B-norandrost-4-en-17β-ol-3-one | 14099-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: B-norandrost-4-en-17β-ol-3-one
• 英文别名: B-nortestosterone；17β-hydroxy-B-nor-androst-4-en-3-one；17β-Hydroxy-B-nor-androst-4-en-3-on；17β-Hydroxy-B-nor-androsten-(4)-on-(3)；17β-Hydroxy-B-norandrost-4-en-3-on；B-nor-Androst-4-en-17β-ol-3-on；(3s,3As,5as,5br,10ar,10bs)-3-hydroxy-3a,5b-dimethyl-2,3,3a,4,5,5a,5b,6,7,10,10a,10b-dodecahydrocyclopenta[a]fluoren-8(1h)-one；(3S,3aS,5aS,5bR,10aR,10bS)-3-hydroxy-3a,5b-dimethyl-2,3,4,5,5a,6,7,10,10a,10b-decahydro-1H-cyclopenta[a]fluoren-8-one
• CAS: 14099-19-5
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: XZRSOWHXIVVWJN-QQCJEOGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  B-norandrost-4-en-17β-ol-3-one 生成 B-norandrost-4-ene-3,17-dione
  参考文献：
  名称：

  HOLLAND, HERBERT L.;BROWN, FRANCES M.;CHENCHAIAHI, P. CHINNA;CHERNISHENKO+, CAN. J. CHEM., 67,(1989) N, C. 268-274

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-acetoxy-B-norandrost-5-en-17-one 在 氢氧化钾 、 sodium tetrahydroborate 、 aluminum isopropoxide 作用下， 以 甲醇 、 环己酮 、 甲苯 为溶剂， 生成 B-norandrost-4-en-17β-ol-3-one
  参考文献：
  名称：

  Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 12 - 19

  摘要：

  DOI：

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。
• Microbial hydroxylation of steroids. 7. Hydroxylation of <i>B</i>-nortestosterone and related compounds by <i>Rhizopus arrhizus</i> ATCC 11145, and ¹³C nuclear magnetic resonance spectra of some <i>B</i>-norsteroids
  作者：Herbert L. Holland

  DOI：10.1139/v81-244

  日期：1981.6.1

  been described. The products are consistent with a mechanism of oxidation at C-6 in which the stereochemistry of substitution at C-6 is controlled by stereoelectronic interactions in the substrate, and is not dictated by enzymic constraint during the reaction. The carbon-13 nuclear magnetic resonance spectra of several B-nor-Δ4 and Δ5 steroids have been presented.

  已经描述了 B-norandrost-4-ene-3-ones 和 B-nor-3β-hydroxyandrost-5-enes 与根霉 ATCC 11145 的孵化。产物与 C-6 处的氧化机制一致，其中 C-6 处取代的立体化学由底物中的立体电子相互作用控制，而不是由反应过程中的酶约束决定。已经给出了几种 B-nor-Δ4 和 Δ5 类固醇的碳 13 核磁共振谱。
• Rull; Ourisson, Bulletin de la Societe Chimique de France, 1958, p. 1573,1578
  作者：Rull、Ourisson

  DOI：——

  日期：——
• Joska et al., Chemistry and industry, 1958, p. 1665
  作者：Joska et al.

  DOI：——

  日期：——
• Joska,J. et al., Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 1086 - 1090
  作者：Joska,J. et al.

  DOI：——

  日期：——