(8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1Hcyclopenta[a]phenanthrene-3,17(2H,4H)-dione | 1150096-91-5

• 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: (8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1Hcyclopenta[a]phenanthrene-3,17(2H,4H)-dione
• 英文别名: (8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthrene-3,17(2H,4H)-dione；(8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 1150096-91-5
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: XSOQSAAQKIIERG-KZQROQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1Hcyclopenta[a]phenanthrene-3,17(2H,4H)-dione 在 silver trifluoromethanesulfonate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以60%的产率得到6β-fluoro-4-androstene-3,17-dione
  参考文献：
  名称：

  Silver-Catalyzed Vinylogous Fluorination of Vinyl Diazoacetates

  摘要：

  A silver-catalyzed vinylogous fluorination of vinyl diazoacetates to generate gamma-fluoro-alpha,beta-unsaturated carbonyls is presented. Application of this method to the fluorination of farnesol and steroid derivatives was achieved.

  DOI：

  10.1021/ol403017e
• 作为产物：
  描述：

  去氢表雄酮 在 3-[(3-羧基苯基)磺酰基]-1,2-三氮杂二烯-2-鎓-1-I去 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1Hcyclopenta[a]phenanthrene-3,17(2H,4H)-dione
  参考文献：
  名称：

  Silver-Catalyzed Vinylogous Fluorination of Vinyl Diazoacetates

  摘要：

  A silver-catalyzed vinylogous fluorination of vinyl diazoacetates to generate gamma-fluoro-alpha,beta-unsaturated carbonyls is presented. Application of this method to the fluorination of farnesol and steroid derivatives was achieved.

  DOI：

  10.1021/ol403017e

文献信息

• Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton
  作者：Daniel Morton、Allison R. Dick、Debashis Ghosh、Huw M. L. Davies

  DOI：10.1039/c2cc31973j

  日期：——

  The preparation and reactivity of steroidal vinyldiazo compounds is reported, providing a convenient, substituent tolerant, chemo- and stereoselective entry into 4- and 6-substituted androgen analogues from a common precursor. Under dirhodium catalysis, O–H insertion occurs at the carbenoid site, leading to 4-substituted steroids, but under silver catalysis, O–H insertion occurs at the vinylogous position, leading to 6-substituted steroids.

  本文报道了甾体乙烯基重氮化合物的制备和反应活性，提供了一种便捷、对取代基容忍、化学选择性和立体选择性的方法，从共同前体合成4-和6-取代的雄激素类似物。在双铑催化下，O–H插入发生在卡宾位点，生成4-取代的甾体，而在银催化下，O–H插入发生在乙烯位点，生成6-取代的甾体。
• [EN] SUBSTITUTED ANDROST-4-ENE DIONES<br/>[FR] ANDROST-4-ÈNE DIONES SUBSTITUÉES
  申请人：UNIV EMORY

  公开号：WO2011127232A3

  公开（公告）日：2012-02-09
• SUBSTITUTED ANDROST-4-ENE DIONES
  申请人：Davies Huw

  公开号：US20130157988A1

  公开（公告）日：2013-06-20

  The disclosure relates to novel C4 and C6 substituted androst-4-ene diones as well as andros-1,4-diene diones and derivatives thereof, their process of preparation, pharmaceutical compounds containing them, and the use of said compounds for the treatment of hormone-related disorders in mammals. This includes hormone-dependent cancers, particularly those caused by elevated levels of estrogen and its intermediates. These compounds can also be used in the treatment of other hormone-related disorders, including benign prostatic hyperplasia, cardiovascular disease, and neurodegenerative disorders.
• US8969327B2
  申请人：——

  公开号：US8969327B2

  公开（公告）日：2015-03-03
• Silver-Catalyzed Vinylogous Fluorination of Vinyl Diazoacetates
  作者：Changming Qin、Huw M. L. Davies

  DOI：10.1021/ol403017e

  日期：2013.12.20

  A silver-catalyzed vinylogous fluorination of vinyl diazoacetates to generate gamma-fluoro-alpha,beta-unsaturated carbonyls is presented. Application of this method to the fluorination of farnesol and steroid derivatives was achieved.