1-(cholest-5-en-3β-yloxy)pentan-5-ol | 335196-18-4

• 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: 1-(cholest-5-en-3β-yloxy)pentan-5-ol
• 英文别名: cholest-5-en-3β-oxy-pentan-5-ol；5-cholesteryloxypentanol
• CAS: 335196-18-4
• 化学式: C₃₂H₅₆O₂
• 分子量: 472.795
• InChiKey: HUBVGJOBRLTIFZ-RWFZIKKDSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  556.0±43.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.58
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(cholest-5-en-3β-yloxy)pentan-5-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以97%的产率得到cholest-5-en-3β-oxy-5-bromopentane
  参考文献：
  名称：

  Structure of cholest-5-en-3β-oxy-5-bromopentane by single-crystal X-ray diffraction at 130 K

  摘要：

  Cholest-5-en-3 beta -oxy-5-bromopentane (1) and cholest-5-en-3 beta -oxy-11-bromoundecane (2), key precursors for the synthesis of novel cationic amphiphiles based on cholesterol, have been synthesized and characterized by H-1-NMR spectroscopy and X-ray crystallography. Thermal disorder and effect of length of the bromoalkyl segment on the crystal structure have been investigated. Possible molecular level explanation of the unusual alternating s-trans-gauche conformation of the bromopentyl side chain of (Ij has been presented. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(00)00823-1
• 作为产物：
  描述：

  胆固醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(cholest-5-en-3β-yloxy)pentan-5-ol
  参考文献：
  名称：

  Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths

  摘要：

  一系列具有不同间隔的偶氮苯 - 胆固醇有机凝胶化合物（M0-M12）被设计并合成。分子结构经过1H NMR和13C NMR光谱确认。通过UV-vis光谱研究了化合物的快速可逆光响应特性。它们的热相行为通过DSC进行了研究。间隔物的长度在凝胶化中起着至关重要的作用。化合物M6是唯一能在乙醇、异丙醇和1-丁醇中凝胶化的化合物，其可逆凝胶-溶胶转变也得到了研究。为了获得对凝胶微观结构的视觉洞察，通过SEM研究了干凝胶的典型结构。聚集体的形态从花状、网络状到不同尺寸的棒状发生变化。通过IR和XRD表征，发现分子间氢键、溶剂和范德华相互作用是特定超结构的主要贡献。

  DOI：

  10.3762/bjoc.11.122

文献信息

• Liquid Crystals Derived from Hydrogen-Bonded Supramolecular Complexes of Pyridinylated Hyperbranched Polyglycerol and Cholesterol-Based Carboxylic Acids
  作者：Theodoros Felekis、Leto Tziveleka、Dimitris Tsiourvas、Constantinos M. Paleos

  DOI：10.1021/ma047958p

  日期：2005.3.1

  A hyperbranched polyether polyol was reacted with isonicotinoyl chloride hydrochloride for the introduction of the pyridinyl moiety at the external surface. This pyridinylated hyperbranched polymer was subsequently interacted with cholesterol-based carboxylic acids for the formation of the corresponding hydrogen-bonded supramolecular complexes. The materials obtained exhibited smectic A liquid crystalline phases over a broad thermal range from room temperature up to above 170degreesC. Within this smectic layer the cholesterol moieties are located above and below the hyperbranched scaffold. Increasing the spacer length, located between the carboxylic group and the cholesterol moiety, the temperature range of the liquid crystalline phases of the complexes is lowered.
• Tailoring Crystallization Behavior of PEO-Based Liquid Crystalline Block Copolymers through Variation in Liquid Crystalline Content
  作者：Yuxiang Zhou、Suk-kyun Ahn、Rubinder Kaur Lakhman、Manesh Gopinadhan、Chinedum O. Osuji、Rajeswari M. Kasi

  DOI：10.1021/ma102922u

  日期：2011.5.24

  A series of liquid crystalline-semicrystalline-liquid crystalline triblock copolymers, with poly(ethylene oxide) (PEO) as the semicrystalline central block and polymethacrylate bearing side-chain cholesteryl mesogens as the liquid crystalline (LC) end blocks, are prepared using reversible addition fragmentation chain transfer (RAFT) polymerization. Starting with 20 kg/mol PEO, the weight fractions of the LC blocks in the triblock copolymers are varied from 21 to 86 wt %. The wide-angle and small-angle X-ray scattering (WAXS and SAXS) as well as transmission electron microscopy (TEM) studies show that with the increased LC content in the triblock copolymers different hierarchical structures including "LC lamellae in PEO lamellae" and "PEO cylinders in LC matrix" are observed sequentially. Differential scanning calorimetry (DSC) study shows that the triblock copolymers with "LC lamellae in PEO lamellae" crystallize at normal undercooling conditions (crystallization temperature T-c observed at 31.0-36.4 degrees C, which is close to that of homopolymer PEO), while those with "PEO cylinders in LC matrix" crystallize at very large undercooling (T-c drops to -23.5 to -27.8 degrees C). The large variation of the undercooling conditions required for PEO crystallization is attributed to the nanoconfinement effect from different hierarchical structures at varied LC contents. Avrami analysis has been performed to understand the PEO crystallization mechanism. In "LC lamellae in PEO lamellae", the PEO crystallization is confined within 2D microdomains between LC lamellae and follows heterogeneous nucleation mechanism with subsequent long-range crystal growth. In "PEO cylinders in LC matrix", the PEO crystallization is confined within ID cylindrical microdomains and dominated by homogeneous nucleation, and long-range crystal growth is prohibited by the surrounding LC matrix. This study demonstrates that microsegregated LC domains can provide efficient confinement of the PEO crystallization, and by simply increasing the LC content, amorphous PEO can be obtained at room temperature. These LC-semicrystalline-LC triblock copolymers, with room temperature amorphous PEO confined in microsegregated nanodomains, may be used as scaffolds for lithium ion batteries and solid-state electrolytes.