3β-acetoxy-14-hydroxy-5β,14β-androst-15-en-17-one | 111119-42-7

• 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: 3β-acetoxy-14-hydroxy-5β,14β-androst-15-en-17-one
• 英文别名: 3β-acetoxy-14β-hydroxy-5β-androst-15-en-17-one；3beta-Acetoxy-14beta-hydroxy-5beta-androst-15-en-17-one；[(3S,5R,8R,9S,10S,13S,14S)-14-hydroxy-10,13-dimethyl-17-oxo-2,3,4,5,6,7,8,9,11,12-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 111119-42-7
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: QKAWBGSOTHUFDR-QLPFELHZSA-N

物化性质

• 沸点：
  466.8±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-14-hydroxy-5β,14β-androst-15-en-17-one 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3β-Acetoxy-14-hydroxy-5β,14β-androstan-17-on
  参考文献：
  名称：

  Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

  摘要：

  Two methods have been developed for efficient conversion of pregna-14,16-dien-20-ones into 14beta-hydroxyandrost-15-en-17-ones. One procedure consists of treatment of the ring-D dienone successively with sodium borohydride and singlet oxygen. The reaction is illustrated by the conversion of pregna-14,16-dien-20-one 1 into 14beta-hydroxyandrost-15-en-17-one 3, via the corresponding allylic alcohol 2. Although this two-step procedure is simple, it provides 3 in relatively low yield, accompanied by a smaller amount of the isomeric 14alpha-hydroxyandrost-15-en-17-one 6. An alternative one-step conversion is achieved by treatment of dienone 1 with a peroxyacid in the presence of a strong protic acid. This process is illustrated by the two-step conversion of dienone I into hydroxy ketone 11 in 51% overall yield (Scheme 5) and by the analogous conversion of dienone 13 into hydroxy ketone 24 in 61% overall yield (Scheme 11).

  DOI：

  10.1021/jo011175+
• 作为产物：
  描述：

  3b-羟基-5b-孕甾-16-烯-20-酮乙酸酯 在 N-溴代丁二酰亚胺(NBS) 、 甲烷磺酸 、 偶氮二异丁腈 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 10.0h， 生成 3β-acetoxy-14-hydroxy-5β,14β-androst-15-en-17-one
  参考文献：
  名称：

  Oxidative Fragmentation of Pregna-14,16-dien-20-ones to 14β-Hydroxyandrost-15-en-17-ones

  摘要：

  Two methods have been developed for efficient conversion of pregna-14,16-dien-20-ones into 14beta-hydroxyandrost-15-en-17-ones. One procedure consists of treatment of the ring-D dienone successively with sodium borohydride and singlet oxygen. The reaction is illustrated by the conversion of pregna-14,16-dien-20-one 1 into 14beta-hydroxyandrost-15-en-17-one 3, via the corresponding allylic alcohol 2. Although this two-step procedure is simple, it provides 3 in relatively low yield, accompanied by a smaller amount of the isomeric 14alpha-hydroxyandrost-15-en-17-one 6. An alternative one-step conversion is achieved by treatment of dienone 1 with a peroxyacid in the presence of a strong protic acid. This process is illustrated by the two-step conversion of dienone I into hydroxy ketone 11 in 51% overall yield (Scheme 5) and by the analogous conversion of dienone 13 into hydroxy ketone 24 in 61% overall yield (Scheme 11).

  DOI：

  10.1021/jo011175+

文献信息

• 17-Aryl and 17-heterocyclyl-5.beta.,14.beta.-androstane derivatives
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：US05567694A1

  公开（公告）日：1996-10-22

  17-aryl and heterocyclyl-5.beta.,14.beta.-androstane compounds having the formula (I) ##STR1## wherein R is an aryl ring or a saturated or unsaturated heterocyclic ring are active on the cardiovascular system and are useful in treating cardiovascular disorders.

  具有以下式(I)的17-芳基和杂环基-5.beta.,14.beta.-雄甾烷化合物：##STR1## 其中R为芳基环或饱和或不饱和的杂环环，对心血管系统具有活性并且在治疗心血管疾病方面有用。
• Groszek, Grazyna; Kabat, Marek M.; Kurek, Alicja, Bulletin of the Polish Academy of Sciences: Chemistry, 1986, vol. 34, # 7-8, p. 313 - 320
  作者：Groszek, Grazyna、Kabat, Marek M.、Kurek, Alicja、Masnyk, Marek、Wicha, Jerzy

  DOI：——

  日期：——
• 17B-Aryl and 17B-heterocyclyl-5-beta,14-beta-andostane derivatives active on the cardiovascular system, processes for their preparation and pharmaceutical compositions containing same
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0590272B1

  公开（公告）日：1997-01-02
• US5567694A
  申请人：——

  公开号：US5567694A

  公开（公告）日：1996-10-22