cholesteryl 11-bromoundecanoate | 82962-34-3

• 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 11-bromoundecanoate
• 英文别名: Cholest-5-en-3-ol (3beta)-, 3-(11-bromoundecanoate)；[(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] 11-bromoundecanoate
• CAS: 82962-34-3
• 化学式: C₃₈H₆₅BrO₂
• 分子量: 633.837
• InChiKey: DIPGSHTZYTZXEJ-HMVYLTCSSA-N

物化性质

• 熔点：
  95 °C(Solv: ethanol (64-17-5))
• 沸点：
  634.6±38.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cholesteryl 11-bromoundecanoate 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 24.5h， 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 11-(4-((1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)phenoxy)undecanoate
  参考文献：
  名称：

  具有连接到嘧啶核的胆固醇部分的新型棒状液晶二甲基原的合成和介晶行为

  摘要：

  通过钯介导的 Sonogashira 交叉偶联制备了由胆固醇部分和通过五亚甲基或十亚甲基间隔互连的嘧啶单元组成的新型非对称 dimesogens。新型介晶仅显示手性向列相。通过偏振光学显微镜和差示扫描量热法研究液晶相。所有化合物均通过元素分析和光谱数据进行表征。

  DOI：

  10.1080/15421406.2013.779180
• 作为产物：
  描述：

  11-溴十一酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 cholesteryl 11-bromoundecanoate
  参考文献：
  名称：

  Nakamura, Naotake; Hanasaki, Tomonori; Onoi, Hidekazu, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 225, p. 269 - 278

  摘要：

  DOI：

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 mesomorphic behaviour of new discotic liquid crystalline compounds containing triphenylamine as a core moiety via Sonogashira coupling
  作者：K.C. Majumdar、Shovan Mondal、Nirupam De、Randhir Kumar Sinha、Nilasish Pal、B. Roy

  DOI：10.1016/j.tetlet.2009.11.066

  日期：2010.1

  Design and synthesis of cholesterol based disk-like liquid crystalline compounds using triphenylamine as a core moiety have been achieved by Pd-catalyzed cross-coupling reaction. The newly synthesized compounds exhibit a cholesteric phase with fingerprint texture as well as oily texture. In the low temperature region, there is a signature of smectic B with characteristic dendritic and mosaic textures

  以三苯胺为核心部分的胆固醇基盘状液晶化合物的设计和合成已通过钯催化的交叉偶联反应得以实现。新合成的化合物显示出胆甾相，具有指纹质地以及油性质地。在低温区域，近晶B具有特征性的树突和镶嵌纹理。通过偏光显微镜，差示扫描量热法和HRXRD研究表征了介晶性质。
• Heterobifunctional poly(ε-caprolactone): Synthesis of α-cholesterol-ω-pyrene PCL via combination of ring-opening polymerization and “click” chemistry
  作者：Sevinc Ilkar Erdagi、Erdinc Doganci、Cavit Uyanik、Faruk Yilmaz

  DOI：10.1016/j.reactfunctpolym.2015.12.005

  日期：2016.2

  Abstract A well-defined novel α -cholesterol and ω -pyrene heterobifunctional poly(e-caprolactone) (Chol-PCL-Pyr) was synthesized by a combination of ring-opening polymerization (ROP) and “click” chemistry techniques. A cholesterol compound with hydroxyl functional group was used as the initiator in the ROP of e-caprolactone (e-CL) to prepare α -cholesterol- ω -hydroxy PCL polymer (Chol-PCL-OH). ω

  摘要结合开环聚合（ROP）和“点击”化学技术，合成了定义明确的新型α-胆固醇和ω-py异双功能聚（ε-己内酯）（Chol-PCL-Pyr）。在ε-己内酯（e-CL）的ROP中使用具有羟基官能团的胆固醇化合物作为引发剂来制备α-胆固醇-ω-羟基PCL聚合物（Chol-PCL-OH）。然后将Chol-PCL-OH的ω-羟基官能团成功转化为溴化物和叠氮化物。ω-叠氮化物聚己内酯（Chol-PCL-N 3）的进一步端基修饰是通过铜（I）催化的叠氮化物官能团和1-乙炔基cyclo的环加成反应定量完成的，从而得到了所需的PCL具有α-胆固醇和ω-py基团（Chol-PCL-Pyr）。
• Unveiling the influence of inner spacer length of the non-linear S-shaped chiral oligomers on liquid crystalline phase
  作者：Guan-Yeow Yeap、Faridah Osman、Nobuyuki Maeta、Masato M. Ito、Chien-Min Lin、Hong-Cheu Lin

  DOI：10.1016/j.molliq.2017.03.093

  日期：2017.6

  of carbon atom at the inner spacer affects the stability of liquid crystalline phase. The homologues with shorter inner spacers n = 4 and 5 exhibit monotropic N* whilst the analogue with medium spacer n = 6 exhibits monotropic N* and SmC* phase. However, the oligomers with longer spacers n = 7, 8 and 9 exhibit enantiotropic N* and SmC* phase. The I-N* transition temperatures were found to depend on the

  合成并表征了由联苯，邻苯二酚和胆固醇部分组成的一系列S形液晶低聚物。该系列的成员之间的区别在于内部间隔基–（CH 2）n-的长度，其中n在4到9之间变化，而十一烷酸酯链的外部间隔基则保持完整。记录织构和相变温度以及相关的焓变。内部间隔物上碳原子数目的增加影响液晶相的稳定性。内部间隔物n  = 4和5较短的同系物表现出单向性N *，而中等间隔物n  = 6的类似物表现出单向性N *和SmC *相。然而，更长的间隔基寡聚物ñ = 7、8和9表现出对映N *和SmC *相。发现IN *转变温度取决于内部间隔物的奇偶性。X射线衍射研究表明S形低聚物以单层手性近晶C相存在。
• Synthesis, characterization and molecular organization for induced smectic phase of triazole ring in non-symmetric liquid crystalline dimer
  作者：Guan-Yeow Yeap、Arwa Alshargabi、Wan Ahmad Kamil Mahmood、Chun-Chieh Han、Hong-Cheu Lin、Minoru Santo、Masato M. Ito

  DOI：10.1016/j.tet.2015.04.036

  日期：2015.6

  New non-symmetric liquid crystal dimers containing cholesterol, triazole and biphenylene segments have been synthesized via click reaction. Increase in the flexible spacers length affects the mesophase formation. The homologues with short and medium alkyl spacer exhibit SmA* and SmC* phases whilst the analogue with the longest spacer favors the formation of enantiotropic SmA and N* phases. The XRD

  通过点击反应合成了含有胆固醇，三唑和联亚苯基的新型非对称液晶二聚体。柔性间隔物长度的增加影响中间相的形成。具有短和中等烷基间隔基的同系物表现出SmA *和SmC *相，而具有最长间隔基的类似物则有利于对映SmA和N *相的形成。XRD研究揭示了SmA *和SmC *相的出现，这些相可能与这些二聚体的单层排列有关。通过比较研究的进一步研究表明，三唑环影响中间相的形成，其中除分子偶极子外，微妙的静电相互作用和范德华力增强了SmC *相。