5α-cholestane-3β,5,6β-triol triacetate | 2572-55-6

• 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: 5α-cholestane-3β,5,6β-triol triacetate
• 英文别名: 5α-cholestane-3β,5α,6β-triyl triacetate；5α-cholestane-3β,5α,6β-triol triacetate；cholestane-3β,5α,6β-triyl triacetate；5α-cholestan-3β,5,6β-triol triacetate；(10R)-3c.5t.6c-Triacetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；5α-Cholestan-3β,5α,6β-triol-triacetat；5α-cholestanetriyl-(3β.5.6β)-triacetate；5α-Cholestantriyl-(3β.5.6β)-triacetat；3β.5.6β-Triacetoxy-5α-cholestan；[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5,6-diacetyloxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 2572-55-6
• 化学式: C₃₃H₅₄O₆
• 分子量: 546.788
• InChiKey: NRIMSGFXGPTUAF-ALIDYZMFSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  566.3±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5α-cholestane-3β,5,6β-triol triacetate 在 氢氧化钾 、 硫酸 作用下， 生成 5α-methoxycholestane-3β,6β-diol
  参考文献：
  名称：

  Hattori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 416; engl. Ref. S. 131

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇醋酸酯 在 双氧水 、 溶剂黄146 作用下， 生成 5α-cholestane-3β,5,6β-triol triacetate
  参考文献：
  名称：

  Hattori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 416; engl. Ref. S. 131

  摘要：

  DOI：

文献信息

• Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids
  作者：Peter Yates、Shirley Stiver

  DOI：10.1139/v87-369

  日期：1987.9.1

  Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one (11 and 13) and their 3β-acetoxy (10 and 21) and 3β-benzyloxy derivatives (12 and 19) are described, as are syntheses of the 7α-deutero derivatives of 10 and 21. Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of these compounds are also discussed. Treatment of 12 with potassium tert-butoxide has been shown to give 5-hydroxy-5β-cholest-3-en-6-one (14) and its Δ² isomer 15. Reaction of 6-nitrocholesteryl acetate (50) with lithium dimethylcuprate gives 3α,5-cyclo-5α-cholestan-6-one (E)-oxime (51) as the major product.

  合成了5-羟基-5α-和5β-胆甾烷-6-酮（11和13）及其3β-乙酰氧（10和21）和3β-苄氧衍生物（12和19），并描述了它们的合成，以及10和21的7α-氘代衍生物的合成。还讨论了这些化合物的5-甲氧基和5-甲基类似物的合成研究。已经证明，用叔丁氧化钾处理12可产生5-羟基-5β-胆甾-3-烯-6-酮（14）及其Δ2异构体15。6-硝基胆固醇醋酸酯（50）与二甲基亚铜酸锂反应，主要产物是3α，5-环-5α-胆甾烷-6-酮（E）-肟（51）。
• Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols
  作者：Anthony G. M. Barrett、Christopher R. A. Godfrey、David M. Hollinshead、Panayiotis A. Prokopiou、Derek H. R. Barton、Robin B. Boar、Laurette Joukhadar、James F. McGhie、Satish C. Misra

  DOI：10.1039/p19810001501

  日期：——

  Diverse carboxylic esters have been reduced with dissolving Group 1A metals. Using lithium in ethylamine, sterically hindered esters (RCO2R′) were deoxygenated giving the alkane (R′H) whereas non-hindered esters regenerated the parent alcohol (R′OH). This permitted the selective deoxygenation of diesters. Conversely, potassium–sodium eutectic solubilised with 18-crown-6 in t-butylamine and tetrahydrofuran

  溶解1A族金属可还原各种羧酸酯。使用乙胺中的锂，将位阻酯（RCO 2 R'）脱氧，得到烷烃（R'H），而无阻酯则再生出母体醇（R'OH）。这允许二酯的选择性脱氧。相反，用18-crown-6溶解于叔丁胺和四氢呋喃（THF）中的钾钠共晶可有效地对受阻酯和非受阻酯进行脱氧。在室温下不存在亲核试剂的情况下，羧酸酯基团阴离子的主要反应是脱氧。
• A Fast and Convenient Procedure for the Acetylation of Alcohols
  作者：Roxana Martinez‐Pascual、Omar Viñas‐Bravo、Socorro Meza‐Reyes、Martín. A. Iglesias‐Arteaga、Jesús Sandoval‐Ramírez

  DOI：10.1081/scc-200043272

  日期：2004.1

  Abstract Treatment of different steroidal and aliphatic alcohols with BF3 · OEt2 and acetic anhydride for 5 seconds produced complete acetylation in high to quantitative yields.

  摘要 用 BF3·OEt2 和乙酸酐处理不同的甾族醇和脂肪醇 5 秒，以高到定量的收率产生完全乙酰化。
• Metal–amine reduction of sterically hindered esters to alkanes, a new method for the deoxygenation of hindered alcohols
  作者：Robin B. Boar、Laurette Joukhadar、James F. McGhie、Satish C. Misra、Anthony G. M. Barrett、Derek H. R. Barton、Panayiotis A. Prokopiou

  DOI：10.1039/c39780000068

  日期：——

  Acetates of sterically hindered secondary alcohols and of tertiary alcohols are reduced by lithium in ethylamine to afford predominantly the corresponding alkanes, rather than the parent alcohols.

  位阻仲醇和叔醇的乙酸盐被乙胺中的锂还原，主要得到相应的烷烃，而不是母体醇。
• Barton, Derek H. R.; Goektuerk, A. Kayhan; Morzycki, Jacek W., Journal of the Chemical Society. Perkin transactions I, 1985, p. 583 - 586
  作者：Barton, Derek H. R.、Goektuerk, A. Kayhan、Morzycki, Jacek W.、Motherwell, William B.

  DOI：——

  日期：——