2β,3β-epoxy-5α-androstan-17-one | 7676-05-3

• 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: 2β,3β-epoxy-5α-androstan-17-one
• 英文别名: (1S,2S,4S,6R,8S,11R,12S,16S)-2,16-dimethyl-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-one
• CAS: 7676-05-3
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: WPLCXMVUVAWRQC-LTIOPTMSSA-N

物化性质

• 熔点：
  121-123 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  397.2±35.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2β,3β-epoxy-5α-androstan-17-one 在 吡啶 、 lithium aluminium tetrahydride 、 高氯酸 作用下， 以 乙醚 、 苯 为溶剂， 生成 17β-Hydroxy-3α-cyclopentyloxy-5α-androstan
  参考文献：
  名称：

  Gardi,R. et al., Gazzetta Chimica Italiana, 1962, vol. 92, p. 632 - 646

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 2β,3β-epoxy-5α-androstan-17-one
  参考文献：
  名称：

  Fajkos; Sorm, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 3115,3128

  摘要：

  DOI：

文献信息

• Facile Synthesis of Steroidal Vicinal Hydroxysulfides via the Reaction of Steroidal Epoxides with Thiols in the Presence of an Ionic Liquid
  作者：Rita Skoda-Földes、Anita Horváth、Dávid Frigyes、Sándor Mahó、Zoltán Berente、László Kollár

  DOI：10.1055/s-0029-1217031

  日期：2009.12

  can be carried out effectively in the Brønsted acidic ionic liquid [Hmim]+[BF4]- as a recyclable solvent and catalyst. The use of other ionic liquids/molten salts resulted in a decrease in the conversion and/or in reduced selectivity. In [bmim]+Br-, a conversion of 2,3-epoxy-17-ones into 2,17- and 3,17-diones was also observed. catalysis - epoxides - ionic liquids - ring-opening - steroids - thiols

  可以在布朗斯台德酸性离子液体[Hmim] + [BF 4 ] -作为可循环利用的溶剂和催化剂中，有效地进行甾族2,3-环氧化物与硫醇的开环。使用其他离子液体/熔融盐会导致转化率降低和/或选择性降低。在[BMIM] +溴-，2,3-环氧-17-酮转化成2,17-和3,17-二酮，也观察到。 催化-环氧化物-离子液体-开环-类固醇-硫醇
• Selective ring-opening carbonylation of epoxy-steroids☆
  作者：Attila Balázs、Csilla Benedek、Gábor Szalontai、Szilárd Tőrös

  DOI：10.1016/j.steroids.2004.02.003

  日期：2004.4

  Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co-2(CO)(8)/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each case, accompanied by inversion of the original configuration. No carbonylation took place for sterically hindered steranic epoxides. (C) 2004 Elsevier Inc. All rights reserved.
• Facile ring opening of 2,3-epoxy-steroids with aromatic amines in ionic liquids
  作者：Anita Horváth、Rita Skoda-Földes、Sándor Mahó、Zoltán Berente、László Kollár

  DOI：10.1016/j.steroids.2006.04.006

  日期：2006.8

  Efficient ring opening of steroidal 2,3-epoxides with stoichiometric amount of aromatic amines has been carried out using an ionic liquid ([bmim](+)[BF4](-)) both as solvent and catalyst. The reactions were completely regio- and stereoselective in each case. The aminoalcohol products have chair conformations in ring A. The ionic liquid-mediated ring opening can efficiently be carried out with aliphatic amines like morpholine as well. (c) 2006 Elsevier Inc. All rights reserved.