胆固醇磷酸酯 | 4358-16-1

• 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: 胆固醇磷酸酯
• 中文别名: 2,3,6-三氯苯基乙酸钠
• 英文名称: (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 dihydrogen phosphate
• 英文别名: cholesteryl phosphate；cholesteryl dihydrogenphosphate；3β-Phosphonooxy-cholesten-(5)；Phosphorsaeure-monocholesterylester；Cholesteryl-dihydrogenphosphat；Cholesterol phosphate；[(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] dihydrogen phosphate
• CAS: 4358-16-1
• 化学式: C₂₇H₄₇O₄P
• 分子量: 466.642
• InChiKey: AVTXVDFKYBVTKR-DPAQBDIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  胆固醇磷酸酯 在 丙醇 、 硫酸 作用下， 生成 3-(cholesten-(2)-yl-(3))-cholestadiene-(3.5)
  参考文献：
  名称：

  Mueller; Page, Journal of Biological Chemistry, 1933, vol. 101, p. 127,130

  摘要：

  DOI：
• 作为产物：
  描述：

  cholesterol 在 乙醚 、 phosphorus pentoxide 作用下， 生成 胆固醇磷酸酯
  参考文献：
  名称：

  Implications of Interdomain Traffic Characteristics on Traffic Engineering

  摘要：

  AbstractWe study the interdomain traffic as seen by a non‐transit ISP, based on a six days trace covering all the interdomain links of this ISP. Our analysis considers the relationships between the interdomain traffic and the interdomain topology. We first discuss the day‐to‐day stability of the interdomain traffic matrix to evaluate the feasibility of interdomain traffic engineering. Then, we study the variability of the interdomain flows for several aggregation levels (prefix, AS and sink tree) and with respect to the interdomain topology seen by BGP. We show that despite the important variability of interdomain flows, it would be useful for a non‐transit ISP to traffic engineer its access traffic by relying on a sink tree aggregation level.

  DOI：

  10.1002/ett.4460130104

文献信息

• Protection of phosphate with the 9-fluorenylmethyl group. Synthesis of unsaturated-acyl phosphatidylinositol 4,5-bisphosphate
  作者：Yutaka Watanabe、Tomoko Nakamura、Hiroyuki Mitsumoto

  DOI：10.1016/s0040-4039(97)85781-4

  日期：1997.10

  di-(9-fluorenylmethyl) phosphates obtained via phosphitylation were found to be suitable for protection of phosphoric monoesters, which were generated by treatment of the triesters with DBU or triethylamine. This strategy and a hydroxyl protecting group, 2-[2-(levulinoyloxy)ethyl]benzoyl were applied to synthesis of a dioleoyl analog of PI(4,5)P2.

  发现通过磷酸化获得的烷基二-（9-芴基甲基）磷酸酯适用于保护磷酸单酯，磷酸单酯是通过用DBU或三乙胺处理三酯而产生的。该策略和羟基保护基团2- [2-（乙酰丙酰氧基）乙基]苯甲酰基被用于PI（4,5）P 2的油酰基类似物的合成。
• Mild and Chemoselective Phosphorylation of Alcohols Using a Ψ-Reagent
  作者：Michał Ociepa、Kyle W. Knouse、David He、Julien C. Vantourout、Dillon T. Flood、Natalia M. Padial、Jason S. Chen、Brittany B. Sanchez、Emily J. Sturgell、Bin Zheng、Shenjie Qiu、Michael A. Schmidt、Martin D. Eastgate、Phil S. Baran

  DOI：10.1021/acs.orglett.1c02736

  日期：2021.12.17

  An operationally simple, scalable, and chemoselective method for the direct phosphorylation of alcohols using a P(V)-approach based on the Ψ-reagent platform is disclosed. The method features a broad substrate scope of utility in both simple and complex settings and provides access to valuable phosphorylated alcohols that would be otherwise difficult to obtain.

  公开了一种操作简单、可扩展且化学选择性的方法，用于使用基于Ψ-试剂平台的P(V)-方法直接磷酸化醇。该方法的特点是在简单和复杂的环境中具有广泛的底物应用范围，并提供了获得有价值的磷酸化醇的途径，而这些是其他方法难以获得的。
• Some steroid phosphates and related compounds
  作者：R. J. W. Cremlyn、N. A. Olsson

  DOI：10.1039/j39690002305

  日期：——

  cholesteryl phosphorodichloridate has been examined. Reaction of thiophosphoryl chloride and cholesterol gave cholesteryl thionophosphorodichloridate but this could not be hydrolysed to the phosphate. Treatment of cholesterol with phosphorus pentasulphide gave OO-dichol-esteryl hydrogen phosphorodithioate contrary to previous reports. A study has been made of the decomposition of cholesteryl phosphorodichloridate

  描述了通过二氯氯代磷酸氯酯制备磷酸胆固醇基二氢；尽管该反应成功地制备了麦角甾醇酯和羊毛脂酰二氯磷酸酯，但胆固醇和硫代胆固醇的反应却失败了。已经制备了二胆固醇磷酸氯酯，但没有制备二麦角甾醇酯或二癸甾基磷酸氯酯。已经检查了胆固醇二磷酸二氯酯的水解。硫代磷酰氯与胆固醇的反应产生了胆甾醇基硫代磷酸二氯酯，但是它不能被水解为磷酸盐。五硫化二磷处理胆固醇产生OO-二苯甲酸酯基二硫代磷酸氢盐与以前的报道相反。已经进行了在惰性有机溶剂中分解胆固醇的二氯磷酸氯酯的研究。
• Irradiation of diaryl phosphates. A potentially useful new reaction for the preparation of monoalkyl phosphates
  作者：Richard A. Finnegan、James A. Matson

  DOI：10.1039/c3975000928b

  日期：——

  U.v. irradiation of a series of simple dianisyl alkyl phosphates provided the corresponding monoalkyl phosphoric acids in excellent yields.

  一系列简单的二茴香基烷基磷酸的紫外线照射以优异的产率提供了相应的单烷基磷酸。
• Studies of organophosphorochloridates. Part II. Reactions of steroid phosphorodichloridates
  作者：R. J. W. Cremlyn、N. A. Olsson

  DOI：10.1039/j39710002023

  日期：——

  The preparation of the following steroid phosphorodichloridates is described: cholestanyl, epicholestanyl, epicholesteryl, and the derivatives of methyl 3α-hydroxy-5β-chlolanate, and ergosta-8(14)en-3β-ol. The formation of the phosphorodichloridates was followed by t.l.c. Attempted phosphorylation of 3,5-cyclocholestan-6β-ol, and 6β-hydroxycholest-4-en-3-ol gave cholesteryl phosphorodichloridate and

  描述了以下甾族二氯磷酸酯的制备：胆甾烷基，表胆固醇基，表胆固醇基以及3α-羟基-5β-氯戊酸甲酯的衍生物和ergosta-8（14）en-3β-ol。形成二氯二氯磷酸酯后，进行薄层色谱（tlc）。尝试将3,5-环胆甾烷-6β-ol和6β-羟基胆甾醇4-en-3-ol磷酸化，分别得到胆甾醇基二氯磷酸酯和胆甾烷3,6-二酮。已经在各种条件下检查了胆固醇二磷酸二氯酯的水解。类固醇二氯化磷已用甲醇处理。胆磷酸二氯胆固醇酯与多种醇的反应，得到相应的胆甾醇醚。用干燥的吡啶溶剂化二氯化磷，得到相应的N-类固醇吡啶鎓氯化物。