiral nematic (N*), twist grain boundary (TGB), smectic A (SmA), chiral smectic C (SmC*) and twist grain boundary phase with SmC* slabs (TGBC*). Some of these dimers display TGBC* over a wide temperature range. The dimers with an odd-parity (5-oxypentanoyl)

  在本文中，我们报道了四个新的旋光性，非对称二聚体系列的合成和表征，其中胆固醇通过ω-氧烷酰基间隔基与席夫碱核心共价连接。虽然席夫碱芯取代有Ñ -butyloxy，Ñ -己氧基，Ñ -octyloxy，Ñ -decyloxy和Ñ-十二烷基氧基尾巴，三个偶数奇偶性间隔基，即4-氧丁酰基，6-氧己酸基，8-氧辛酸酰基和奇数奇偶性间隔基，即5-氧戊酰基，已被用于连接两个核。实验结果表明，间隔基的长度和奇偶性以及末端尾部的长度在决定二聚体的相序方面起着至关重要的作用。通常，具有偶数奇偶性间隔基的二聚体显示对映LC相，例如手性向列相（N *），扭曲晶界（TGB），近晶A（SmA），手性近晶C（SmC *）和扭曲晶界相，其中SmC *平板（TGBC *）。这些二聚体中的一些在较宽的温度范围内显示TGBC *。带有奇数奇偶性（5-氧戊酰基）间隔基的二聚体，与其偶数对应的蓝相（BPIII / II / I）不同；此外，它们还可以稳定N
• Observation of helical self-assembly in cyclic triphosphazene-based columnar liquid crystals bearing chiral mesogenic units
  作者：Shruti Rani、Vidhika Punjani、Santosh Prasad Gupta、Madhu Babu Kanakala、C. V. Yelamaggad、Santanu Kumar Pal

  DOI：10.1039/d2tc03847a

  日期：——

  function-integrated smart materials resulting from the spontaneous self-assembly of appropriately chosen functional molecules. Working in this direction, we have synthesized a new series of non-conventional, chiral columnar liquid crystals (Col LCs), where the cyclotriphosphazene core is surrounded by cholesterol-based Schiff base dimeric units. Cholesterol, which is covalently bound to the two-ring Schiff base

  Nowadays, intensive research has focused on the design and synthesis of function-integrated smart materials resulting from the spontaneous self-assembly of appropriately chosen functional molecules. 朝着这个方向努力，我们合成了一系列新的非常规手性柱状液晶 (Col LC)，其中环三磷腈核心被基于胆固醇的席夫碱二聚单元包围。胆固醇，通过以下方式共价结合到双环席夫碱核上一个不同长度和奇偶校验的柔性垫片，已被有预谋地结合起来，以在 Col 流体宏观结构中诱导手性。这些研究使用多种互补技术，清楚地揭示了间隔物的长度而不是奇偶性对由合成化合物的固有 Col 组装产生的 2D 晶格对称性的影响。通过详细的电子密度映射和小角/广角
• 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 Tetramers
  作者：K. C. Majumdar、S. Ponra、S. Chakravorty

  DOI：10.1080/15421406.2010.504628

  日期：2010.10.14

  Novel symmetrical liquid-crystal tetramers were designed and synthesized. The length of the central spacer and the outer spacers has been varied. The molecular structures of the target compounds were confirmed by Fourier transform infrared and proton nuclear magnetic resonance spectroscopy. The thermal phase behavior of the tetramers was investigated by polarizing optical microscopy and differential scanning calorimetry. All of the liquid-crystal tetramers showed either a chiral nematic mesophase or chiral nematic and smectic mesophases.
• Room temperature helical fluids in single-component systems
  作者：G. Shanker、A. Bindushree、K. Chaithra、P. Pratap、Ravindra Kumar Gupta、A.S. Achalkumar、C.V. Yelamaggad

  DOI：10.1016/j.molliq.2018.11.081

  日期：2019.2

  Technologically significant chiral nematic (N*) phase is a helicoidal superstructure, that is generally formed by the spontaneous self-assembly of entire chiral mesogens (mostly calamitics) or by the LC mixtures where a chiral dopant is being added to the host nematic (N) phase. However, the stabilization of the N* phase at room temperature solely by chiral mesogens is highly challenging where the molecular designing is rather crucial, and thus scarcely reported. Working in this direction, we have rationally designed, synthesized and characterized new chiral materials namely, non-symmetric dimers derived from cholesterol. Notably, as expected, some of these dimers exhibit room temperature N* phase over a wide thermal range. The exclusive occurrence of N* phase has been evidenced unequivocally with the help of polarized optical microscopy (POM) and differential scanning calorimeter (DSC). The chiroptical property of the phase has been studied by recording circular dichroism (CD) spectra as a function of temperature where the intense bisignate bands (change of sign within the band) were observed. Notably, one of the dimers forms stable gel in an aprotic solvent such as hexadecane. Thus, our study reveals a new molecular architecture to stabilize the technologically important N* phase at ambient temperature. (C) 2018 Elsevier B.V. All rights reserved.