5β-androstan-17-one | 1912-61-4

• 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: 5β-androstan-17-one
• 英文别名: 5β-Androstan-17-on；5β-Androstanon-(17)；5beta-Androstan-17-one；(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 1912-61-4
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: YJDYCULVYZDESB-USOAJAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5β-androstan-17-one 在 perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 作用下， 以 一氟三氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到(5R,8R,9S,10R,13S,14S)-5-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Direct Oxyfunctionalization at Unactivated Sites. Synthesis of 5.beta.-Hydroxysteroids by Perfluorodialkyloxaziridines

  摘要：

  By treatment with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 1a, 5 beta-steroids 2a-i (belonging to different classes, such as androstanes, cholestanes, pregnanes, and cholanic acids) have been hydroxylated in good yields and with complete site selectivity and stereoselectivity to corresponding 5 beta-hydroxy derivatives 3a-i independently from the presence of halide, ketone, carboxylic acid, and ester moieties on C-3, C-11, C-12, C-17, C-20, C-21, and C-24.

  DOI：

  10.1021/jo00098a001
• 作为产物：
  描述：

  10.13-dimethyl-17β-((R)-3-hydroxy-1-methyl-3.3-diphenyl-propyl)-5β-gonane 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 5β-androstan-17-one
  参考文献：
  名称：

  Wieland; Schlichting; Jacobi, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1926, vol. 161, p. 80,102

  摘要：

  DOI：

文献信息

• Replacement of a carbonyl group of cyclic ketones by an oxygen atom: A four-step transformation of cyclic ketones into cyclic ethers
  作者：Hiroshi Suginome、Shinji Yamada

  DOI：10.1016/0040-4039(84)80049-0

  日期：——

  We describe a new and versatile method for transforming cyclic ketones into cyclic ethers with the same ring size in which the chirality adjacent to the carbonyl group of the ketones is retained.

  我们描述了一种新的通用方法，用于将环状酮转化为具有相同环大小的环状醚，其中保留了与酮的羰基相邻的手性。
• Microbiological hydroxylation of steroids. Part IV. The pattern of dihydroxylation of mono-oxygenated 5α-androstanes with cultures of the fungus Calonectria decora
  作者：A. M. Bell、P. C. Cherry、I. M. Clark、W. A. Denny、Ewart R. H. Jones、G. D. Meakins、P. D. Woodgate

  DOI：10.1039/p19720002081

  日期：——

  concerned with the relation between the pattern of the dihydroxylation by Calonectria decora of mono-oxygenated 5α-androstane derivatives (mainly ketones), and the position of the oxygen function in the substrate. Terminal ring ketones (3, 4, 16, and 17) are converted, in useful yields, into one or two dihydroxy-ketones. (Ring B and C ketones are much less satisfactory as substrates.) The structures of most

  该工作涉及单加氧的5α-雄烷衍生物（主要是酮）的Calonectria decora的二羟基化的图案与底物中的氧官能团的位置之间的关系。将末端环酮（3、4、16和17）以有用的产率转化为一个或两个二羟基酮。（环丁酮和丙环酮作为底物要令人满意的多。）大多数产品的结构是通过光谱研究得出的。必要时通过化学相关性对这种方法进行补充
• Amphiphilic compounds with neuroprotective properties
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, v.v.i.

  公开号：US10017535B2

  公开（公告）日：2018-07-10

  Amphiphilic compounds with tetradecahydrophenanthrene skeleton and their enantiomers, exhibiting neuroprotective effects, their use in methods of treatment of neuropsychiatric disorders associated with an imbalance in glutamatergic neurotransmitter system, such as ischemic damage of CNS, neurodegenerative changes and disorders of CNS, affective disorders, depression, post-traumatic stress disorder and diseases related to stress, anxiety, schizophrenia and psychotic disorders, pain, addiction, multiple sclerosis, epilepsy, glioma, and a pharmaceutical composition containing compound.

  具有十四氢菲骨架的两性化合物及其对映体，具有神经保护作用，可用于治疗与谷氨酸能神经递质系统失衡有关的神经精神疾病，如中枢神经系统缺血性损伤、神经退行性变化和中枢神经系统紊乱、情感障碍、抑郁症、创伤后应激障碍和与应激有关的疾病、焦虑症、精神分裂症和精神病、疼痛、成瘾、多发性硬化症、癫痫、胶质瘤，以及含有化合物的药物组合物。
• Use of androstane derivatives for enhancing physical performance
  申请人：Marchewitz Eric

  公开号：US20060234993A1

  公开（公告）日：2006-10-19

  A method of decreasing body weight, reducing adipose tissue and reducing appetite in humans comprises administering a 5-Beta androstane derivative or a physiologically acceptable salt, ester or ether thereof of the general formula: wherein R3 is one of α-OH , β-OH, a mixture of α-OH and , β-OH, and O; and R7 is one of α-OH, β-OH and O.

  一种降低人体体重、减少脂肪组织和降低食欲的方法包括施用通式为 5-β-雄甾烷衍生物或其生理上可接受的盐、酯或醚： 其中R3是α-OH、β-OH、α-OH和、β-OH的混合物和O中的一种；R7是α-OH、β-OH和O中的一种。
• Nonenzymic biogenetic-like olefinic cyclizations. Cyclization of 4-(trans-3,7-octadienyl)-3-methyl-2-cyclohexen-1-ol and 4-(trans, trans-7-methyl-3,7,11-dodecatrienyl)-3-methyl-2-cyclohexen-1-ol
  作者：Kenn E. Harding、Eric J. Leopold、Anne M. Hudrlik、William S. Johnson

  DOI：10.1021/ja00815a037

  日期：1974.4