2α-acetoxy-5α-cholestan-3-one | 14161-45-6

• 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: 2α-acetoxy-5α-cholestan-3-one
• 英文别名: 3-oxocholestan-2α-yl acetate；2α-acetoxycholestan-3-one；3-oxo-5α-cholestan-2α-yl acetate；2α-acetoxy-(5α)-cholestan-3-one；2α-Acetoxy-5α-cholestan-3-on；[(2R,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-2-yl] acetate
• CAS: 14161-45-6
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: JRLVDQSYDDODPL-FNUGKIMXSA-N

物化性质

• 沸点：
  513.9±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2α-acetoxy-5α-cholestan-3-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以91%的产率得到2α-acetoxy-5α-cholestan-3β-ol
  参考文献：
  名称：

  类固醇的邻二醇的区域选择性酶酰化

  摘要：

  完整的甾族化合物的2，3-和3，4-邻位二醇的单酰化衍生物是通过区域选择性脂肪酶催化的酯交换反应制备的。取决于羟基的构型，酶对邻二醇具有不同的选择性。

  DOI：

  10.1016/j.tet.2005.01.104
• 作为产物：
  描述：

  anti-oxime of 5α-cholestan-3-one 在 吡啶 、 单过氧邻苯二甲酸 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 2α-acetoxy-5α-cholestan-3-one
  参考文献：
  名称：

  Boar,R.B. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1237 - 1241

  摘要：

  DOI：

文献信息

• Novel and efficient synthesis and antifungal evaluation of 2,3-functionalized cholestane and androstane derivatives
  作者：Branko S. Jursic、Sunil Kumar Upadhyay、Clinton C. Creech、Donna M. Neumann

  DOI：10.1016/j.bmcl.2010.10.044

  日期：2010.12

  to the development of efficient syntheses of building blocks for novel fatty-acid esters of steroids. In this Letter, we outline a novel and efficient approach to the synthesis of 2,3-functionalized cholestane and androstane derivatives and present their promising preliminary antifungal activities against a number of fungal species.

  胆固醇和其他传统类固醇分子的合成修饰已成为探索和开发新型抗真菌剂的有前途的领域，尤其是在类固醇脂肪酸酯的开发方面。另外，2，3-官能化的类固醇也是具有潜在令人感兴趣的生物学性质的化合物，并且2，3-类固醇的适当官能化可以导致开发有效合成的类固醇的脂肪酸酯的结构单元。在这封信中，我们概述了合成2，3-官能化的胆甾烷和雄烷酮衍生物的新颖而有效的方法，并提出了它们对许多真菌物种的有希望的初步抗真菌活性。
• Autoxidation vs Hydrolysis in 16α-Acyloxy Steroids
  作者：Barbora Slavíková、Alexander Kasal、Miloš Buděšínský

  DOI：10.1135/cccc19991125

  日期：——

  Some enolizable α-hydroxy ketones are extremely susceptible to oxidation with traces of air in a reaction vessel. Autoxidation can be used in synthesis of oxo acids or diacids and their derivatives. Yet alkaline hydrolysis of the substrate is possible though under strictly air-free conditions.

  一些可发酵的α-羟基酮在反应容器中受到微量空气氧化的影响非常容易。自氧化可以用于合成羧酸或二酸及其衍生物。然而，底物的碱性水解在严格无空气条件下也是可能的。
• Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1
  作者：Clayton H. Heathcock、Stephen C. Smith

  DOI：10.1021/jo00101a052

  日期：1994.11

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.
• .alpha.-Halo ketones. 10. Regiospecific homologation of unsymmetrical ketones
  作者：Vinod Dave、E. W. Warnhoff

  DOI：10.1021/jo00163a034

  日期：1983.7
• Dave, Vinod; Stothers, J. B.; Warnhoff, E. W., Canadian Journal of Chemistry, 1980, vol. 58, p. 2666 - 2678
  作者：Dave, Vinod、Stothers, J. B.、Warnhoff, E. W.

  DOI：——

  日期：——