O-三甲基硅烷基胆固醇 | 1856-05-9

• 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: O-三甲基硅烷基胆固醇
• 英文名称: cholesterol trimethylsilyl ether
• 英文别名: [(3β-cholest-5-en-3-yl)oxy]trimethylsilane；trimethyl[(3β)-cholest-4-en-3-yloxy]silane；(3β)-3-[(trimethylsilyl)oxy]cholest-5-ene；trimethyl[3β-cholest-4-en-3-yloxy]silane；cholest-5-en-3β-ol trimethylsilyl ether；Cholesterol trimethylsilyl ester；O-Trimethylsilylcholesterol；[(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-trimethylsilane
• CAS: 1856-05-9
• 化学式: C₃₀H₅₄OSi
• 分子量: 458.844
• InChiKey: CBVJJGRSRFXUPK-OCBUSCMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  32
• 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：

  O-三甲基硅烷基胆固醇 在 tripropylammonium fluorochromate (VI) 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到4-胆甾烯-3-酮
  参考文献：
  名称：

  Desilylative Oxidation of Alkyl Trimethylsilyl Ethers with Pyridinium Fluorochromate

  摘要：

  AbstractDirect conversion of alkyl trimethylsilyl ethers to carbonyl compounds is accomplished using PFC in dichloromethane at room temperature. For a similar oxidation of t‐butyldimethylsilyl ethers the PCC‐n‐Bu4NF combination may be employed.

  DOI：

  10.1002/jccs.199900089
• 作为产物：
  描述：

  胆固醇 生成 O-三甲基硅烷基胆固醇
  参考文献：
  名称：

  TAKATSUTO, SUGURU;OMOTE, KUMIKO;KITSUWA, TAKAHARU, AGR. AND BIOL. CHEM., 53,(1989) N, C. 2277-2278

  摘要：

  DOI：

文献信息

• 1,3-Dichloro-5,5-Dimethylhydantoin (DCH) and Trichloromelamine (TCM) as Efficient Catalysts for the Chemoselective Trimethylsilylation of Hydroxyl Group with 1,1,1,3,3,3-Hexamethyldisilazane (HMDS) Under Mild Conditions
  作者：Arash Ghorbani-Choghamarani、Kamal Amani、Mohammad Ali Zolfigol、Maryam Hajjami、Roia Ayazi-Nasrabadi

  DOI：10.1002/jccs.200900037

  日期：2009.4

  A highly convenient method for the trimethylsilylation of alcohols and phenols via treatment by hexamethyldisilazane in the presence of 1,3–dichloro‐5,5–dimethylhydantoin (DCH) and/or trichloromelamine (TCM) as a catalyst has been developed. A wide variety of hydroxyl groups were selectively protected in CH2Cl2/CH3CN under mild conditions.

  已经开发了一种非常方便的方法，用于在1，3-二氯-5，5-二甲基乙内酰脲（DCH）和/或三氯三聚氰胺（TCM）作为催化剂存在下，通过六甲基二硅氮烷进行处理，对醇和酚进行三甲基甲硅烷基化。在温和的条件下，在CH 2 Cl 2 / CH 3 CN中选择性保护了多种羟基。
• A Mild, Simple, Efficient, and Selective Protection of Hydroxyl Groups Using Silica-Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst
  作者：Hamid Reza Shaterian、Razieh Doostmohammadi、Majid Ghashang、Mashaallah Rahmani

  DOI：10.1080/10426500802066054

  日期：2008.11.7

  A mild, simple, novel, and highly efficient method for the rapid protection of various primary, secondary, tertiary aliphatic alcohols, aromatic alcohols, and oximes using hexamethyldisilazane (HMDS) in the presence of silica-supported sodium hydrogen sulfate (NaHSO 4 -SiO 2 ), as an active, inexpensive, nontoxic, heterogeneous, and readily available catalyst under ambient conditions is described.

  一种温和、简单、新颖且高效的方法，可在二氧化硅负载的硫酸氢钠 (NaHSO 4 -SiO) 存在下使用六甲基二硅氮烷 (HMDS) 快速保护各种伯、仲、叔脂肪醇、芳香醇和肟2 )，描述了在环境条件下作为活性、廉价、无毒、非均相和容易获得的催化剂。在室温下温和且几乎中性的反应条件下，以高产率制备三甲基甲硅烷基醚，反应时间短。
• A Highly Efficient Method for the Silylation of Alcohols, Phenols, and Naphthols Using HMDS in the Presence of Zinc Oxide (ZnO) as Economical Heterogeneous Catalyst
  作者：Hamid Reza Shaterian、Majid Ghashang

  DOI：10.1080/10426500701569406

  日期：2007.12.24

  Variety alcohols, phenols, and naphthols were effectively converted into their corresponding trimethylsilyl ether with hexamethyldisilazane in the presence of zinc oxide under very mild and ambient conditions with short reaction time in good to excellent yields.

  在氧化锌的存在下，在非常温和的环境条件下，各种醇类、酚类和萘酚类与六甲基二硅氮烷一起有效转化为相应的三甲基甲硅烷基醚，反应时间短，收率良好。
• [EN] DETECTION OF CHOLESTEROL OZONATION PRODUCTS<br/>[FR] DETECTION DE PRODUITS D'OZONATION DU CHOLESTEROL
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2005023831A1

  公开（公告）日：2005-03-17

  The invention relates to detection of cholesterol ozonation products that are generated by atherosclerotic plaque material, and to methods of detecting vascular conditions that relate to the accumulation and oxidation of cholesterol.

  这项发明涉及检测由动脉粥样硬化斑块材料产生的胆固醇臭氧化产物，以及检测与胆固醇积聚和氧化有关的血管状况的方法。
• Trimethylsilyl chloride-accelerated reduction and pinacol coupling of carbonyl compounds by means of samarium diiodide
  作者：Toshio Honda、Miho Katoh

  DOI：10.1039/a607774i

  日期：——

  The combination of samarium diiodide (SmI 2 ) and trimethylsilyl chloride (Me 3 SiCl) in THF–HMPA is found to accelerate the reduction of sterically hindered and enolisable ketones, and also to accelerate pinacolisation of the carbonyl compounds depending on the reaction conditions.

  在THF-HMPA中，联碘钐（SmI2）和三甲基氯硅烷（Me3SiCl）的组合被发现能加速空间位阻性大且可烯醇化的酮的还原作用，并且在特定反应条件下也能加速羰基化合物的频哪醇重排反应。