des-A,B-androstan-8-one | 881182-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: des-A,B-androstan-8-one
• 英文别名: (3aR,7aS)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 881182-36-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: FFUDPYOCQXOTSL-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  des-A,B-androstan-8-one 在 palladium on activated charcoal 咪唑 、 六甲基磷酰三胺 、 重铬酸吡啶 、 lithium diethylamide 、 氢气 、 sodium naphthalenide 、 二异丁基氢化铝 、 三乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.08h， 生成 8β-tert-butyldimethylsilyloxy-des-A,B-androstan-12-one
  参考文献：
  名称：

  Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12

  摘要：

  The plethora of actions of 1 alpha,25(OH)(2)D-3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of the natural ligand. In light of the crystal structures of the vitamin D nuclear receptor (VDR), novel analogues of the hormone 1 alpha,25(OH)2D3 with side chains attached to C-12 were synthesized via the convergent Wittig-Horner approach. Among the compounds studied, the analogue 2b showed the highest binding affinity for VDR and was the most potent at inducing VDR transcriptional activity in a transient transfection assay (20% of the transactivation activity of the natural ligand).

  DOI：

  10.1021/jm049016g
• 作为产物：
  描述：

  (3aR,4S,7aS)-7a-甲基八氢-1H-茚-4-醇 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以97%的产率得到des-A,B-androstan-8-one
  参考文献：
  名称：

  Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12

  摘要：

  The plethora of actions of 1 alpha,25(OH)(2)D-3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of the natural ligand. In light of the crystal structures of the vitamin D nuclear receptor (VDR), novel analogues of the hormone 1 alpha,25(OH)2D3 with side chains attached to C-12 were synthesized via the convergent Wittig-Horner approach. Among the compounds studied, the analogue 2b showed the highest binding affinity for VDR and was the most potent at inducing VDR transcriptional activity in a transient transfection assay (20% of the transactivation activity of the natural ligand).

  DOI：

  10.1021/jm049016g

文献信息

• Novel method for the preparation of intermediates useful for the synthesis fo vitamin d analogues
  申请人：Hansen Torngaard Erik

  公开号：US20070135395A1

  公开（公告）日：2007-06-14

  The present invention relates to novel methods for the preparation of intermediates which are useful in the synthesis of cacipotriol. The present invention relates further to the use of intermediates produced with said methods for making calcipotriol or calcipotriol monohydrate.

  本发明涉及一种新的方法，用于制备在合成卡西泊酯过程中有用的中间体。本发明进一步涉及使用采用上述方法制备的中间体来制备卡西泊酯或卡西泊酯一水合物。
• Conformational analysis and stability of substituted 4-hydrindanones. A thermodynamic and magnetic resonance (proton and carbon-13) study
  作者：Brigitte Lo Cicero、Feiga Weisbuch、Gilbert Dana

  DOI：10.1021/jo00318a017

  日期：1981.2
• NOVEL METHOD FOR THE PREPARATION OF INTERMEDIATES USEFUL FOR THE SYNTHESIS OF VITAMIN D ANALOGUES
  申请人：LEO PHARMA A/S

  公开号：EP1735276B1

  公开（公告）日：2011-02-16
• EPIMERISATION OF ALLYLIC ALCOHOLS
  申请人：LEO PHARMA A/S

  公开号：EP1789384B1

  公开（公告）日：2008-10-15
• METHODS FOR PRODUCING PARICALCITOL
  申请人：Azad Pharmaceutical Ingredients AG

  公开号：EP2334640B1

  公开（公告）日：2015-12-23