3-(4-hydroxybutyl)cholesterol | 141881-91-6

• 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-(4-hydroxybutyl)cholesterol
• 英文别名: 4-[[(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]butan-1-ol
• CAS: 141881-91-6
• 化学式: C₃₁H₅₄O₂
• 分子量: 458.769
• InChiKey: KXTQADSDRHLJMP-BWVDWJPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 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-(4-hydroxybutyl)cholesterol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 4-(((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)oxy)-N,N,N-trimethylbutan-1-aminium bromide
  参考文献：
  名称：

  The synthesis of cholesterol-based cationic lipids with trimethylamine head and the effect of spacer structures on transfection efficiency

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.04.071
• 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 22.0h， 生成 3-(4-hydroxybutyl)cholesterol
  参考文献：
  名称：

  通过调整主链结构和灵活的间隔基长度来自组织胆固醇侧链液晶聚合物

  摘要：

  三种侧链液晶聚合物（SCLCP），其中胆甾醇型液晶元（Chol）与聚丙烯酸酯（PCholAC- m），聚甲基丙烯酸酯（PCholMC- m）和聚（2-乙烯基苯-1,4-二酸酯）连接通过自由基聚合成功地合成了通过不同长度（m = 0、2、4、6、8和10）的亚甲基间隔基形成的（PCholVA- m）主链。使用DSC，POM和SAXS详细研究了聚合物的相行为和结构。结果表明，通过改变主链结构和间隔区长度，Chol-SCLCPs表现出有趣的自组织。所述聚合物最初形成近晶A相，除了没有液晶相的PCholAC-0以外。接下来，聚合物PCholAC-m（m＝ 2、4、6）形成两层近晶A相，其中烷基尾部重叠（SmA 2）。在PCholAC- m（m = 8，10）中观察到两相共存结构，包括双层近晶A相（其中烷基尾部插入到液晶元中）（SmA d）和单层近晶A相，其中液晶元重叠（SmA 1）。对于PCholMC-

  DOI：

  10.1039/c8nj06168h

文献信息

• STEROLS MODIFIED BY POLYETHYLENE GLYCOL, THE PREPARATION AND THE USE THEREOF
  申请人：Zhang Wenfang

  公开号：US20100036140A1

  公开（公告）日：2010-02-11

  The invention provides sterols modified by polyethylene glycol represented by the following formula, the preparation and the use thereof, wherein each symbol is defined as in the description.

  这项发明提供了由以下公式表示的聚乙二醇修饰的甾醇，以及其制备和使用，其中每个符号的定义如描述中所述。
• Phospholipidation of TLR7/8-active imidazoquinolines using a tandem phosphoramidite method
  作者：Hélène G. Bazin、Laura S. Bess、Mark T. Livesay、Sandra C. Mwakwari、David A. Johnson

  DOI：10.1016/j.tetlet.2016.03.091

  日期：2016.5

  1-imidazoquinolinylalkanols. The resulting phosphite can be purified or directly oxidized with t-butyl hydroperoxide. The cyanoethyl protecting group is then removed with triethylamine and the phospholipidated imidazoquinoline products isolated in good yield and purity by simple filtration.

  开发了一种高产且可扩展的亚磷酰胺工艺，用于 TLR7/8 活性咪唑并喹啉的磷脂化。该方法涉及1,2-二酰基-或二烷基-sn-甘油或3-氯甾醇与2-氰基乙基N , N , N ', N'-四异丙基亚磷二酰胺在1H-四唑存在下反应，然后用所得的N , N'-二异丙基亚磷酰胺脂质与 1-咪唑并喹啉基链烷醇原位反应。所得亚磷酸酯可以纯化或直接用叔丁基过氧化氢氧化。然后用三乙胺除去氰乙基保护基团，并通过简单的过滤以良好的产率和纯度分离磷脂化的咪唑喹啉产物。
• WO2008/103276
  申请人：——

  公开号：——

  公开（公告）日：——
• Anion-Selective Cholesterol Decorated Macrocyclic Transmembrane Ion Carriers
  作者：Harekrushna Behera、Nandita Madhavan

  DOI：10.1021/jacs.7b07479

  日期：2017.9.20

  Anion transporters play a vital role in cellular processes and their dysregulation leads to a range of diseases such as cystic fibrosis, Bartters syndrome and epilepsy. Synthetic chloride transporters are known to induce apoptosis in cancer cell lines. Herein, we report triamide macrocycles that are easily synthesized and externally functionalized by pendant membrane-permeable groups. Among a variety of chains appended onto the macrocycle scaffold, cholesterol is found to be the best with an EC50 value of 0.44 mu M. The macrocycle is highly anion-selective and transports ions via an OH-/X- antiport mechanism. The macrocycle is an interesting scaffold for ion-transport as it is able to discriminate between various anions and shows a preference for SCN- and Cl-. Such anion-selective transporters are highly attractive model systems to study ion-transport mechanisms and could potentially be of high therapeutic value.
• Regioselective C(sp3) Carboboration of 1,3-Diynes: A Direct Route to Fully Substituted Enyne Boronates
  作者：Suman Ghosh、Shailendra Kumar、Rajesh Chakrabortty、Venkataraman Ganesh

  DOI：10.1021/acs.orglett.4c02109

  日期：2024.8.9