17aα-methyl-17-oxa-D-homo-1,4-androstadien-3,16-dione | 849425-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 17aα-methyl-17-oxa-D-homo-1,4-androstadien-3,16-dione
• 英文别名: (1S,4aS,4bR,10aR,10bS,12aS)-1,10a,12a-trimethyl-4,4a,4b,5,6,10b,11,12-octahydro-1H-naphtho[2,1-f]isochromene-3,8-dione
• CAS: 849425-38-3
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: UQIIGZCLFUBGLA-JHXXRYTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17aα-methyl-17-oxa-D-homo-1,4-androstadien-3,16-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以52%的产率得到17aα-methyl-17-oxa-D-homo-1,4,6-androstatrien-3,16-dione
  参考文献：
  名称：

  Synthesis and anti-aromatase activity of some new steroidal D-lactones

  摘要：

  Starting from D-seco derivatives of 5-androstene 1-3, the D-homo lactones, 4 and 5, were synthesized. By the Oppenauer oxidation and/or by dehydration of 4 and 5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or 2,3,5,6-tetrachloro-1,4-betizoquinone (chloranil), the corresponding D-lactones 6-12 were obtained. The structures of 6 and 10 were unambiguously proved by the appropriate X-ray structural analysis. Anti-aromatase assay showed that tested compounds possess inhibition potency, however. two to four times smaller (IC50 from 0.2 to 0.7 mum, respectively) in comparison to aminoglutethimide (AG). (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.10.005
• 作为产物：
  描述：

  17aα-methyl-17-oxa-D-homo-4-androsten-3,16-dione 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以60%的产率得到17aα-methyl-17-oxa-D-homo-1,4-androstadien-3,16-dione
  参考文献：
  名称：

  Synthesis and anti-aromatase activity of some new steroidal D-lactones

  摘要：

  Starting from D-seco derivatives of 5-androstene 1-3, the D-homo lactones, 4 and 5, were synthesized. By the Oppenauer oxidation and/or by dehydration of 4 and 5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or 2,3,5,6-tetrachloro-1,4-betizoquinone (chloranil), the corresponding D-lactones 6-12 were obtained. The structures of 6 and 10 were unambiguously proved by the appropriate X-ray structural analysis. Anti-aromatase assay showed that tested compounds possess inhibition potency, however. two to four times smaller (IC50 from 0.2 to 0.7 mum, respectively) in comparison to aminoglutethimide (AG). (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.10.005