9α-Hydroxy-3-methoxy-16β-methylandrosta-3,5-dien-17-one | 116256-33-8

• 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: 9α-Hydroxy-3-methoxy-16β-methylandrosta-3,5-dien-17-one
• 英文别名: 9-alpha-hydroxy-3-methoxy-16-beta-methylandrosta-3,5-dien-17-one；9α-hydroxy-3-methoxy-16β-methylandrost-3,5-dien-17-one；9alpha-Hydroxy-3-methoxy-16beta-methylandrost-3,5-dien-17-one；(8S,9R,10S,13S,14S,16S)-9-hydroxy-3-methoxy-10,13,16-trimethyl-2,7,8,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 116256-33-8
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: CZWBLBOFOLAIMK-FVWCLLPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9α-Hydroxy-3-methoxy-16β-methylandrosta-3,5-dien-17-one 在 盐酸 、 异丙苯 、 溴 、 吡啶盐酸盐 、 potassium hydrogencarbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 21-Bromo-9α,17α-dihydroxy-16β-methylpregn-4-ene-3,20-dione
  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：

  9-alpha-hydroxy-3-methoxy-16-methylene-androsta-3,5-dien-17-one 在 钯 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 9α-Hydroxy-3-methoxy-16β-methylandrosta-3,5-dien-17-one
  参考文献：
  名称：

  9-alpha-hydroxy steroids, process for their preparation, process for the

  摘要：

  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。

  公开号：

  US05352809A1

文献信息

• A corticoid synthesis from 9α-hydroxyandrost-4-ene-3,17-dione via a steroidal allene
  作者：David R. Andrews、Robert A. Giusto、Anantha R. Sudhakar

  DOI：10.1016/0040-4039(96)00583-7

  日期：1996.5

  An alternative synthesis of 17α, 21-dihydroxy-16β-methylpregna-4,9(11)-diene-3,20-dione, an intermediate to the potent anti-inflammatory corticoid, Betamethasone, is described. The key reactions are the bis epoxidation of a C-17,20 allene and the regiospecific elimination of a 9α-methyl carbonate.

  描述了一种强力消炎皮质类固醇倍他米松的中间体17α，21-二羟基-16β-甲基孕烯-4,9（11）-二烯-3,20-二酮的替代合成方法。关键反应是C-17,20丙二烯的双环氧化和9α-甲基碳酸酯的区域特异性消除。
• Steroid intermediates and processes for their preparation
  申请人：Schering Corporation

  公开号：US05502183A1

  公开（公告）日：1996-03-26

  Novel steroids having a 9.alpha.-hydroxy or a 9.alpha.-carbonate substituent can be prepared from 9.alpha.-hydroxyandrostenedione and can be utilized in the synthesis of commercially valuable corticosteroids such as betamethasone. The 9.alpha.-carbonates are prepared by reaction of the corresponding 9.alpha.-hydroxy steroid with a sequence of excess base, trialkylsilyl chloride, alkyl haloformate and alkanol or by using excess base, alkyl haloformate and alkoxide. 9.alpha.-Carbonate-17-keto compounds can be treated with lithium acetylide and a lithium salt to afford the corresponding 17.alpha.-ethynyl-17.beta.-hydroxy-9.alpha.-carbonate. This compound is then esterified with a novel series of reagents to give the 17-ester which can be reduced the corresponding 17-allene. Oxidation of this allene to the bis-epoxide compound, followed by treatment with an alkali metal salt of a carboxylic acid under phase transfer conditions gives the 17.alpha.-hydroxy 21-ester 9.alpha.-carbonate. Elimination of the 9.alpha.-carbonate group affords the a 17.alpha.-hydroxy, 9(11)ene, which in a few subsequent steps can be converted to a variety of commercially important corticosteroids. Novel 9.alpha.-carbonate compounds are prepared in the various reaction steps.

  新型类固醇具有9.alpha.-羟基或9.alpha.-碳酸酯取代基，可以从9.alpha.-羟基雄烯二酮中制备，并可用于合成商业上有价值的皮质类固醇，如倍他米松。9.alpha.-碳酸酯可通过相应的9.alpha.-羟基类固醇与过量碱、三烷基氯硅烷、烷基卤酸酯和烷醇的反应序列，或者通过使用过量碱、烷基卤酸酯和碱性氧化物来制备。9.alpha.-碳酸酯-17-酮化合物可与锂乙炔和锂盐反应，以得到相应的17.alpha.-乙炔基-17.beta.-羟基-9.alpha.-碳酸酯。然后，将这种化合物与新型系列试剂酯化，得到17-酯，可以还原为相应的17-烯基。将这种烯基氧化为双环氧化合物，然后在相转移条件下用羧酸的碱金属盐处理，得到17.alpha.-羟基21-酯9.alpha.-碳酸酯。消除9.alpha.-碳酸酯基团得到17.alpha.-羟基，9(11)烯，经过几个步骤可转化为各种商业重要的皮质类固醇。在各种反应步骤中制备新型9.alpha.-碳酸酯化合物。
• 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
• NOVEL STEROID INTERMEDIATES AND PROCESSES FOR THEIR PREPARATION
  申请人：SCHERING CORPORATION

  公开号：EP0624162B1

  公开（公告）日：1998-09-16
• US5352809A
  申请人：——

  公开号：US5352809A

  公开（公告）日：1994-10-04