17α-hydroxy-3-oxo-4-androstene-17-carboxylic acid amide | 81481-39-2

• 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-hydroxy-3-oxo-4-androstene-17-carboxylic acid amide
• 英文别名: 17alpha-Hydroxy-3-oxo-4-androstene-17-carboxylic acid amide；(8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• CAS: 81481-39-2
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: FLDLNSLCFAAMKN-VRYCVARASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17α-hydroxy-3-oxo-4-androstene-17-carboxylic acid amide 在 palladium on activated charcoal 乙酸铵 、 potassium permanganate 、 sodium periodate 、 氯化亚砜 、 硫酸 、 氢气 、 sodium carbonate 、 sodium nitrite 作用下， 以 吡啶 、 水 、 溶剂黄146 、 甲苯 、 叔丁醇 为溶剂， 5.0~50.0 ℃ 、1.0 MPa 条件下， 反应 16.75h， 生成 N-(3'-trifluoromethyl-4'-aminophenyl)-17α-hydroxy-3-oxo-4-azaandrost-5-ene-17β-carboxamide
  参考文献：
  名称：

  Synthesis of N-Substituted 3-Oxo-17b- carboxamide-4-aza-5a-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes

  摘要：

  An N-aryl-3-oxo-4-aza-5 alpha-androst-1-ene-17 beta-carboxamide and three N-aryl or alkyl substituted 17 alpha-hydroxy-3-oxo-4-aza-5 alpha -androstane-17 beta-carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17 beta-carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.

  DOI：

  10.3987/com-97-s(n)35
• 作为产物：
  描述：

  表雄酮 在 氢氧化钾 、 高氯酸 、 乙酸酐 作用下， 以 甲醇 、 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 溶剂黄146 为溶剂， 生成 17α-hydroxy-3-oxo-4-androstene-17-carboxylic acid amide
  参考文献：
  名称：

  Process for the preparation of 17.alpha.-hydroxy- and

  摘要：

  该公式表示的17.alpha.-羟基和17a.alpha.-羟基-D-同型硫代羧酸，其中n为1或2，A为，R.sub.1为H或CH.sub.3，通过在高氯酸存在下用混合物水合对应的17-腈进行制备。然后，将产生的17.beta.-N-酰基羧酰胺在多元醇中用碱金属氢氧化物在高温下进行处理。这些产物酸是中间体，例如用于生产具有抗炎活性的类固醇。

  公开号：

  US04348327A1

文献信息

• Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2', 4' -diones from 17-keto steroids
  作者：Mauro Ginanneschi、Mario Chelli、Annamaria Papini、Gianfranco Rapi

  DOI：10.1016/0039-128x(90)90088-s

  日期：1990.11

  Spiro[androst-4-en-17alpha, 5'-oxazolidine]-2', 3, 4'-trione 8-alpha and spiro]androst-4-en-17alpha, 5'-oxazolidine[-2', 3, 4', 11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64% and 49.5% yield, respectively). The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkychlorocarbonates. The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF. A new method for the synthesis of steroid 17-alpha-hydroxy-17-carboxyesters and 17-alpha-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful.
• US4348327A
  申请人：——

  公开号：US4348327A

  公开（公告）日：1982-09-07