17β-hydroxy-2-hydroxymethylene-5α-androstan-3-one | 4033-95-8

• 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: 17β-hydroxy-2-hydroxymethylene-5α-androstan-3-one
• 英文别名: 2-hydroxymethylene-17β-hydroxy-5α-androstan-3-one；2-hydroxymethylene-5α-androst-17β-ol-3-one；4,5α-dihydro-2-(hydroxymethylene)testosterone；2--(hydroxymethylidene)androstanolone；oxystanolone；17β-hydroxy-3-oxo-(5α)-androstane-2-carbaldehyde；4,5alpha-Dihydro-2-(hydroxymethylene)testosterone；(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 4033-95-8
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: DKCLFTBKKHWBQS-YNZDMMAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-2-hydroxymethylene-5α-androstan-3-one 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 屈他雄酮
  参考文献：
  名称：

  α-取代环酮的直接区域选择性脱氢

  摘要：

  描述了在 2,3-二氯苯并-5,6-二氰基-1,4-苯醌存在下，α-取代环酮的高度区域选择性一步脱氢。该反应通过基于磷酸的烯醇催化进行，并提供多种 α-芳基和 α-烷基取代的 α,β-不饱和酮。

  DOI：

  10.1002/anie.202307081
• 作为产物：
  描述：

  (10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基)乙酸酯 在 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 17β-hydroxy-2-hydroxymethylene-5α-androstan-3-one
  参考文献：
  名称：

  Sciaky,R.; Pallini,U., Gazzetta Chimica Italiana, 1966, vol. 96, p. 1241 - 1253

  摘要：

  DOI：

文献信息

• New steroidal heterocycles: androstano[3,2-b](pyrimido[1,2-a]benzimidazoles)
  作者：Joginder S. Bajwa、Peter J. Sykes

  DOI：10.1039/p19800001859

  日期：——

  The preparation of steroidal heterocycles containing the pyrimido[1,2-a]benzimidazole ring system fused to the 2,3-position of the steroid nucleus is described. These are prepared by the reaction of 2-aminobenzimidazole with 2-hydroxymethylene-3-oxo-steroids.

  描述了含有与类固醇核的2,3-位稠合的嘧啶并[1,2- a ]苯并咪唑环系统的类固醇杂环的制备。这些是通过2-氨基苯并咪唑与2-羟基亚甲基-3-氧代甾族化合物的反应制备的。
• A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates
  作者：Christopher C. Waller、Malcolm D. McLeod

  DOI：10.1016/j.steroids.2014.09.006

  日期：2014.12

  Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17 beta-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17 beta-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17 beta-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 mu g of testosterone (17 beta-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS). (C) 2014 Elsevier Inc. All rights reserved.
• Al-Fouti, Khaled; Hanson, James R., Journal of Chemical Research, Miniprint, 2003, # 1, p. 143 - 152
  作者：Al-Fouti, Khaled、Hanson, James R.

  DOI：——

  日期：——
• [EN] NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF<br/>[FR] STÉROÏDES NEUROACTIFS, COMPOSITIONS, ET LEURS UTILISATIONS
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2015010054A3

  公开（公告）日：2015-04-09
• de Ruggieri,P. et al., Gazzetta Chimica Italiana, 1962, vol. 92, p. 768 - 798
  作者：de Ruggieri,P. et al.

  DOI：——

  日期：——