9α,17α-Dihydroxy-3-methoxy-16β-methylandrosta-3,5-diene-17β-carbonitrile | 116256-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9α,17α-Dihydroxy-3-methoxy-16β-methylandrosta-3,5-diene-17β-carbonitrile
• 英文别名: 17-Beta-cyano-9-alpha,17-alpha-dihydroxy-3 methoxy-16-betamethylandrosta-3,5-diene；(8S,9R,10S,13S,14S,16S,17R)-9,17-dihydroxy-3-methoxy-10,13,16-trimethyl-2,7,8,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17-carbonitrile
• CAS: 116256-72-5
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: YKICFEOZAQDXBG-HJKAMDLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9α,17α-Dihydroxy-3-methoxy-16β-methylandrosta-3,5-diene-17β-carbonitrile 在 盐酸 、 异丙苯 、 碘 、 吡啶盐酸盐 、 calcium oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成
  参考文献：
  名称：

  Synthesis of corticoids from 9.alpha.-hydroxyandrost-4-ene-3,17-dione

  摘要：

  The synthesis of 17-alpha,21-bis(acetyloxy)-16-beta-methylpregna-4,9(11)-diene-3,20-dione (24) from the sterol-derived 9-alpha-hydroxyandrost-4-ene-3,17-dione (1) has been completed. The key steps in the synthesis are 16-beta-methylation and conversion of the 17-ketone to 17-beta-cyanohydrin 11. Elaboration of 11 to 9-alpha-hydroxy-16-beta-methylpregn-4-ene-3,20-dione (15) followed by 21-acetoxylation and simultaneous introduction of 9,11-unsaturation and 17-alpha-acetoxylation gave 24.

  DOI：

  10.1021/jo00029a032
• 作为产物：
  描述：

  9α-hydroxy-3-methoxy-3,5-androstenedione-17-one 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 9α,17α-Dihydroxy-3-methoxy-16β-methylandrosta-3,5-diene-17β-carbonitrile
  参考文献：
  名称：

  Synthesis of corticoids from 9.alpha.-hydroxyandrost-4-ene-3,17-dione

  摘要：

  The synthesis of 17-alpha,21-bis(acetyloxy)-16-beta-methylpregna-4,9(11)-diene-3,20-dione (24) from the sterol-derived 9-alpha-hydroxyandrost-4-ene-3,17-dione (1) has been completed. The key steps in the synthesis are 16-beta-methylation and conversion of the 17-ketone to 17-beta-cyanohydrin 11. Elaboration of 11 to 9-alpha-hydroxy-16-beta-methylpregn-4-ene-3,20-dione (15) followed by 21-acetoxylation and simultaneous introduction of 9,11-unsaturation and 17-alpha-acetoxylation gave 24.

  DOI：

  10.1021/jo00029a032

文献信息

• 9-alpha-hydroxy steroids, process for their preparation, process for the
  申请人：Gist-Brocades N.V.

  公开号：US05352809A1

  公开（公告）日：1994-10-04

  New 9-alphahydroxy steroids are prepared by the introduction of substituents on the D-ring of 9-alpha-hydroxy-androst-4-ene-3,17-dione. The resulting compounds are useful intermediates in the synthesis of corticosteroids.

  新的9-α-羟基类固醇是通过在9-α-羟基雄烯二酮-3,17-二烯的D环上引入取代基而制备的。所得化合物是合成皮质类固醇中有用的中间体。
• 9-alpha-hydroxysteroids, process for their preparation and process for the preparation of the corresponding 9(11)-dehydro-derivatives.
  申请人：ROUSSEL-UCLAF

  公开号：EP0263569B1

  公开（公告）日：1992-12-09
• PROCESS FOR DEHYDRATING CORTICOSTEROID INTERMEDIATES
  申请人：SCHERING CORPORATION

  公开号：EP0502112A1

  公开（公告）日：1992-09-09
• US5352809A
  申请人：——

  公开号：US5352809A

  公开（公告）日：1994-10-04
• US5565588A
  申请人：——

  公开号：US5565588A

  公开（公告）日：1996-10-15