16α-bromo-3-methoxy-13α-estra-1,3,5(10)-triene-17-one | 25089-49-0

• 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: 16α-bromo-3-methoxy-13α-estra-1,3,5(10)-triene-17-one
• 英文别名: 3-Methoxy-16α-brom-13α-oestra-1,3,5(10)-trien-17-on；(8R,9S,13R,14S,16R)-16-bromo-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 25089-49-0
• 化学式: C₁₉H₂₃BrO₂
• 分子量: 363.294
• InChiKey: CSELWEPNDJXTQB-OGJJZOIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16α-bromo-3-methoxy-13α-estra-1,3,5(10)-triene-17-one 在 Pd/BaCO₃ lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 3-methoxy-13α-estra-1,3,5(10)-triene-17α-ol
  参考文献：
  名称：

  Nambara,T. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 11, p. 2366 - 2370

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基雌酮 在 溶剂黄146 、 邻苯二胺 、 copper(ll) bromide 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.5h， 生成 16α-bromo-3-methoxy-13α-estra-1,3,5(10)-triene-17-one
  参考文献：
  名称：

  Conformational Design for 13α-Steroids

  摘要：

  The diastereomeric 16-bromo- and 16-azido-17-alcohols 5-8, 11, 12, 16, and 17 and 17-ketones 3, 4, 9, and 10 of the 13 alpha-estra-1,3,5(10)-triene series were synthesized as precursors for biologically active compounds and chiral Ligands for metal complexation. Conformational investigations of these and some other compounds via X-ray analysis and H-1 NMR spectroscopy show the existence of compounds with the classical steroid conformation (ring C chair, restricted conformation of ring D) and such with an atypical ring C twist-boat and a flexible ring D conformation. It could be shown that 17 beta-substituents or flattening of the D-ring are responsible for the twist-boat conformation, whereas compounds containing a 17 alpha-substituent or 17 keto group possess the classical conformation. By varying the substituents, compounds with either of these conformations can be intentionally synthesized. MO calculations confirmed the relative stability of the twist-boat conformation.

  DOI：

  10.1021/jo000108x

文献信息

• Conformational Design for 13α-Steroids
  作者：Bruno Schönecker、Corinna Lange、Manuela Kötteritzsch、Wolfgang Günther、Jennie Weston、Ernst Anders、Helmar Görls

  DOI：10.1021/jo000108x

  日期：2000.9.1

  The diastereomeric 16-bromo- and 16-azido-17-alcohols 5-8, 11, 12, 16, and 17 and 17-ketones 3, 4, 9, and 10 of the 13 alpha-estra-1,3,5(10)-triene series were synthesized as precursors for biologically active compounds and chiral Ligands for metal complexation. Conformational investigations of these and some other compounds via X-ray analysis and H-1 NMR spectroscopy show the existence of compounds with the classical steroid conformation (ring C chair, restricted conformation of ring D) and such with an atypical ring C twist-boat and a flexible ring D conformation. It could be shown that 17 beta-substituents or flattening of the D-ring are responsible for the twist-boat conformation, whereas compounds containing a 17 alpha-substituent or 17 keto group possess the classical conformation. By varying the substituents, compounds with either of these conformations can be intentionally synthesized. MO calculations confirmed the relative stability of the twist-boat conformation.
• Nambara,T. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 11, p. 2366 - 2370
  作者：Nambara,T. et al.

  DOI：——

  日期：——