3α,4α-epoxyandrost-5-ene-7,17-dione | 204270-50-8

• 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: 3α,4α-epoxyandrost-5-ene-7,17-dione
• 英文别名: (1S,2R,5R,7S,11R,12S,16S)-2,16-dimethyl-6-oxapentacyclo[9.7.0.02,8.05,7.012,16]octadec-8-ene-10,15-dione
• CAS: 204270-50-8
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: QUJFMSJPJMRXQJ-BFDDTPHTSA-N

物化性质

• 沸点：
  461.0±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α,4α-epoxyandrost-5-ene-7,17-dione 在 吡啶 、 sodium acetate 、 溶剂黄146 作用下， 反应 38.0h， 生成 (8R,9S,10R,13S,14S)-10,13-二甲基-1,2,3,8,9,11,12,14,15,16-十氢环戊烯并[a]菲-4,7,17-三酮
  参考文献：
  名称：

  Hanson, James R.; Kiran, Ismail; Masarwah, Natheer F., Journal of Chemical Research, Miniprint, 1998, # 9, p. 2420 - 2434

  摘要：

  DOI：
• 作为产物：
  描述：

  雄甾-3,5二烯-7,17-二酮 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以850 mg的产率得到3α,4α-epoxyandrost-5-ene-7,17-dione
  参考文献：
  名称：

  Bourban, Caroline Y. M.; Hanson, James R.; Kiran, Ismail, Journal of Chemical Research, Miniprint, 1997, # 12, p. 2847 - 2859

  摘要：

  DOI：

文献信息

• METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS
  申请人：Ge Yu

  公开号：US20120214987A1

  公开（公告）日：2012-08-23

  The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5a-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.

  该发明涉及制备3α-O-连接类固醇的过程，包括3α-O-连接-雄烯类固醇和3α-O-连接-5α-雄烷类固醇。在一个过程中，3α,4α-环氧基雄-5-烯-17-酮主要在环氧基团处还原，其中3α,4α-环氧官能团的还原优先发生在C4位置，并保留C3位置的构型，以提供3α-O-连接-雄烯类固醇。在另一个过程中，通过Mitsunobu反应提供条件，使3β-羟基雄-5-烯类固醇的构型发生倒置，以提供含有减少量3α,5α-环雄烷副产物杂质的3α-O-连接-雄烯类固醇。
• Hanson, James R.; Hitchcock, Peter B.; Nagaratnam, Sivajini, Journal of Chemical Research, Miniprint, 1999, # 1, p. 319 - 346
  作者：Hanson, James R.、Hitchcock, Peter B.、Nagaratnam, Sivajini

  DOI：——

  日期：——
• [EN] METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS<br/>[FR] PROCÉDÉS ET COMPOSÉS UTILISÉS POUR PRÉPARER DES STÉROÏDES 3 ALPHA-OXYGÈNE SUBSTITUÉS
  申请人：HARBOR BIOSCIENCES INC

  公开号：WO2012083090A2

  公开（公告）日：2012-06-21

  The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5α-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.
• Hanson, James R.; Kiran, Ismail; Masarwah, Natheer F., Journal of Chemical Research, Miniprint, 1998, # 9, p. 2420 - 2434
  作者：Hanson, James R.、Kiran, Ismail、Masarwah, Natheer F.、Uyanik, Cavit

  DOI：——

  日期：——
• Bourban, Caroline Y. M.; Hanson, James R.; Kiran, Ismail, Journal of Chemical Research, Miniprint, 1997, # 12, p. 2847 - 2859
  作者：Bourban, Caroline Y. M.、Hanson, James R.、Kiran, Ismail

  DOI：——

  日期：——