6-aza-4-pregnene-3,20-dione | 1417534-91-8

• 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: 6-aza-4-pregnene-3,20-dione
• 英文别名: 6-azaprogesterone；(1S,3aS,3bS,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9b,10,11-dodecahydrocyclopenta[i]phenanthridin-7-one
• CAS: 1417534-91-8
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: HJPIUORYXATJGR-GKQOSVPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3β-tert-butyldimethylsilyloxy-7-azido-19-formyloxy-6-nor-5,7-secopregnane-5,20-dione 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 过氧化双月桂酰 、 二苯基硅烷 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 14.5h， 生成 6-aza-4-pregnene-3,20-dione
  参考文献：
  名称：

  Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids

  摘要：

  19-Hydroxy-6-azapregnanes were obtained from pregnenolone via a 7-azido-5-oxo-6-nor-5,7-secopregnane intermediate. The 6-azapregnane core was built in good yield in a straightforward way from the secosteroid, by means of a Staudinger (aza-Wittig) reaction. Finally the 19-hydroxy-6-azapregnane was transformed into 19-hydroxy-6-azaprogesterone (that cyclized spontaneously to the 19 -> 3 hemiketal) and 6-azaprogesterone. The 6-azapregnanes lacked agonistic/antagonistic activity on the progesterone receptor. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.10.012

文献信息

• Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
  作者：Mario D. Martínez、Valeria C. Edelsztein、Fernando J. Durán、Pablo H. Di Chenna、Gerardo Burton

  DOI：10.1016/j.steroids.2012.10.012

  日期：2013.1

  19-Hydroxy-6-azapregnanes were obtained from pregnenolone via a 7-azido-5-oxo-6-nor-5,7-secopregnane intermediate. The 6-azapregnane core was built in good yield in a straightforward way from the secosteroid, by means of a Staudinger (aza-Wittig) reaction. Finally the 19-hydroxy-6-azapregnane was transformed into 19-hydroxy-6-azaprogesterone (that cyclized spontaneously to the 19 -> 3 hemiketal) and 6-azaprogesterone. The 6-azapregnanes lacked agonistic/antagonistic activity on the progesterone receptor. (C) 2012 Elsevier Inc. All rights reserved.