androst-5-ene-17β-ol | 6197-89-3

• 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: androst-5-ene-17β-ol
• 英文别名: 17β-hydroxy-10.13-dimethyl-gonene-(5)；17β-Hydroxy-10.13-dimethyl-gonen-(5)；(10R)-17c-Hydroxy-10r.13c-dimethyl-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 6197-89-3
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: ADWFPYROOHCVON-DYKIIFRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  androst-5-ene-17β-ol 在 chromium(VI) oxide 、 氯仿 、 溶剂黄146 作用下， 生成 睾酮
  参考文献：
  名称：

  Sterols. LXXXVI. Desoxotestosterone and its Conversion to Testosterone

  摘要：

  DOI：

  10.1021/ja01858a065
• 作为产物：
  描述：

  去氢表雄酮 生成 androst-5-ene-17β-ol
  参考文献：
  名称：

  Bascoul,J. et al., Bulletin de la Societe Chimique de France, 1972, p. 2744 - 2748

  摘要：

  DOI：

文献信息

• Novel derivatives of androstane and androstene with ascorbic acid and use thereof in treating or preventing various conditions, diseases, and disorders
  申请人：FORBES MEDI-TECH INC.

  公开号：US20030232797A1

  公开（公告）日：2003-12-18

  The present invention provides novel derivatives comprising compounds in the androstane and androstene series, coupled with ascorbic acid, including salts thereof, and represented by one or more of the general formulae: 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 may individually be chosen from hydrogen, OH, carbonyl, and an ascorbyl moiety; and R 7 may be hydrogen or any halogen.

  本发明提供了包括雄烷和雄烯系列化合物与抗坏血酸结合的新颖衍生物，包括其盐，并由下列一个或多个通式表示： 其中R1、R2、R3、R4、R5、R6可以分别选择为氢、OH、羰基和抗坏血酸基团；R7可以是氢或任何卤素。
• Reductive cleavage of N,N,N′,N′-tetramethylphosphorodiamidates with lithium naphthalenide. A convenient procedure for deoxygenation of alcohols
  作者：Hsing-Jang Liu、Xiao Shang

  DOI：10.1016/s0040-4039(97)10602-5

  日期：1998.1

  A simple, effective alternative procedure has been developed for the reductive cleavage of the N,N,N′,N′-tetramethylphosphorodiamidate group, using lithium naphthalenide as the reagent.

  已经开发了一种简单有效的替代方法，使用萘二甲酸锂作为试剂对N，N，N'，N'-四甲基磷酸二氨基酯基进行还原裂解。
• Compositions comprising one or more policosanols and/or policosanoic acids combined with sterol and/or steroid based ascorbic acid derivatives, and uses thereof
  申请人：Kutney P. James

  公开号：US20050234025A1

  公开（公告）日：2005-10-20

  A composition comprises one or more long chain alcohols (policosanols) and/or their respective acids (policosanoic acids) and one or more ascorbic acid derivatives, including all biologically acceptable salts or solvates or prodrugs of at least one such derivative or of the salts or of the solvates thereof and is used for the treatment and prevention of a variety of conditions and disorders.

  一种组合物包括一种或多种长链醇（聚醇）和/或它们各自的酸（聚酸）以及一种或多种抗坏血酸衍生物，包括至少一种这种衍生物或其盐或溶剂或前药的生物学上可接受的所有盐或溶剂，用于治疗和预防各种疾病和紊乱。
• Potential organ or tumor-imaging agents. 16. Fluorinated androstanes and the prostate
  作者：Andre Castonguay、Raymond E. Counsell、R. W. Scot Skinner、Rodney V. Pozderac

  DOI：10.1021/jm00202a015

  日期：1978.4

  A series of substituted 5alpha-androstan-17beta-ols was synthesized and evaluated for their potential use in the development of a prostate imaging agent. The ability of the synthesized compounds to compete with [3H]-5alpha-dihydrotestosterone for rat prostate androgen receptor protein served as the screening assay. For 3-substituted derivatives, the order of binding to the androgen receptor protein

  合成了一系列取代的5α-雄激素-17β-醇，并评估了它们在前列腺成像剂开发中的潜在用途。合成的化合物与[3H]-5α-二氢睾酮竞争大鼠前列腺雄激素受体蛋白的能力用作筛选测定。对于3取代的衍生物，与雄激素受体蛋白的结合顺序为= O大于-OH大于H近似等于F。3beta-Fluoro-5alpha-androstan-17beta-ol被发现具有大约5％的去势大鼠丙酸睾丸激素的雄激素活性。3β-氟衍生物的低生物活性，再加上与引入氟18相关的合成障碍，导致我们寻找更合适的卤素类固醇作为潜在的放射诊断手段。
• Imprinted Polymers as Protecting Groups for Regioselective Modification of Polyfunctional Substrates
  作者：Cameron Alexander、Craig R. Smith、Michael J. Whitcombe、Evgeny N. Vulfson

  DOI：10.1021/ja982238h

  日期：1999.7.1

  selective solvent extractions, and chemical modification experiments. The feasibility of using imprinted polymers as reusable protecting groups was established by the regioselective acylation of trihydroxysteroids bound to polymers imprinted with structurally related diols. In polymers prepared with tert-butyl ester templates “matched” to the substrate, regioselectivities as high as 23.1:1 (24-acetate:3-acetate)

  印迹聚合物是使用衍生自硼苯酞的功能单体和许多带有空间分离羟基的类固醇模板制备的。结合相互作用的协同性质在印有雄激素-5-烯-3β,17β-二醇及其结构类似物的聚合物中得到证实。使用红外光谱、选择性溶剂萃取和化学改性实验来探测结合的化学计量和动力学。使用印迹聚合物作为可重复使用的保护基团的可行性是通过与印有结构相关二醇的聚合物结合的三羟基类固醇的区域选择性酰化来确定的。在用与底物“匹配”的叔丁酯模板制备的聚合物中，区域选择性高达 23.1:1（24-乙酸酯：观察到单酯产物（回收材料的 65%）中的 3-乙酸酯）。在“不匹配”的情况下，比例下降到 5.4:1；然而，在功能相同的控制聚合物中，印有乙二醇，区域...