11alpha,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 | 85700-75-0

• 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: 11alpha,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮
• 英文名称: 16β-methyl-11β,17,α21-trihydroxypregna-1,4-diene-3,20-dione
• 英文别名: 11alpha,17,21-Trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione；(8S,9S,10R,11R,13S,14S,16S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 85700-75-0
• 化学式: C₂₂H₃₀O₅
• 分子量: 374.477
• InChiKey: WNYLPFCKNQAAMB-OWUXUVPTSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11alpha,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 在 吡啶 、 高氯酸 、 1,3-二溴-5,5-二甲基海因 、 五氯化磷 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 倍他米松环氧水解物
  参考文献：
  名称：

  Process Improvements in the Synthesis of Corticosteroid 9,11β-Epoxides

  摘要：

  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.

  DOI：

  10.1021/op0102013

文献信息

• ——
  作者：WLODARCZYK S.、 FLORCZAK T.、 KORBEL J.、 LUBISZ K.

  DOI：——

  日期：——
• SKIBINSKA, MARIA;SMOLINSKA, JADWIGA;MALINOWSKA, MARIA, ACTA POL. PHARM., 44,(1987) N 6, 509-513
  作者：SKIBINSKA, MARIA、SMOLINSKA, JADWIGA、MALINOWSKA, MARIA

  DOI：——

  日期：——
• 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.