3α,5-cyclo-5α-androstane-6α,17β-diol | 78964-13-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3α,5-cyclo-5α-androstane-6α,17β-diol
• 英文别名: 6α,17β-dihydroxy-3α,5-cycloandrostane；(1S,2R,5R,7R,8S,10R,11S,14S,15S)-2,15-dimethylpentacyclo[8.7.0.02,7.05,7.011,15]heptadecane-8,14-diol
• CAS: 78964-13-3
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: XPHGBPFEVNHDGX-OPVHSXAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3α,5-cyclo-5α-androstane-6α,17β-diol 在 fungus Aspergillus tamarii KITA (QM 1223) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以21%的产率得到6α-hydroxy-17α-oxa-D-homo-3α,5-cycloandrostane-17-one
  参考文献：
  名称：

  Metabolic fate of 3α,5-cycloandrostanes in the endogenous lactonization pathway of Aspergillus tamarii KITA

  摘要：

  A series of 3 alpha,5-cycloandrostane analogues with a range of functionality (6 alpha and 6 beta alcohols and ketone) at carbon 6 were tested in the endogenous lactonization pathway in Aspergillus tamarii KITA. This metabolic route converts progesterone to testololactone in high yield through a four step enzymatic pathway. To date, no studies have looked at the effect of steroids devoid of polar functionality at carbon 3 and their subsequent metabolic fate by fungi which contain Baeyer-Villiger monooxygenases. Incubation of all of the cycloandrostane analogues resulted in lactonization of ring-D irrespective of C-6 stereochemistry or absence of C-3 functionality. Presence of 6 beta-hydroxy group and the C-17 ketone was required in order for these analogues to undergo hydroxylation at C-15 beta position. All metabolites were isolated by column chromatography and were identified by H-1, C-13 NMR, DEPT analysis and other spectroscopic data. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2015.09.003
• 作为产物：
  描述：

  去氢表雄酮 在 吡啶 、 sodium tetrahydroborate 、 Jones reagent 、 甲基磺酰氯 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 21.17h， 生成 3α,5-cyclo-5α-androstane-6α,17β-diol
  参考文献：
  名称：

  Metabolic fate of 3α,5-cycloandrostanes in the endogenous lactonization pathway of Aspergillus tamarii KITA

  摘要：

  A series of 3 alpha,5-cycloandrostane analogues with a range of functionality (6 alpha and 6 beta alcohols and ketone) at carbon 6 were tested in the endogenous lactonization pathway in Aspergillus tamarii KITA. This metabolic route converts progesterone to testololactone in high yield through a four step enzymatic pathway. To date, no studies have looked at the effect of steroids devoid of polar functionality at carbon 3 and their subsequent metabolic fate by fungi which contain Baeyer-Villiger monooxygenases. Incubation of all of the cycloandrostane analogues resulted in lactonization of ring-D irrespective of C-6 stereochemistry or absence of C-3 functionality. Presence of 6 beta-hydroxy group and the C-17 ketone was required in order for these analogues to undergo hydroxylation at C-15 beta position. All metabolites were isolated by column chromatography and were identified by H-1, C-13 NMR, DEPT analysis and other spectroscopic data. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2015.09.003

文献信息

• Reduction of steroidal dicarbonyl compounds with poly(n-isopropyliminoalane)
  作者：M.Paglialunga Paradisi、G.Pagani Zecchini

  DOI：10.1016/s0040-4020(01)97670-7

  日期：1981.1