3β-acetoxyandrosta-5,14-dien-17-one | 1239-33-4

• 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: 3β-acetoxyandrosta-5,14-dien-17-one
• 英文别名: 3β-acetoxy-androsta-5,14-dien-17-one；3β-Acetoxy-androsta-5,14-dien-17-on；(3β)-3-(acetyloxy)androsta-5,14-dien-17-one；5,14-Androstadien-3β-ol-17-on-acetat；Andre；[(3S,8R,9S,10R,13S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1239-33-4
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: LUTSRLYCMSCGCS-BWOMAWGNSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  450.5±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxyandrosta-5,14-dien-17-one 在 palladium on activated charcoal 、 potassium carbonate 、 溶剂黄146 作用下， 生成 3β-hydroxy-(5α,14β)-androstan-17-one
  参考文献：
  名称：

  Direct Introduction of Oxygen into the Steroid Nucleus. I. Studies on the Chromic Anhydride Oxidation of Dehydroisoandrosterone Acetate Dibromide¹

  摘要：

  DOI：

  10.1021/ja01141a084
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 chromium(VI) oxide 、 potassium hydrogensulfate 作用下， 生成 3β-acetoxyandrosta-5,14-dien-17-one
  参考文献：
  名称：

  Direct Introduction of Oxygen into the Steroid Nucleus. I. Studies on the Chromic Anhydride Oxidation of Dehydroisoandrosterone Acetate Dibromide¹

  摘要：

  DOI：

  10.1021/ja01141a084

文献信息

• 14-β, 17-α-hydroxymethylandrostane derivatives as androgens
  申请人：Loozen Hubert Jan Jozef

  公开号：US06881728B1

  公开（公告）日：2005-04-19

  Androgenic steroids having a (14β,17α-)-17-(hydroxymetheyl) configuration, useful for the preparation of male contraceptives and pharmaceutical formulations for the treatment of androgen insufficiency.

  雄激素类固醇具有（14β，17α-）-17-（羟甲基）配置，可用于制备男性避孕药和用于治疗雄激素不足的制药配方。
• 14 Beta, 16, 17-methylene steroids as novel androgens
  申请人：——

  公开号：US20040030165A1

  公开（公告）日：2004-02-12

  Disclosed are androgenic steroids of the (14&bgr;,17&agr;)-17-(hydroxymethyl) type. The invention relates to an improvement hereof, which is based on the presence of a &x3B2;-oriented, annellated cyclopropyl group which includes carbon atoms 16 and 17 of the steroid skeleton, i.e. a 16,17&bgr;-methylene moiety. These steroids show an unexpectedly high androgenic potency.

  本发明公开了(14&bgr;,17&agr;)-17-(羟甲基)型雄激素类固醇。本发明涉及对这种类固醇的改进，改进的基础是存在一个&x3B2;取向的环丙基，环丙基包括类固醇骨架的碳原子 16 和 17，即一个 16,17&bgr;-亚甲基。这些类固醇具有意想不到的高雄激素效力。
• Valcavi; Martelli; Sironi, Farmaco, Edizione Scientifica, 1975, vol. 30, # 6, p. 464 - 478
  作者：Valcavi、Martelli、Sironi、Tedeschi

  DOI：——

  日期：——
• 14.BETA.,17-ALPHA-HYDROXYMETHYLANDROSTANE DERIVATIVES AS ANDROGENS
  申请人：Akzo Nobel N.V.

  公开号：EP1163259B1

  公开（公告）日：2002-11-20
• Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data
  作者：A. V. Baranovskii、D. A. Bolibrukh、V. V. Gromak

  DOI：10.1134/s1070363211090234

  日期：2011.9

  On the basis of dehydroepiandrosterone through the Delta(14)- and Delta(15)-androst-17-ones a series of androsta-14,16-dienyl acetates was obtained, the key compounds in the synthesis of 14-substituted steroids. By the methods of two-dimensional NMR spectroscopy the structure of compounds was proved and a full assignment of signals in the H-1 and C-13 NMR spectra was performed. With the use of tandem mass spectrometry the main directions of fragmentation of protonated molecules of the synthesized ketones and dienyl acetates were studied. DOI: 10.1134/S1070363211090234