3β-acetoxy-17-azaandrost-5-en-16-one | 14417-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3β-acetoxy-17-azaandrost-5-en-16-one
• 英文别名: [(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-2-oxo-1,3,3a,3b,4,6,7,8,9,9b,10,11-dodecahydronaphtho[2,1-e]indol-7-yl] acetate
• CAS: 14417-98-2
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: OHSDSMZCSFAOPT-KCMORZRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-17-azaandrost-5-en-16-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以96%的产率得到3β-hydroxy-17-azaandrost-5-en-16-one
  参考文献：
  名称：

  Back, Thomas G.; Lai, Enoch K.Y.; Morzycki, Jacek W., Heterocycles, 1991, vol. 32, # 3, p. 481 - 488

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-acetoxy-16,17-seco-androst-5-ene-16,17-dioic acid-16-nitrile 在 吡啶 、 氢氧化钾 、 二苯基膦叠氮化物 、 水 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 35.5h， 生成 3β-acetoxy-17-azaandrost-5-en-16-one
  参考文献：
  名称：

  Back, Thomas G.; Lai, Enoch K.Y.; Morzycki, Jacek W., Heterocycles, 1991, vol. 32, # 3, p. 481 - 488

  摘要：

  DOI：

文献信息

• Studies on the construction of the 2-isooctyl side chain in 17-azasteroids
  作者：J. W. Morzycki、Z. Łotowski

  DOI：10.1007/bf00811765

  日期：1995.1

  The transformations of (20R)- and (20S)-3 beta-hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitriles towards the 17-aza analogue of cholesterol are described. Attempts of a direct addition of a four carbon atom fragment to nitriles were unsuccessful. Alternately, nitriles were transformed via carboxylic acids, methyl esters and primary alcohols into iodides. The coupling reaction of(20S)-iodide with (i-Bu)(2)CuLi afforded the desired product in low yield but failed in the case of the 20R epimer.
• Synthesis of 4,17-diazasteroid inhibitors of human 5α-reductase
  作者：Jacek W. Morzycki、Zenon z.xl;Lotowski、Agnieszka Z. Wilczewska、J. Darren Stuart

  DOI：10.1016/0968-0896(96)00109-5

  日期：1996.8

  The synthesis of the 17-aza isomer of finasteride is described. With the side chain amide group of the compound existing in the Z configuration the structure is similar to one of the two favored conformations of finasteride. A series of 4,17-diazasteroids was assayed against the isoenzymes of human 5 alpha-reductase. Copyright (C) 1996 Elsevier Science Ltd
• Structure of 3β-hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitrile and its 20S epimer
  作者：Jacek W. Morzycki、Zenon Łotowski、Leszek Siergiejczyk、Janusz Lipkowski、Anna Tabaszewska、Jacek Wójcik

  DOI：10.1016/0039-128x(94)00037-d

  日期：1995.2

  The structures of the title compounds have been investigated in solid state by X-ray and in solution by NMR methods. The configurations at C20 and the preferred conformations of both epimers were established. A full assignment of signals in H-1 and C-13 NMR spectra was done.
• N-Alkylation of 17-azasteroids
  作者：J MORZYCKI、Z LOTOWSKI

  DOI：10.1016/0039-128x(94)90042-6

  日期：1994.1

  N-Alkylation of 17-azasteroid lactams (16-oxo-17-azaandrost-5-en-3 beta-ol acetate 3 and its D-homo analog 4) was studied. It has been found that both lactams are readily alkylated with iodomethane or iodoethane. In contrast to this there was no reaction with 2-iodo-6-methylheptane due to the steric hindrance. 1,4-Addition of lactam to the conjugated systems was also studied. The addition to acrylonitrile proved to be easy compared to crotononitrile. However the efficient addition to the latter compound was also attained by using potassium t-butoxide as a base in t-butanol.
• BACK, THOMAS G.;LAI, ENOCH K. Y.;MORZYCKI, JACEK W., HETEROCYCLES, 32,(1991) N, C. 481-488
  作者：BACK, THOMAS G.、LAI, ENOCH K. Y.、MORZYCKI, JACEK W.

  DOI：——

  日期：——