androstan-17-one | 36378-49-1

• 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: androstan-17-one
• 英文别名: 17-oxoandrostane；(5ξ)-androstan-17-one；(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: 36378-49-1
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: YJDYCULVYZDESB-HQEMIIEJSA-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：

  1,3-丙二硫醇 、 androstan-17-one 在 四溴环己二烯-1-酮 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以87%的产率得到(8R,9S,10S,13S,14S)-10,13-dimethylspiro[1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dithiane]
  参考文献：
  名称：

  2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为羰基化合物二硫代缩醛化和氧硫代缩醛化以及转二硫代缩醛化反应的有效催化剂

  摘要：

  使用 2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为有效催化剂将羰基化合物转化为环状和无环二硫缩醛和 1,3-描述了在温和反应条件下的硫杂环戊烷。这些催化剂还用于在硫醇存在下以高产率有效地将缩醛、二缩醛、缩酮、酰基、烯胺、腙和肟转二硫缩醛。

  DOI：

  10.1080/10426500211712
• 作为产物：
  描述：

  14β-hydroxy-9(11)-androstene-3,17-dione 以 溶剂黄146 为溶剂， 以70 mg. (~70%)的产率得到androstan-17-one
  参考文献：
  名称：

  14.beta.-Hydroxyandrostanes

  摘要：

  本发明涉及14-β-羟基雄烷类化合物及其制备方法，其中14-β-羟基基团通过一种新颖的环化反应内部构建于8,14-去氢-4,6,9（11）-雄烷三烯-3,14,17-三酮中。这些14-β-羟基雄烷类化合物可用作合成强心苷及相关产品的前体。

  公开号：

  US04134920A1

文献信息

• NEW STEROIDS HAVING INCREASED WATER SOLUBILITY AND RESISTANCE AGAINST METABOLISM, AND METHODS FOR THEIR PRODUCTION
  申请人：BACKSTROM Torbjorn

  公开号：US20080119416A1

  公开（公告）日：2008-05-22

  Steroid compounds having increased resistance against metabolism and increased water solubility are disclosed, together with methods for their production. These substances are suitable for the manufacture of pharmaceuticals for the treatment of steroid related or steroid induced CNS disorders and for use in methods of prevention, alleviation or treatment of such disorders.

  揭示了具有增加代谢抵抗力和增加水溶性的类固醇化合物，以及它们的生产方法。这些物质适用于制造用于治疗与类固醇相关或类固醇诱导的中枢神经系统疾病的药物，并用于预防、缓解或治疗此类疾病的方法。
• [EN] C-HALOGEN BOND FORMATION<br/>[FR] FORMATION DE LIAISON C-HALOGÈNE
  申请人：GROVES JOHN T

  公开号：WO2013028639A1

  公开（公告）日：2013-02-28

  Methods of halogenating a carbon containing compound having an sp3 C-H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C-H fluorination of a carbon containing compound having an sp3 C-H bond are provided. The halogenated products of the methods are provided.

  提供了一种卤代含有sp3 C-H键的碳化合物的卤代方法。提供了一种包括用Cl或Br进行卤代，然后用F进行亲核取代的卤代碳化合物的氟化方法。提供了一种直接氧化C-H氟化的含有sp3 C-H键的碳化合物的方法。提供了这些方法的卤代产物。
• [EN] AMPHIPHILIC COMPOUNDS WITH NEUROPROTECTIVE PROPERTIES<br/>[FR] COMPOSÉS AMPHIPHILES DOTÉ DE PROPRIÉTÉS NEUROPROTECTRICES
  申请人：USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR V V I

  公开号：WO2016029888A1

  公开（公告）日：2016-03-03

  The present invention provides amphiphilic compounds with tetradecahydrophenanthrene skeleton and their enantiomers, exhibiting neuroprotective effects, their use as medicaments for treating 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 said compound.

  本发明提供了具有十四氢苯并骨架及其对映体的两性化合物，表现出神经保护作用，它们可用作治疗与谷氨酸能神经递质系统失衡相关的神经精神障碍的药物，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障碍、情感障碍、抑郁症、创伤后应激障碍以及与压力、焦虑、精神分裂症和精神障碍、疼痛、成瘾、多发性硬化、癫痫、胶质瘤有关的疾病，以及含有该化合物的药物组合物。
• [EN] INHIBITORS OF 17ß-HSD1, 17ß-HSD3 AND 17ß-HSD10<br/>[FR] INHIBITEURS DE 17SS-HSD1, 17SS-HSD3 ET 17SS-HSD10
  申请人：UNIV LAVAL

  公开号：WO2012129673A1

  公开（公告）日：2012-10-04

  The present application discloses 17β hydroxy steroid dehydrogenase (17β HSD) type 1, 3, 10 inhibitors and use thereof (alone and in combination) in the treatment of cancer and other afflictions. 17β HSDl inhibitors include estradiol derivatives with a nieta-carbamoylbenzyl substituent at C 16. 17β HSD3/HSD10 inhibitors include androsterone derivatives substituted at the C3 position with a sulfonamide piperazine. Also disclosed are compounds that are inhibitors of both 17β HSDl and 17β HSD3 that have a spiro-morpholine substituent at C20.

  该申请公开了17β羟基类固醇脱氢酶（17β HSD）类型1、3、10的抑制剂及其在癌症和其他疾病治疗中的使用（单独和组合使用）。17β HSD1抑制剂包括在C16处带有尼达-氨甲酰苯甲基取代基的雌二醇衍生物。17β HSD3/HSD10抑制剂包括在C3位置用磺胺基哌嗪取代的雄甾酮衍生物。还公开了既是17β HSD1又是17β HSD3抑制剂的化合物，其在C20处带有螺环吗啡基取代基。
• (17R)-Spiro-[androstane-17,1'-cyclobutan]-2'-ones, methods for their
  申请人：Schering Corporation

  公开号：US03968132A1

  公开（公告）日：1976-07-06

  (17R)-Spiro-[androstane-17,1'-cyclobutan]-2'-ones are prepared by the reaction of a 17-oxo androstane, wherein all other ketones are blocked, with a cyclopropylarylsulfide or with a cyclopropylarylsulfonium salt having a non-nucleophilic anion, in an organic solvent together with a strong base, followed by reaction in situ of the intermediate thereby formed with aqueous acid or water. Some (17R)-spiro-[androstan-17,1'-cyclobutan]-2'-ones are useful as intermediates in preparing (17R)-spiro-[3-oxo-4-androstene-17,1'-cyclobutan]-2'-ones which are aldosterone antagonists. Additionally, (17R)-spiro-[androstane-17,1'-cyclobutan]-2'-ones are useful as intermediates in preparing known 17.alpha.-pregnane-21,17.beta.-carbolactones, valuable aldosterone blocking agents.

  (17R)-spiro-[雄甾烷-17,1'-环丁基]-2'-酮是通过将17-酮雄甾烷（其中所有其他酮被阻断）与环丙基芳基硫醚或具有非亲核阴离子的环丙基芳基硫鎓盐在有机溶剂中与强碱反应，随后与水溶酸或水原位反应而制备的。一些(17R)-spiro-[雄甾烷-17,1'-环丁基]-2'-酮可用作制备(17R)-spiro-[3-氧代-4-雄烷烯-17,1'-环丁基]-2'-酮的中间体，后者是醛固酮拮抗剂。此外，(17R)-spiro-[雄甾烷-17,1'-环丁基]-2'-酮可用作制备已知的17α-孕烷-21,17β-羧内酯，这是有价值的醛固酮阻滞剂的中间体。