(5,6)α-epoxy-5α-cholestan-3-one 3-cyclic ethylene ketal | 24281-56-9

• 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
• 英文名称: (5,6)α-epoxy-5α-cholestan-3-one 3-cyclic ethylene ketal
• 英文别名: 5,6α-epoxycholestan-3-one, 3-cyclic ethylene ketal；3,3-ethanediyldioxy-5,6α-epoxy-5α-cholestane；3,3-Aethandiyldioxy-5,6α-epoxy-5α-cholestan
• CAS: 24281-56-9
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: KGPVETFFXMOEJP-VTXMWEHDSA-N

物化性质

• 熔点：
  118-120 °C(Solvent: Methanol)
• 沸点：
  521.5±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.99
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5,6)α-epoxy-5α-cholestan-3-one 3-cyclic ethylene ketal 在 甲醇 、 乙醚 作用下， 生成 5α-hydroxy-6β-methylcholestan-3-one
  参考文献：
  名称：

  Cooley et al., Journal of the Chemical Society, 1957, p. 4112,4114

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3-ethane-1,2-diyldioxy-cholest-5-ene 在 单过氧邻苯二甲酸 、 乙醚 、 氯仿 作用下， 生成 (5,6)α-epoxy-5α-cholestan-3-one 3-cyclic ethylene ketal 、 3,3-ethanediyldioxy-5,6β-epoxy-5β-cholestane
  参考文献：
  名称：

  Cooley et al., Journal of the Chemical Society, 1957, p. 4112,4114

  摘要：

  DOI：

文献信息

• A Convenient Synthesis of 5,6β-Epoxides of Some Cholesteryl Esters and Δ⁵-Ketosteroid Derivatives by Catalytic β-Stereoselective Epoxidation
  作者：Jean-Claude Marchon、René Ramasseul

  DOI：10.1055/s-1989-27261

  日期：——

  The epoxidation of a series of cholesteryl esters by air in the presence of a catalytic amount of a ruthenium tetramesitylporphyrin complex is described. The preparative procedure, which requires only 4 to 5 mol % of the catalyst, leads to high conversion (76 to 94 %) and very high β-stereoselectivity (> 99 %). Similar results are obtained in the epoxidation of 3β-acetoxyandrost-5-ene-17-one, 3β-acetoxypregn-5-ene-20-one, and 3,3-ethylenedioxycholest-5-ene.

  报道了在四甲基卟啉钌络合物催化剂存在下，空气对一系列胆固醇酯进行环氧化反应的研究。该制备方法仅需加入4至5摩尔%的催化剂，即可实现高转化率（76至94%）和极高β立体选择性（> 99%）。类似的结果也在3β-乙酰氧基雄甾-5-烯-17-酮、3β-乙酰氧基孕甾-5-烯-20-酮和3,3-亚乙二氧基胆甾-5-烯的环氧化反应中获得。
• Rearrangement of steroidal epoxides and opening of steroidal ketals by alkyllithiums
  作者：Herbert L. Holland、Jahangir

  DOI：10.1016/s0040-4039(00)81714-1

  日期：——

  The ethylene ketal of 5,6α-epoxycholestan-3-one is converted to a ketalised Δ4-6α-ol on treatment with n-BuLi. However, the corresponding β epoxide undergoes opening of the ketal ring in the same reaction. Methyl- and n-butyl-lithium also react with the ethylene ketal of 3-ketocholestanes to give 3-alkyl cholestan-3-ols. The stereoselectivity of this reaction is discussed and a mechanism involving

  5,6α-epoxycholestan -3-酮的亚乙基缩酮被转化为ketalisedΔ 4 -6α醇上治疗用n-BuLi。然而，在相同反应中，相应的β-环氧化物经历了缩酮环的打开。甲基和正丁基锂也与3-酮胆甾醇的乙烯缩酮反应，生成3-烷基胆甾烷-3-醇。讨论了该反应的立体选择性，并提出了涉及1,2氢化物位移的机理。
• Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones
  作者：Dan Yang、Guan‐Sheng Jiao

  DOI：10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#

  日期：2000.10.2

  A general catalytic and environmentally friendly method for beta-epoxidation of Delta(5)-unsaturated steroids has been developed, which uses ketones as the catalysts and Oxone as the terminal oxidant. A whole range of Delta(5)-unsaturated steroids, which bear different functional groups such as hydroxyl, carbonyl, acetyl, or ketal, as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5 beta,5 beta-epoxides with excellent beta-selectivities and high yields.
• Julia,S. et al., Bulletin de la Societe Chimique de France, 1966, p. 2277 - 2283
  作者：Julia,S. et al.

  DOI：——

  日期：——
• Holland, Herbert L.; Jahangir, Canadian Journal of Chemistry, 1983, vol. 61, p. 2165 - 2170
  作者：Holland, Herbert L.、Jahangir

  DOI：——

  日期：——