cholest-5-en-3β-yl diphenyl phosphate | 24352-63-4

• 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: cholest-5-en-3β-yl diphenyl phosphate
• 英文别名: cholesteryl diphenylphosphate；Cholesteryl-diphenylphosphat；17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1Hcyclopenta[a]phenanthren-3-yl diphenyl phosphate；phosphoric acid cholesteryl ester-diphenyl ester；Phosphorsaeure-cholesterylester-diphenylester；Cholest-5-en-3-ol (3I(2))-, 3-(diphenyl 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] diphenyl phosphate
• CAS: 24352-63-4
• 化学式: C₃₉H₅₅O₄P
• 分子量: 618.837
• InChiKey: FYUHWYIFVFOEPB-FAFYVPRKSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  642.7±38.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.68
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cholest-5-en-3β-yl diphenyl phosphate 在 四氮唑 、 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cholest-5-en-3β-yl-dimethyl phosphite
  参考文献：
  名称：

  Electrochemical synthesis of glycoconjugates from activated sterol derivatives

  摘要：

  Several derivatives of cholesterol and other 3 beta-hydroxy-Delta(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.01.007
• 作为产物：
  描述：

  cholesterol 、 氯磷酸二苯酯 在 吡啶 作用下， 生成 cholest-5-en-3β-yl diphenyl phosphate
  参考文献：
  名称：

  Δ的磷酸二苯酯的反应；5-固醇

  摘要：

  DOI：

  10.1039/jr9540002301

文献信息

• Substitution- and Elimination-Free Phosphorylation of Functionalized Alcohols Catalyzed by Oxidomolybdenum Tetrachloride
  作者：Cheng-Yuan Liu、Vijay D. Pawar、Jun-Qi Kao、Chien-Tien Chen

  DOI：10.1002/adsc.200900279

  日期：2010.1.4

  the tested alcohols, oxidomolybdenum tetrachloride (MoOCl4) was found to be the most efficient with a negligible background reaction mediated by triethylamine (Et3N). The new catalytic protocol can be applied to the chemoselective phosphorylations of primary, secondary and tertiary alcohols as well as the substitution‐free phosphorylations of allylic, propargylic, and benzylic alcohols. Functionalized

  在检查的14种氧化金属中，被催化的醇催化磷酸化后，四氯化氧化钼（MoOCl 4）在由三乙胺（Et 3 N）介导的可忽略的背景反应中被认为是最有效的。新的催化方案可应用于伯，仲和叔醇的化学选择性磷酸化，以及烯丙基，炔丙基和苄基醇的无取代磷酸化。带有丙酮化物，四氢吡喃基醚，叔丁基的官能化醇叔丁基二甲基甲硅烷基醚或酯基也适用于新的催化方案。最困难的情况涉及1-苯基乙醇和1-（2-萘基）乙醇的无取代磷酸化，分别可以达到95％和90％的收率。反应进展的ESI-MS，IR，1 H和31 P NMR光谱分析表明，烷氧基氧化钼三氯化物-三乙胺加合物如[（RO）Mo（O）Cl 3 -Et 3 N]的中间体催化周转。
• Fluoride-ion-mediated Hydrolysis of Phosphoric Acid Esters, Amides, and Phosphorous Acid Esters Leading to Phosphorofluoridic, Phosphoramide Fluoridic, and Phosphonic Acid Monoester Salts
  作者：Toshiaki Murai、Tohru Takenaka、Shinsuke Inaji、Yusuke Tonomura

  DOI：10.1246/cl.2008.1198

  日期：2008.12.5

  Fluoride-ion-promoted hydrolysis of phosphoric acid esters and amides to give phosphorofluoridic and phosphoramide fluoridic acid monoester salts takes place upon treatment with a THF solution of T...

  在用 THF 的 THF 溶液处理后，氟离子促进磷酸酯和酰胺水解生成氟代磷酸酯和磷酰胺氟酸单酯盐。
• B(C6F5)3 as a Highly Effective Catalyst for the Phosphoryl Transfer Reaction
  作者：Weihua Xue、Lifen Zhang

  DOI：10.1002/cjoc.201200264

  日期：2012.8

  The phosphoryl transfer reactions of diphenyl chlorophosphate with a wide range of alcohols were catalyzed by tris(pentafluorophenyl)boron [B(C6F5)3], giving the corresponding phosphate esters in excellent yields. This methodology has advantages over older ones because it employs the easily handled B(C6F5)3, avoids the side reaction, and has shorter reaction time.

  三（五氟苯基）硼[B（C 6 F 5）3 ]催化氯代磷酸二苯酯与多种醇的磷酰基转移反应，从而以优异的收率得到相应的磷酸酯。该方法比旧方法具有优势，因为它采用了易于处理的B（C 6 F 5）3，避免了副反应，并且反应时间更短。
• 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。
• Montgomery et al., Journal of the Chemical Society, 1956, p. 4603,4606
  作者：Montgomery et al.

  DOI：——

  日期：——