4α-benzylthio-19-hydroxy-5α-androstane-3,6,17-trione | 152952-75-5

• 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: 4α-benzylthio-19-hydroxy-5α-androstane-3,6,17-trione
• CAS: 152952-75-5
• 化学式: C₂₆H₃₂O₄S
• 分子量: 440.604
• InChiKey: CZGYDOHVUFMIIF-CEVDJHOKSA-N

物化性质

• 沸点：
  628.6±55.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  4α-benzylthio-19-hydroxy-5α-androstane-3,6,17-trione 在 Ra-Ni 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 3β,19-dihydroxy-5α-androstane-6,17-dione
  参考文献：
  名称：

  1,4-Addition reaction with thiols and conformational analysis with PM3 molecular orbital calculations of 19-oxygenated androst-4-ene-3,6,17-triones

  摘要：

  Reactions of androst4-ene-3,6,17-trione (1) and its 19-hydroxy or 19-oxo derivative (2 or 3), suicide substrates of aromatase, with thiols were initially studied. Treatment of 4-ene-3,6-diones 1-3 with benzyl-mercaptan in MeOH at room temperature gave the corresponding 4alpha-benzylthio-5alpha-androstane-3,6-diones (4-6) as the major products in 24-80% yields. The C18 steroid, estr-5(10)-ene-3,6,17-trione (7), was also isolated on the treatment of 19-oxo steroid 3. Oxidation with NaIO4 and reduction with Raney Ni of the adducts gave the corresponding 4-ene-3,6-dione and desulfurized products, respectively. The results show that 19-oxygenated steroids 2 and 3 react with a thiol in a 1,4-addition manner. By means of PM3 molecular orbital calculations, the conformational features of the 19-oxygen functions of 4-ene-3,6-diones 2 and 3, 5alpha-3,6-diones 10 and 11, and their 4alpha-methylthio derivatives 14 and 15, model compounds of 1,4-adducts 5 and 6, were determined. In the compounds examined, the 19-hydroxy steroids favor a conformation having the hydroxyl group above the A-ring, whereas the 19-oxo substituent is oriented in the out-of-ring position (not above either A- or B-ring). These calculations suggest that compound 1 would inactivate aromatase by the same steric course of the oxygenation at C-19 as that of the natural substrate, androstenedione.

  DOI：

  10.1016/0039-128x(93)90082-x
• 作为产物：
  描述：

  苄硫醇 、 19-hydroxy-androst-4-ene-3,6,17-one 以 甲醇 为溶剂， 反应 8.0h， 以57%的产率得到4α-benzylthio-19-hydroxy-5α-androstane-3,6,17-trione
  参考文献：
  名称：

  1,4-Addition reaction with thiols and conformational analysis with PM3 molecular orbital calculations of 19-oxygenated androst-4-ene-3,6,17-triones

  摘要：

  Reactions of androst4-ene-3,6,17-trione (1) and its 19-hydroxy or 19-oxo derivative (2 or 3), suicide substrates of aromatase, with thiols were initially studied. Treatment of 4-ene-3,6-diones 1-3 with benzyl-mercaptan in MeOH at room temperature gave the corresponding 4alpha-benzylthio-5alpha-androstane-3,6-diones (4-6) as the major products in 24-80% yields. The C18 steroid, estr-5(10)-ene-3,6,17-trione (7), was also isolated on the treatment of 19-oxo steroid 3. Oxidation with NaIO4 and reduction with Raney Ni of the adducts gave the corresponding 4-ene-3,6-dione and desulfurized products, respectively. The results show that 19-oxygenated steroids 2 and 3 react with a thiol in a 1,4-addition manner. By means of PM3 molecular orbital calculations, the conformational features of the 19-oxygen functions of 4-ene-3,6-diones 2 and 3, 5alpha-3,6-diones 10 and 11, and their 4alpha-methylthio derivatives 14 and 15, model compounds of 1,4-adducts 5 and 6, were determined. In the compounds examined, the 19-hydroxy steroids favor a conformation having the hydroxyl group above the A-ring, whereas the 19-oxo substituent is oriented in the out-of-ring position (not above either A- or B-ring). These calculations suggest that compound 1 would inactivate aromatase by the same steric course of the oxygenation at C-19 as that of the natural substrate, androstenedione.

  DOI：

  10.1016/0039-128x(93)90082-x