13β-H-18-norandrost-4-ene-3,17-dione | 93998-22-2

• 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: 13β-H-18-norandrost-4-ene-3,17-dione
• 英文别名: 4-androstene-3,17-dione；Gon-4-ene-3,17-dione, 10-methyl-；(8S,9S,10R,13S,14S)-10-methyl-1,2,6,7,8,9,11,12,13,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 93998-22-2
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: ZAIYWORKAVGTME-DNCCFGNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  18-hydroxypregn-4-ene-3,20-dione (18<*>20)hemiketal 在 吡啶 、 重铬酸吡啶 、 双氧水 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 对甲苯磺酸 、 三甲胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 53.67h， 生成 13β-H-18-norandrost-4-ene-3,17-dione
  参考文献：
  名称：

  An improved synthesis of 18-norandrost-4-ene-3,17-dione

  摘要：

  We describe the synthesis of 13beta- and 13alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18 --> 20) hemiketal, via the 18-acetoxy-17beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a ''one-pot'' procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.

  DOI：

  10.1016/0039-128x(93)90051-n

文献信息

• Investigation of the Moffatt−Swern Oxidation in a Continuous Flow Microreactor System
  作者：Jacobus J. M. van der Linden、Peter W. Hilberink、Claudia M. P. Kronenburg、Gerardus J. Kemperman

  DOI：10.1021/op700228e

  日期：2008.9.19

  The Moffatt-Swern oxidation of different alcohols is performed in a continuous flow microreactor system. The microreactor process offers significant advantages over the batch process. First, because of the small reactor volume, accumulation of the labile trifluoroacetoxydimethylsulfonium salt (3) and alkoxydimethyl-sulfonium salt (5) is minimized. Second, because of the short residence times, which can be applied in the microreactor, the exothermic Pummerer rearrangement of the unstable intermediate 3 is limited. Because of this, the process can be operated at remarkably high temperatures in comparison with a batch reaction, viz. 0-20 degrees C instead of -70 degrees C. In the present study, a continuous flow microreactor system was optimized using reactors of different volumes allowing modulation of the residence times of labile intermediates. The efficiency of mixing was studied using different mixing devices. It has been shown that the continuous How microreactor is an ideal tool for rapid optimization of reaction parameters. Furthermore, the scaleability and reliability of the microreactor was tested by running the system for several hours. For testosterone, the system was in process for 1.5 h without any problems, resulting in an 4-androstene-3,17-dione production rate of 64 g center dot h(-1).
• An improved synthesis of 18-norandrost-4-ene-3,17-dione
  作者：Elisabeth Davioud、Philippe Schambel、Antoinette Viger、Andrée Marquet

  DOI：10.1016/0039-128x(93)90051-n

  日期：1993.3

  We describe the synthesis of 13beta- and 13alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18 --> 20) hemiketal, via the 18-acetoxy-17beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a ''one-pot'' procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.