21-dehydrobudesonide | 85234-63-5

• 物质功能分类: 分析化学 - 对照品
• 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
• 英文名称: 21-dehydrobudesonide
• 英文别名: 9NI3N51Lfa；2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-9,13-dimethyl-16-oxo-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoacetaldehyde
• CAS: 85234-63-5
• 化学式: C₂₅H₃₂O₆
• 分子量: 428.525
• InChiKey: UHEOYIKQUMWUPY-KWVAZRHASA-N

物化性质

• 熔点：
  >110oC (dec.)
• 沸点：
  572.5±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)
• 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)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

制备方法与用途

用途

布地奈德为局部应用的不含卤素的肾上腺皮质激素类药物。临床研究证明吸入本品具有与倍氯米松相似的局部抗炎作用，而无全身肾上腺皮质激素作用。用于非激素依赖性或激素依赖性哮喘和哮喘性慢性支气管炎患者，可有效地减少口服肾上腺皮质激素的副作用。布地奈德杂质D为布地奈德制备过程中产生的杂质。

反应信息

• 作为产物：
  描述：

  左布地奈德 在 air 、 copper diacetate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以92%的产率得到21-dehydrobudesonide
  参考文献：
  名称：

  Air oxidation of 17-hydroxycorticosteroids catalyzed by cupric acetate: formation of hemiacetal dimers

  摘要：

  Hydrocortisone, cortexolone, hydrocortisone-17-butyrate, and budesonide were oxidized into alpha-ketoaldehydes by air exposure in the presence of Cu(OAc)(2). When free hydroxyl functions were present at position 17, hydrocortisone and cortexolone, the formed oxidation products, were identified as hemiacetal dimeric structures involving the free hydroxyl functions at position 17 and the newly formed aldehydes at position 21. Dimeric structures were established by using H-1{C-13} correlations (HSQC and HMBC) and H-1-H-1 correlations (COSY and ROESY). The hemiacetal function was further confirmed by reaction of the dimer formed from hydrocortisone with two equivalents of 3-methyl-2-benzotriazolinone hydrazine (MTBH), giving quantitatively two equivalents of the 3-methyl-2-benzotriazolinone hydrazone of 21-dehydrohydrocortisone. When no free hydroxyl function was present as in the case of hydrocortisone-17-butyrate and budesonide, the expected alpha-ketoaldehydes were obtained. (C) 2003 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(03)00033-3