A-norandrost-3(5)-ene-2,17-dione | 4060-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: A-norandrost-3(5)-ene-2,17-dione
• 英文别名: A-nor-androst-3-ene-2,17-dione；A-Nor-androst-3-en-2,17-dion；A-Nor-androst-3-en-2,17-dion；(3aR,3bS,5aS,8aS,8bR)-3a,5a-dimethyl-3,3b,4,5,7,8,8a,8b,9,10-decahydroindeno[5,4-e]indene-2,6-dione
• CAS: 4060-49-5
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: FZBASVPTMZVEBL-OIDVLUPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  0.78
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  A-norandrost-3(5)-ene-2,17-dione 在 溶剂黄146 、 锌 作用下， 生成 17α-Aethinyl-A-nortestosteron
  参考文献：
  名称：

  A-nor-5-alpha-雄烷衍生物。IV。具有潜在抗植入活性的新结构。

  摘要：

  DOI：

  10.1021/jm00303a011
• 作为产物：
  描述：

  A-nortestosterone 在 chromium(VI) oxide 作用下， 生成 A-norandrost-3(5)-ene-2,17-dione
  参考文献：
  名称：

  Synthesis of A-Norsteroids

  摘要：

  DOI：

  10.1021/ja01517a045

文献信息

• Microbial hydroxylation of steroids. Part 12. Hydroxylation of testosterone and related steroids by <i>Gnomonia</i><i>fructicola</i> ATCC 11430
  作者：Herbert L. Holland、Frances M. Brown、P. Chinna Chenchaiah、Michael J. Chernishenko、Shaheer H. Khan、J. Appa Rao

  DOI：10.1139/v89-044

  日期：1989.2.1

  The fungus Gnomoniafructicola ATCC 11430 hydroxylates testosterone at C-2β in 40–60% yield. The enzyme involved has been shown to be an inducible CO sensitive, cyanide insensitive oxygenase, with a requirement for theΔ⁴-3-ketosteroid substrate functionality. The use of 2α- and 2β-deuterium labelled substrates has shown that hydrogen loss from C-2 during 2β hydroxylation is isotope dependent and non-stereospecific. This is interpreted in terms of a Δ^2,4-dienolic enzyme-bound intermediate form of the substrate. Keywords: Gnomoniafructicola, hydroxylation, steroids, testosterone.

  真菌Gnomoniafructicola ATCC 11430以40-60%的产率在C-2β处对睾酮进行羟基化。所涉及的酶已被证明是一种可诱导的CO敏感、氰化物不敏感的氧化酶，需要Δ4-3-酮类固醇底物的功能性。使用2α-和2β-氘标记底物表明，在2β羟基化过程中，C-2处的氢损失是同位素依赖的，且不具有立体特异性。这被解释为底物的Δ2,4-二烯醇酶结合中间体形式。关键词：Gnomoniafructicola、羟基化、类固醇、睾酮。
• Formation of 5α steroids by biotranformation involving the 5α-reductase activity of Penicillium decumbens
  作者：Herbert L. Holland、Sophia Dore、Xu Weili、Frances M. Brown

  DOI：10.1016/0039-128x(94)90020-5

  日期：1994.11

  The biotransformation of a series of Delta(4)-3-ketosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the 5 alpha-dihydrosteroid was observed for several substrates of the androstene and pregnene series: the reaction is tolerant of non-polar subdituents (Cl and CH3) at C-4 of the substrate, but does not occur in the presence of a 4-hydroxyl group, or with additional unsaturation at the Delta(1) or Delta(6) positions. A-nor-, B-nor-, 3-deoxy-, and 3,5-cycloandrostanes are not reduced, but 6-methylenetestosterone is converted to a 6-methylene-5 alpha-dihydro derivative. Several biotransformations are reported which involve oxidoreductase activity at C-3 and/or C-17, either concomitant or independent of Delta(4) reduction: the substrate specificity of the oxidoreductase processes has been examined and defined by the use of 3 alpha-hydroxy, 3 beta-hydroxy, 3-keto, and 17 beta-hydroxy-17-keto substituted steroids. In this way, the existence in P. decumbens of 3 beta-hydroxy-3-keto and 17 beta-hydroxy-17-keto oxidoreductases has been demonstrated.
• HOLLAND, HERBERT L.;BROWN, FRANCES M.;CHENCHAIAHI, P. CHINNA;CHERNISHENKO+, CAN. J. CHEM., 67,(1989) N, C. 268-274
  作者：HOLLAND, HERBERT L.、BROWN, FRANCES M.、CHENCHAIAHI, P. CHINNA、CHERNISHENKO+

  DOI：——

  日期：——