19-hydroxy-6-(tert-butoxycarbonyl)-6-aza-4-pregnene-3,20-dione | 1417534-96-3

• 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: 19-hydroxy-6-(tert-butoxycarbonyl)-6-aza-4-pregnene-3,20-dione
• 英文别名: tert-butyl (1S,3aS,3bS,9aS,9bS,11aS)-1-acetyl-9a-(hydroxymethyl)-11a-methyl-7-oxo-2,3,3a,3b,4,8,9,9b,10,11-decahydro-1H-cyclopenta[i]phenanthridine-5-carboxylate
• CAS: 1417534-96-3
• 化学式: C₂₅H₃₇NO₅
• 分子量: 431.572
• InChiKey: UYQLPQRZPILHQI-DNWMOIJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  19-hydroxy-6-(tert-butoxycarbonyl)-6-aza-4-pregnene-3,20-dione 在 4-二甲氨基吡啶 、 过氧化双月桂酰 、 二苯基硅烷 、 N,N'-硫羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 11.5h， 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
• 作为产物：
  描述：

  在 manganese(IV) oxide 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 19-hydroxy-6-(tert-butoxycarbonyl)-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.