(16beta)-17,21-二羟基-16-甲基孕甾-1,4,9(11)-三烯-3,20-二酮 | 13504-15-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: (16beta)-17,21-二羟基-16-甲基孕甾-1,4,9(11)-三烯-3,20-二酮
• 中文别名: 倍他米松EP杂质C
• 英文名称: 17α,21-dihydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione
• 英文别名: 17α-Hydroxy-21-hydroxypregna-4,9(11)-diene-3,20-dione；17α,21-Dihydroxy-16β-methylpregna-1,4,9(11)-triene 3,20-dione；17α,21-dihydroxy-16β-methylpregna-1,4,9(11)-trien-3,20-dione；17,21-Dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione；(8S,10S,13S,14S,16S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 13504-15-9
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: ZYTXTXAMMDTYDQ-AKXKBWEISA-N

物化性质

• 熔点：
  209-212 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  548.3±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (16beta)-17,21-二羟基-16-甲基孕甾-1,4,9(11)-三烯-3,20-二酮 在 potassium bromate 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 以99.1%的产率得到(8S,9R,10S,11S,13S,14S,16S,17R)-9-bromo-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  甾体化合物9位上氟的方法和应用

  摘要：

  本发明提供一种甾体化合物9位上氟的方法和应用，涉及化学合成技术领域。本发明以式I化合物为起始原料，与第一溴化试剂、第二溴化试剂和盐酸发生9,11位溴羟反应得到式II化合物，式II化合物与氟试剂发生9位置换反应，得到9位氟代甾体化合物。本发明反应条件温和，避免高氯酸、氟化氢溶液等高毒性、强腐蚀性的试剂，对环境友好，路线短，便于操作，更适合工业化生产。

  公开号：

  CN114685592A
• 作为产物：
  描述：

  (16beta)-17-羟基-16-甲基-3,20-二氧代孕甾烷-1,4,9(11)-三烯-21-基苯甲酸酯 生成 (16beta)-17,21-二羟基-16-甲基孕甾-1,4,9(11)-三烯-3,20-二酮
  参考文献：
  名称：

  AYER, D. E.;SCHLAGEL, C. A.

  摘要：

  DOI：

文献信息

• 17.alpha.-Acyloxy-5.beta.-corticoids
  申请人：The Upjohn Company

  公开号：US04336200A1

  公开（公告）日：1982-06-22

  17.alpha.-Acyloxy-5.beta.-pregnanes (I) and 17.alpha.-acyloxy-5.alpha.-pregnanes (IV) have an excellent activity split providing high topical antiinflammatory activity with very low systemic side effects.

  17α-酰氧基-5β-孕烷(I)和17α-酰氧基-5α-孕烷(IV)具有出色的活性分离，提供高效的局部抗炎活性，且系统副作用非常低。
• 17-Alpha ethynyl steroids
  申请人：THE UPJOHN COMPANY

  公开号：EP0402963A2

  公开（公告）日：1990-12-19

  A 17α-ethynyl steroid selected from the group consisting of 17α-­ethynyl-3,17β-dihydroxy-16β-methylandrosta-3,5-diene 3-methyl ether, 17α-ethynyl-3,17β-dihydroxy-16β-methylandrost-5-ene 3-THP ether, 17α-­ethynyl-3,17β-dihydroxy-16β-methylandrosta-3,5,9(11)-triene 3-methyl ether, 17α-ethynyl-17β-hydroxy-16β-methylandrost-4-en-3-one, 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-4,9(11)-dien-3-one, and 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-1,4,9(11)-trien-3-one.

  一种 17α-乙炔类固醇，选自以下组别：17α-乙炔基-3,17β-二羟基-16β-甲基雄甾-3,5-二烯 3-甲醚、17α-乙炔基-3,17β-二羟基-16β-甲基雄甾-5-烯 3-THP醚、17α-乙炔基-3,17β-二羟基-16β-甲基雄甾-3、5,9(11)-triene 3-methyl ether, 17α-ethynyl-17β-hydroxy-16β-methylandrost-4-en-3-one, 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-4,9(11)-dien-3-one, and 17α-­ethynyl-17β-hydroxy-16β-methylandrosta-1,4,9(11)-trien-3-one.
• Catalytic Epoxidation of Alkenes with Oxone
  作者：Scott E. Denmark、David C. Forbes、David S. Hays、Jeffrey S. DePue、Richard G. Wilde

  DOI：10.1021/jo00110a049

  日期：1995.3

  A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96% yield.
• Process Improvements in the Synthesis of Corticosteroid 9,11β-Epoxides
  作者：Xiaoyong Fu、Chou-Hong Tann、T. K. Thiruvengadam

  DOI：10.1021/op0102013

  日期：2001.7.1

  Corticosteroid 9,11 beta -epoxides are key intermediates in the preparation of pharmaceutically important compounds such as betamethasone, mometasone, beclomethasone, and dexamethasone. A new process for the 9,11 beta -epoxide was developed using a PCl5-mediated regioselective dehydration of II alpha -hydroxysteroid to form the corresponding Delta (9,11) double bond. The olefin is then converted into 9 alpha ,11 beta -bromoformate by treatment with 1,3-dibromo-5, 5-dimethyl hydantoin (DBH) in DMF and subsequently cyclized to produce the desired 9,11 beta -epoxide upon treatment with NaOH. Major process-related impurities such as 21-OH-Delta (9,11)-triene, 21-OH-Delta (11,12)-triene, 21-Cl-Delta (9,11)-triene, and beta -epoxide-21-cathylate as well as 11 beta -Cl are all eliminated or minimized. This new process has been implemented in our manufacturing facility in full-scale production and proved to raise the overall yield and the quality of the product dramatically compared to the existing process.
• Stabilised monolithium acetylide and the ethynylation of steroids
  申请人：THE UPJOHN COMPANY

  公开号：EP0148616B1

  公开（公告）日：1991-04-17