17-Oxo-3β-hydroxyestra-1(10),5-diene | 843-81-2

• 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: 17-Oxo-3β-hydroxyestra-1(10),5-diene
• 英文别名: 3β-Hydroxy-19-norandrosta-1(10),5-dien-17-one；3β-Hydroxyoestra-1(10),5-dien-17-on；(3S,8R,9S,13S,14S)-3-hydroxy-13-methyl-3,4,7,8,9,11,12,14,15,16-decahydro-2H-cyclopenta[a]phenanthren-17-one
• CAS: 843-81-2
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: BXWICSIYVFYHOU-CWLUVXEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  17-Oxo-3β-hydroxyestra-1(10),5-diene 在 N-甲基-4-哌啶酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以77%的产率得到雌酚酮
  参考文献：
  名称：

  Stereoelectronically Controlled, Thallium(III)-Mediated C-19 Degradation of 19-Hydroxy Steroids. An Expedient Route to Estrone and its Congeners via 19-Nor-10.beta.-hydroxy Intermediates

  摘要：

  Estrone- (8b) has been synthesized in four steps from 3 beta-acetoxy-19-hydroxyandrost-5-en-17-one (2b), readily available from an industrial precursor. A key feature of the strategy is a stereoelectronically controlled, TI(III)-mediated degradation (2b --> 5b). Oppenauer oxidation of diol 6b, resulting from saponification of the acetate 5b, afforded the unsaturated 10 beta-hydroxy ketone 7b, acid treatment of which induced aromatization affording 8b. An alternative route including dehydration (5b --> 9b) followed by Oppenauer oxidation (10b --> 8b) gave comparable results. This strategy has first been developed with the aid of cholestane model compounds (2a --> 5a) and then successfully applied to the synthesis of analogues in the cholestane, androstane, and pregnane series to produce the corresponding 19-nor-10 beta-hydroxy derivatives 7a-d and A-aromatic steroids 8a-d.

  DOI：

  10.1021/jo00097a056
• 作为产物：
  描述：

  3β,19-dihydroxy-5-androsten-17-one 生成 17-Oxo-3β-hydroxyestra-1(10),5-diene
  参考文献：
  名称：

  Mickova,R.; Syhora,K., Collection of Czechoslovak Chemical Communications, 1969, vol. 34, p. 458 - 467

  摘要：

  DOI：

文献信息

• Suginome, Hiroshi; Senboku, Hisanori; Yamada, Shinji, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2199 - 2205
  作者：Suginome, Hiroshi、Senboku, Hisanori、Yamada, Shinji

  DOI：——

  日期：——
• SUGINOME, HIROSHI;SENBOKU, HISANORI;YAMADA, SHINJI, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 2199-2205
  作者：SUGINOME, HIROSHI、SENBOKU, HISANORI、YAMADA, SHINJI

  DOI：——

  日期：——
• Stereoelectronically Controlled, Thallium(III)-Mediated C-19 Degradation of 19-Hydroxy Steroids. An Expedient Route to Estrone and its Congeners via 19-Nor-10.beta.-hydroxy Intermediates
  作者：Pavel Kocovsky、Richard S. Baines

  DOI：10.1021/jo00097a056

  日期：1994.9

  Estrone- (8b) has been synthesized in four steps from 3 beta-acetoxy-19-hydroxyandrost-5-en-17-one (2b), readily available from an industrial precursor. A key feature of the strategy is a stereoelectronically controlled, TI(III)-mediated degradation (2b --> 5b). Oppenauer oxidation of diol 6b, resulting from saponification of the acetate 5b, afforded the unsaturated 10 beta-hydroxy ketone 7b, acid treatment of which induced aromatization affording 8b. An alternative route including dehydration (5b --> 9b) followed by Oppenauer oxidation (10b --> 8b) gave comparable results. This strategy has first been developed with the aid of cholestane model compounds (2a --> 5a) and then successfully applied to the synthesis of analogues in the cholestane, androstane, and pregnane series to produce the corresponding 19-nor-10 beta-hydroxy derivatives 7a-d and A-aromatic steroids 8a-d.
• Mickova,R.; Syhora,K., Collection of Czechoslovak Chemical Communications, 1969, vol. 34, p. 458 - 467
  作者：Mickova,R.、Syhora,K.

  DOI：——

  日期：——