3-((3β)-cholest-5-en-3-yloxy)propanol | 77531-43-2

• 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: 3-((3β)-cholest-5-en-3-yloxy)propanol
• 英文别名: (3-cholesteryloxy)propanol；3-[[(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]oxy]propan-1-ol
• CAS: 77531-43-2
• 化学式: C₃₀H₅₂O₂
• 分子量: 444.742
• InChiKey: GOKQAWYMJDHLON-OCBUSCMESA-N

物化性质

• 沸点：
  546.4±33.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((3β)-cholest-5-en-3-yloxy)propanol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以76%的产率得到3-(cholesten-5-en-3β-yloxy)propionic acid
  参考文献：
  名称：

  Synthesis of a carborane-containing cholesterol derivative and evaluation as a potential dual agent for MRI/BNCT applications

  摘要：

  提出了一种新的双重成像和治疗剂，旨在提高硼中子俘获治疗在癌症治疗中的疗效。

  DOI：

  10.1039/c3ob42414f
• 作为产物：
  描述：

  胆固醇 在 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 1.0h， 生成 3-((3β)-cholest-5-en-3-yloxy)propanol
  参考文献：
  名称：

  Synthesis of a carborane-containing cholesterol derivative and evaluation as a potential dual agent for MRI/BNCT applications

  摘要：

  提出了一种新的双重成像和治疗剂，旨在提高硼中子俘获治疗在癌症治疗中的疗效。

  DOI：

  10.1039/c3ob42414f

文献信息

• Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths
  作者：Yuchun Ren、Bin Wang、Xiuqing Zhang

  DOI：10.3762/bjoc.11.122

  日期：——

  A series of azobenzene–cholesterol organogel compounds (M₀–M₁₂) with different spacers were designed and synthesized. The molecular structures were confirmed by ¹H NMR and ¹³C NMR spectroscopy. The rapid and reversible photoresponsive properties of the compounds were investigated by UV–vis spectroscopy. Their thermal phase behaviors were studied by DSC. The length of the spacer plays a crucial role in the gelation. Compound M₆ is the only one that can gelate in ethanol, isopropanol and 1-butanol and the reversible gel–sol transitions are also investigated. To obtain visual insight into the microstructure of the gels, the typical structures of the xerogels were studied by SEM. Morphologies of the aggregates change from flower-like, network and rod with different sizes. By using IR and XRD characterization, it is found that intermolecular H-bonding, the solvents and van der Waals interaction are the main contributions to the specific superstructure.

  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。
• ANTIMICROBIAL CATIONIC POLYCARBONATES
  申请人：CORPORATION INTERNATIONAL BUSINESS MACHINES

  公开号：US20140301968A1

  公开（公告）日：2014-10-09

  Antimicrobial cationic polymers having one or two cationic polycarbonate chains were prepared by organocatalyzed ring opening polymerization. One antimicrobial cationic polymer has a polymer chain consisting essentially of cationic carbonate repeat units linked to one or two end groups. The end groups can comprise a covalently bound form of biologically active compound such as cholesterol. Other antimicrobial cationic polymers have a random copolycarbonate chain comprising a minor mole fraction of hydrophobic repeat units bearing a covalently bound form of a vitamin E and/or vitamin D2. The cationic polymers exhibit high activity and selectivity against Gram-negative and Gram-positive microbes and fungi.

  具有一个或两个阳离子聚碳酸酯链的抗菌阳离子聚合物是通过有机催化的环氧开聚合制备的。其中一种抗菌阳离子聚合物具有基本由阳离子碳酸酯重复单元构成的聚合物链，与一个或两个末端基团相连。末端基团可以包括胆固醇等生物活性化合物的共价结合形式。其他抗菌阳离子聚合物具有随机共聚碳酸酯链，其中含有少量疏水重复单元，带有维生素E和/或维生素D2的共价结合形式。这些阳离子聚合物对革兰氏阴性和革兰氏阳性微生物和真菌表现出高活性和选择性。
• Novel methodologies for the synthesis of functionalized lipophilic carboranes
  作者：Subash C. Jonnalagadda、Steven R. Verga、Parth D. Patel、A. V. Reddy、T. Srinivas、Patricia M. Scott、Venkatram R. Mereddy

  DOI：10.1002/aoc.1598

  日期：——

  Novel synthetic protocols for the synthesis of lipophilic carboranes were developed utilizing two CC bond forming reactions, namely Baylis–Hillman and enynedioate cycloaddition reactions. Some of these carboranes were converted into further functionalized carboranes via nucleophilic allylic isomerization. Copyright © 2009 John Wiley & Sons, Ltd.

  用于亲脂性碳硼烷的合成新颖的合成方案被开发利用两个C  C键形成反应，即的Baylis-希尔曼和enynedioate环加成反应。这些碳硼烷中的一些通过亲核烯丙基异构化转化为进一步的官能化的碳硼烷。版权所有©2009 John Wiley＆Sons，Ltd.
• 10.1002/anie.202409862
  作者：Zhang, Jie、Jiao, Mengjie、Lu, Zheng、Lu, Hongjian、Wang, Minyan、Shi, Zhuangzhi

  DOI：10.1002/anie.202409862

  日期：——

  A range of d2-labeled alkanes can be synthesized via nickel-catalyzed hydrodeuterioalkylation of deuterated alkyl thianthrenium (TT) salts with unactivated alkenes. The deuterated alkyl reagents effectively integrate deuterium from D2O via pH-dependent hydrogen isotope exchange (HIE). Our method enables high deuterium incorporation and precise control over insertion site, essential for drug synthesis

  一系列 d2 标记的烷烃可以通过镍催化的氘代烷基噻啉鎓 (TT) 盐与未活化的烯烃的加氢氘烷基化来合成。氘化烷基试剂通过 pH 依赖性氢同位素交换 (HIE) 有效地整合 D 2 O 中的氘。我们的方法能够实现高氘掺入和对插入位点的精确控制，这对于药物合成至关重要。
• The synthesis of cholesterol-based cationic lipids with trimethylamine head and the effect of spacer structures on transfection efficiency
  作者：Bieong-Kil Kim、Yun-Ui Bae、Kyung-Oh Doh、Guen-Bae Hwang、Sung-Hye Lee、Hyungu Kang、Young-Bae Seu

  DOI：10.1016/j.bmcl.2011.04.071

  日期：2011.6

  Five cholesterol-based cationic lipids were newly synthesized based on cholest-5-en-3 beta-oxyethane-N,N,N-trimethylammonium bromide (Chol-ETA) structure where the cholesterol backbone is linked to cationic head via various lengths of ether-linked carbon spacer. The transfection efficiency of these compounds was increased in order of three (Chol-PRO) < four (Chol-BTA) < two (Chol-ETA) methylene unit in their spacer, and was decreased by an addition of isomethyl group to Chol-PRO spacer. In case of the presence of multiple bonds in the spacer, it required the more cationic lipids in liposome formulation than single bond in the spacer to present similar transfection efficiency. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.