17β-hydroxy-4,4-dimethylandrostan-3-one | 54550-06-0

• 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-4,4-dimethylandrostan-3-one
• 英文别名: 17β-Hydroxy-4,4-dimethyl-5α-androstan-3-on；4,4-Dimethylandrostan-3-on-17 β-ol；4.4-Dimethyl-5α-androstan-17β-ol-on-(3)；17β-hydroxy-4,4-dimethyl-5α-androstan-3-one；Androstan-3-one, 17-hydroxy-4,4-dimethyl-, (5alpha,17beta)-；(5R,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13-tetramethyl-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 54550-06-0
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: SUGWZEKPIYGDGP-ZIKYFWMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  17β-hydroxy-4,4-dimethylandrostan-3-one 在 咪唑 、 正丁基锂 、 水 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.41h， 生成 (5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-4,4,10,13-tetramethyl-3-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthrene-2-carbonitrile
  参考文献：
  名称：

  [EN] COMPOUNDS INCLUDING AN ANTI-INFLAMMATORY PHARMACORE AND METHODS OF USE
  [FR] COMPOSÉS COMPRENANT UN PHARMACORE ANTI-INFLAMMATOIRE ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2009146218A8
• 作为产物：
  描述：

  睾酮 在 甲醇 、 palladium on activated charcoal 、 potassium tert-butylate 作用下， 生成 17β-hydroxy-4,4-dimethylandrostan-3-one
  参考文献：
  名称：

  Steroids. LXXXV.¹ Synthesis of 4-Methyl and 4,4-Dimethyl Hormone Analogs²

  摘要：

  DOI：

  10.1021/jo01357a002

文献信息

• The synthesis of (–)-sandaracopimaradiene from androstane derivatives
  作者：P. Johnston、R. C. Sheppard、C. E. Stehr、S. Turner

  DOI：10.1039/j39660001847

  日期：——

  D by reduction of the ozonide and selective oxidation of the seco-diol or triol with manganese dioxide yielded ring-D homo-lactones, which were converted by way of the β-keto-lactone into (–)-sandaracopimaradiene.

  描述了睾丸激素和3β-羟基雄烷-5-en-17-one到二萜sandaracopimaradiene的转化。通过对5，7-二烯进行酸催化的异构化，加氢以及进一步对所得的8（14）-烯烃进行异构化来制备4，4-二甲基-5α-雄烷-14-烯及其17β-羟基衍生物。通过还原臭氧化物还原D环，并用二氧化锰选择性氧化癸二醇或三醇，得到D环均内酯，其通过β-酮内酯转化为（-）-sandaracopimaradiene。
• Further Preparation of Steroidal Diosphenols. I. Synthesis of Some 4, 4-Dimethyl-2-hydroxy-3-oxo-1-ene Steroids in Androstane and Pregnane Series
  作者：HIROMU MORI、JOJI YAMADA、YOSHIO TAKAHASHI、KIKUO YASUDA、KIYOSHI TSUNEDA、KENYU SHIBATA、SHUNYO WADA、OSAMU TAKATANI

  DOI：10.1248/cpb.16.1795

  日期：——

  Some 2-hydroxy-3-oxo-4, 4-dimethyl-1-ene steroids and two 4-hydroxy-3-oxo-2, 2-dimethyl-4-ene steroids were prepared in order to obtain anti-tumor substances against sex hormone dependent cancer such as breast cancer and prostatic cancer. These diosphenols were synthesized by the autoxidation of the corresponding 3-oxo steroids in the presence of potassium tert-butoxide in tert-butanol.

  一些2-羟基-3-氧-4, 4-二甲基-1-烯类类固醇和两种4-羟基-3-氧-2, 2-二甲基-4-烯类类固醇被制备出来，以获得对依赖性性激素的癌症（如乳腺癌和前列腺癌）的抗肿瘤物质。这些二氧芬酚是在存在氢氧化钾叔丁醇的条件下，通过相应的3-氧类固醇的自氧化反应合成的。
• GB1175219
  申请人：——

  公开号：——

  公开（公告）日：——
• Ferguson, George; Macaulay, Ernest W.; Robertson, J. Monteath, Journal of the Chemical Society. Perkin transactions II, 1980, p. 1170 - 1175
  作者：Ferguson, George、Macaulay, Ernest W.、Robertson, J. Monteath、Midgley, John M.、Whalley, W. Basil、Lodge, Bruce A.

  DOI：——

  日期：——
• COMPOUNDS INCLUDING AN ANTI-INFLAMMATORY PHARMACORE AND METHODS OF USE
  申请人：Anderson Eric

  公开号：US20100048887A1

  公开（公告）日：2010-02-25

  This invention provides novel compounds comprising the following anti-inflammatory pharmacore: wherein X, R 1 and R 2 are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds, methods and intermediates useful for making the compounds, and methods of using the compounds and compositions.