胆固醇乙醚 | 986-19-6

• 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
• 中文名称: 胆固醇乙醚
• 英文名称: 3-ethylcholesterol
• 英文别名: cholester-3β-yl ethyl ether；(3β)-3-ethoxycholest-5-ene；O-ethyl-cholesterol；O-Aethyl-cholesterin；3β-Aethoxy-cholesten-(5)；Aethyl-cholesteryl-aether；Cholesterin ethyl ether；(3S,8S,9S,10R,13R,14S,17R)-3-ethoxy-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]phenanthrene
• CAS: 986-19-6
• 化学式: C₂₉H₅₀O
• 分子量: 414.715
• InChiKey: HVJCKZFYZWPQOO-AXYOXNHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  胆固醇乙醚 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 5α-hydroxy-6β-acryloxy-3-ethylcholesterol
  参考文献：
  名称：

  Synthesis and characterisation of new types of side chain cholesteryl polymers

  摘要：

  A series of cholesterol derivatives have been synthesised via the alkylation reaction of the 3-hydroxyl group with the aliphatic bromide compounds with different chain lengths. namely 3 beta-alkyloxy-cholesterol. The double bond between the C5 and C6 positions in these cholesterol derivatives was oxidised into epoxy, followed by an epoxy-ring-opening reaction with the treatment with acrylic acid, resulting in a series of 3 beta-alkyloxy-5 alpha-hydroxy-6 beta-acryloyloxycholesterol, C(n)OCh (n = 1, 2, 4, 6, 8, 10, 12), The acrylate group is connected to the C6 position, which is confirmed by the single crystal structure analysis. The corresponding polymers, PC(n)OCh, were prepared via free radical polymerisation. The structure of monomers and the resulting polymers were characterised with nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR) and gel permeation chromatography (GPC). The thermal properties of PC(n)OCh were studied using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). To determine the secondary structure of polymers, circular dichroism (CD) spectra were performed. It was found that not all monomers produce high-molecular-weight polymers because of steric hindrance. However, all polymers have a helical structure, which can be enhanced by increasing the alkoxy chain length. In addition, increasing the alkoxy chain length decreases the glass transition temperature and increases the decomposition temperature of the polymers. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.011
• 作为产物：
  描述：

  1-氯-3-甲基丁烷 在 1% Pd on activated carbon 、 ammonium acetate 、 氢气 、 三苯基膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.5h， 生成 胆固醇乙醚
  参考文献：
  名称：

  一种以豆甾醇降解物为原料合成胆固醇的方 法

  摘要：

  本发明提出一种以豆甾醇降解物为原料合成胆固醇的方法，包括步骤：1)3‑羰基‑4‑烯孕甾‑22‑醛与原甲酸三乙酯进行醚化反应，得3‑乙氧基‑3,5‑二烯孕甾‑22‑醛；2)制备3‑甲基丁基三苯基氯化膦溶液；3)3‑甲基丁基三苯基氯化膦溶液中加叔丁醇钾，与3‑乙氧基‑3,5‑二烯孕甾‑22‑醛进行wittig反应，得3‑乙氧基‑3,5,22‑三烯胆甾烷；4)催化3‑乙氧基‑3,5,22‑三烯胆甾烷进行选择性氢化反应，得3‑乙氧基‑5‑烯胆甾烷；5)与醋酐反应得3‑乙酰‑5‑烯胆甾烷；6)3‑乙酰‑5‑烯胆甾烷水解反应得胆固醇。本合成方法工艺简单，利用廉价易得的豆甾醇降解物为原料，胆固醇摩尔收率达85％以上；生产成本低，工艺环保，既经济环保又便于工业化实施。

  公开号：

  CN105218610B

文献信息

• Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 8. Synthesis and properties of O-alkyl selenoesters
  作者：Derek H. R. Barton、Per-Egil Hansen、Kelvin Picker

  DOI：10.1039/p19770001723

  日期：——

  from the appropriate di-N-substituted imidoyl chloride with use of sodium hydrogen selenide to introduce selenium. The reduction of selenoesters to ethers has been demonstrated, as well as the ready reaction of these compounds with the methylene Wittig reagent.

  由适当的二-N-取代的亚氨基酰氯，利用硒化氢钠引入硒，已经合成了多种脂族和芳族的O-烷基硒酸酯。已经证明了硒酸酯还原成醚，以及这些化合物与亚甲基维蒂希试剂的现成反应。
• SNAAP Sulfonimidate Alkylating Agent for Acids, Alcohols, and Phenols
  作者：Tom Maricich、Matthew Allan、Brett Kislin、Andrea Chen、Fan-Chun Meng、Christine Bradford、Nai-Chia Kuan、Jeremy Wood、Omonigho Aisagbonhi、Alethea Poste、Dustin Wride、Sylvia Kim、Therese Santos、Michael Fimbres、Dianne Choi、Haydi Elia、Joseph Kaladjian、Ali Abou-Zahr、Arturo Mejia

  DOI：10.1055/s-0033-1339921

  日期：——

  iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations:

  摘要 稳定，晶状ñ -叔丁基-4- nitrobenzenesulfonimidate已经通过直接O形乙基高收率制备ñ -叔丁基-4-硝基苯磺酰胺与碘乙烷和二氯甲烷银（I）氧化物。该亚磺酸磺酸盐将各种酸直接乙基化为酯。酸越强，烷基化速度越快，收率越高。在四氟硼酸催化剂存在下，在室温下容易将醇和酚乙基化为醚，而不会发生分子重排或外消旋化。我们定义这些反应如烷基化SNAAP：小号ubstitution，Ñ的ucleophilic一个的CID，一个lcohols和p henols]。所述硬sulfonimidate烷化剂是化学选择性的，宁愿氧气>氮气>硫。烷基化的磺酰胺副产物易于再循环至磺酰亚胺酯。 稳定，晶状ñ -叔丁基-4- nitrobenzenesulfonimidate已经通过直接O形乙基高收率制备ñ -叔丁基-4-硝基苯磺酰胺与碘乙烷和二氯甲烷银（I）氧化物。该亚磺酸磺酸盐将各种酸直
• 3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates
  作者：Aneta M Tomkiel、Adam Biedrzycki、Jolanta Płoszyńska、Dorota Naróg、Andrzej Sobkowiak、Jacek W Morzycki

  DOI：10.3762/bjoc.11.16

  日期：——

  3α,5α-Cyclocholestan-6β-yl alkyl and aryl ethers were proved to be efficient cholesteryl donors in the electrochemical synthesis of glycoconjugates. 3α,5α-Cyclocholestan-6β-ol (i-cholesterol) and its tert-butyldimethylsilyl ether can also be used for this purpose. The i-cholesterol derivatives show similar reactivities to those of previously studied 3α,5α-cyclocholestan-6β-thioethers.

  3α,5α-环胆甾烷-6β-基烷基和芳基醚被证明是在糖脂共轭物的电化学合成中高效的胆固醇供体。3α,5α-环胆甾烷-6β-醇（i-胆固醇）及其tert-丁基二甲基硅醚也可用于此目的。i-胆固醇衍生物显示出与先前研究的3α,5α-环胆甾烷-6β-硫醚类似的反应性。
• Conversion of esters and lactones to ethers via thionoesters and thionolactones using reductive radical desulfurization
  作者：Doo Ok Jang、Seong Ho Song、Dae Hyan Cho

  DOI：10.1016/s0040-4020(98)01156-9

  日期：1999.3

  Various thionoesters and thionolactones are readily reduced into the corresponding ethers in high isolated yields by radical desulfurization with organotin hydrides and Et3B under mild reaction conditions.

  通过在温和的反应条件下用有机锡氢化物和Et 3 B进行自由基脱硫，可以轻松地以高分离的收率将各种硫代酸酯和硫代内酯还原为相应的醚。
• Ozonolysis of cholesterol and other Δ5-steroids in the presence of alcohols: a revised mechanism and hydroperoxide structure of the solvent-participated product, confirmed by X-ray analysis
  作者：Zdzisław Paryzek、Urszula Rychlewska

  DOI：10.1039/a702633a

  日期：——

  The structure of the product formed in the course of the reaction of cholesterol acetate and other Δ5-steroids with ozone in alcohol-containing solvents has been revised. The solvent-participated products are hydroperoxides, 5α-hydroperoxy-7α-alkoxy-5α-B-homo-6-oxasteroids 3 and not the previously claimed cyclic hemiperacetals, 5α-hydroxy-7a-alkoxy-B-dihomo-6,7-dioxacholestane derivatives 1. The final

  形成在胆甾醇乙酸酯的反应和其它Δ的过程中对产品的结构5在含醇的溶剂-steroids用臭氧已经修订。参与溶剂的产物是氢过氧化物，5α-氢过氧-7α-烷氧基-5α-B-homo-6-氧杂类固醇3而不是先前要求保护的环状半缩醛，5α-羟基-7a-烷氧基-B-dihomo-6,7-二氧杂胆甾烷衍生物1.从选定的氢过氧化物3a，3c和3j的X射线晶体结构分析中获得了最后的证据。提出涉及氢过氧基和烷氧基的氢键负责这些氢过氧化物的稳定性，并且在醇对Criegee中间体12的亲核进攻中也起指导作用。