17α-ethinyl-17-hydroxy-5α-androst-2-eno<2,3-d>isoxazole | 65969-03-1

• 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: 17α-ethinyl-17-hydroxy-5α-androst-2-eno<2,3-d>isoxazole
• 英文别名: 17β-Hydroxy-17α-aethinyl-androstano <2.3-d> isoxazol；(5α,17βH)-pregn-20-yno[2,3-d]isoxazol-17-ol；(1S,2S,10S,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
• CAS: 65969-03-1
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: RVNOYEJRCSZRMY-BSMDRJKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17α-ethinyl-17-hydroxy-5α-androst-2-eno<2,3-d>isoxazole 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 生成 17α-Aethinyl-2α-cyan-androstanol-(17β)-on-(3)
  参考文献：
  名称：

  甾体杂环。七。雄甾烷（2,3-D）异恶唑及相关化合物。

  摘要：

  DOI：

  10.1021/jm00337a001
• 作为产物：
  描述：

  (5α,17α)-2-(hydroxymethylene)-17-hydroxypreg-20-yn-3-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 17α-ethinyl-17-hydroxy-5α-androst-2-eno<2,3-d>isoxazole
  参考文献：
  名称：

  甾体杂环。七。雄甾烷（2,3-D）异恶唑及相关化合物。

  摘要：

  DOI：

  10.1021/jm00337a001

文献信息

• Reaction of Steroidal 17-Acetylenic Alcohols with Diethylamidosulfur Trifluoride and the Structural Assignments of 17-Fluorosteroids
  作者：Virendra Kumar、Charles Rodger、Malcolm R. Bell

  DOI：10.1021/jo00119a042

  日期：1995.7

  Reaction of diethylamidosulfur trifluoride (DAST) with C-17 tertiary alcohols of A-ring-fused steroids, such as Danazol(1), did not furnish the stereochemically coveted C-17 beta-fluoro derivatives. The C-17 alpha-fluoro compounds were isolated as the predominant component of the reaction mixture along with the rearrangement and elimination products. It is postulated that the attack of fluoride ion to the intermediary carbonium ion occurs from the least hindered side of the steroid to provide only the a-fluoro derivatives. The formation of rearrangement and elimination products supports the proposed mechanism for the DAST reaction. Reaction products are definitively characterized by one- and two-dimensional (1D and 2D) NMR methods.