17β-Acetoxy-A-nor-5α-androstan-2-on | 1162-88-5

• 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-Acetoxy-A-nor-5α-androstan-2-on
• 英文别名: 2-Oxo-17β-acetoxy-A-nor-5α-androstan；[(3aS,3bS,5aS,6S,8aS,8bR,10aS)-3a,5a-dimethyl-2-oxo-3,3b,4,5,6,7,8,8a,8b,9,10,10a-dodecahydro-1H-indeno[5,4-e]inden-6-yl] acetate
• CAS: 1162-88-5
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: KZDDFUXUOIKOLA-VHUDCFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  17β-Acetoxy-A-nor-5α-androstan-2-on 在 palladium on activated charcoal 2,3,5-三甲基吡啶 、 氢溴酸 、 氢气 、 溴 作用下， 以 溶剂黄146 、 xylene 为溶剂， 生成 17β-Acetoxy-2-oxo-A-nor-5β-androstan
  参考文献：
  名称：

  Hanna,R. et al., Bulletin de la Societe Chimique de France, 1961, p. 1209 - 1212

  摘要：

  DOI：
• 作为产物：
  描述：

  [(5S,8R,9S,10S,13S,14S,17S)-10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基]环己烷羧酸酯 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 17β-Acetoxy-A-nor-5α-androstan-2-on
  参考文献：
  名称：

  Rull; Ourisson, Bulletin de la Societe Chimique de France, 1958, p. 1573,1578

  摘要：

  DOI：

文献信息

• Steroidal nitrone inhibitors of 5α-reductase
  作者：Andrea J Robinson、Indawati DeLucca、Spencer Drummond、George A Boswell

  DOI：10.1016/s0040-4039(03)00741-x

  日期：2003.6

  This paper describes the rational design and synthesis of novel inhibitors of human steroid 5α-reductase. Steroidal nitrones were synthesised via an eight-step sequence from epiandrosterone and were tested for activity against type I and II 5α-reductase isozymes. Judicious placement of the nitrone into the steroid A-ring provided an effective and stable transition-state mimic of the postulated enolate

  本文描述了新型人类固醇5α-还原酶抑制剂的合理设计和合成。从表雄甾酮通过八步序列合成甾族硝酮，并测试其对I型和II型5α-还原酶同工酶的活性。将硝酮明智地置于类固醇A环中，可有效且稳定地模拟与睾丸酮转化为二氢睾丸激素有关的假定的烯醇酸酯中间体。
• Syntheses of 1α, 2α-and 1β, 2β-Epithio-A-nor-5α-androstan-17β-ol and Related Compounds.
  作者：Keiji Yoshida、Fumihiko Watanabe

  DOI：10.1248/cpb.15.1966

  日期：——

  17β-Hydroxy-A-nor-5α-androstan-1α, 2α-episulfide (XXIIIa) and -1β, 2β-episulfide (XIa) were prepared from 17β-acetoxy-A-nor-5α-androstan-2-one (Ib) via the corresponding epoxides (XXa) and (IXa) as intermediates.

  以 17β-acetoxy-A-nor-5α-androstan-2-one (Ib) 为中间体，通过相应的环氧化物 (XXa) 和 (IXa)，制备出 17β-Hydroxy-A-nor-5α-androstan-1α, 2α-episulfide (XXIIIa) 和 -1β, 2β-episulfide (XIa)。
• Circular dichroism and optical rotatory dispersion of some hexahydroindanone derivatives; methyl- and methylene-substituted steroid ketones
  作者：M. J. Brienne、A. Heymes、J. Jacques、G. Snatzke、W. Klyne、S. R. Wallis

  DOI：10.1039/j39700000423

  日期：——

  Circular dichroism and optical rotatory dispersion curves of a number of steroid hexahydroindanones have been measured. The compounds were A-nor-5α-androstan-2-ones and 5α-androstan-16-ones carrying methyl groups in positions adjacent to carbonyl. The curves are discussed in relation to the probable conformations of the cyclopentanone ring. Some data on related αβ-unsaturated ketones are also included

  已经测量了许多类固醇六氢茚满酮的圆二色性和旋光色散曲线。这些化合物是在与羰基相邻的位置带有甲基的A -nor-5α-雄甾烷-2-酮和5α-雄甾烷-16-酮。讨论了关于环戊酮环的可能构型的曲线。还包括一些有关αβ-不饱和酮的数据。
• Oxidation of steroidal ketones—vi
  作者：E. Caspi、S.K. Malhotra、Y. Shimizu、K. Maheshwari、M.J. Gasic

  DOI：10.1016/0040-4020(66)80028-5

  日期：——

  The mechanism of selenium dioxide-hydrogen peroxide oxidation of saturated steroidal-3-ketones was investigated with the use of 2,2,4,4-D4-17β-hydroxy-5α-androstane-3-one. It was proven that formation of lactones II and III proceeds through a process analogous to Baeyer-Villiger oxidation. Formation of ring contracted acid (IV) was subject to a primary isotope effect with considerable C-D bond breakage

  饱和甾-3-酮的二氧化硒-过氧化氢的氧化的机理与使用2,2,4,4- d的考察4 -17β羟基5α -雄甾烷-3-酮。业已证明，内酯II和III的形成是通过类似于Baeyer-Villiger氧化的过程进行的。在速率测定步骤中，形成环缩合酸（Ⅳ）的过程具有主要的同位素效应，即相当大的C-D键断裂。由此推断，IV是通过酮的烯醇化而产生的。A环收缩的酸基本上保留了三个D原子，因此不包括平衡。
• Al-Footy, Khalid; Hanson, James R.; Uyanik, Cavit, Journal of Chemical Research, Miniprint, 1999, # 5, p. 1320 - 1330
  作者：Al-Footy, Khalid、Hanson, James R.、Uyanik, Cavit

  DOI：——

  日期：——