(5R,8S,11R,13S,14S)-17-bromo-11-(4-(dimethylamino)phenyl)-13-methyl-17-nitro-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-5(4H)-ol | 244304-96-9

• 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: (5R,8S,11R,13S,14S)-17-bromo-11-(4-(dimethylamino)phenyl)-13-methyl-17-nitro-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-5(4H)-ol
• CAS: 244304-96-9
• 化学式: C₂₈H₃₇BrN₂O₅
• 分子量: 561.516
• InChiKey: KPTYXVGTZJMPPM-MQRKGMRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.07
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5R,8S,11R,13S,14S)-17-bromo-11-(4-(dimethylamino)phenyl)-13-methyl-17-nitro-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-5(4H)-ol 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (5R,8S,11R,13S,14S,17S)-11-(4-(dimethylamino)phenyl)-13-methyl-17-nitro-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-5(4H)-ol
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Steroidal Acylaminoacetylenes:  Syntheses of Novel 11β-Aryl-17,17- spiro[(4‘H,5‘-methylene)oxazol]-Substituted Steroids

  摘要：

  A variety of novel 11 beta-aryl-17,17-spiro[(4'H,5'-methylene)oxazol]-substituted steroids have been synthesized in moderate to good yields via copper-catalyzed cyclization of acylaminoacetylenes. The best result was obtained with a catalytic amount of CuI in 1:1 benzene-Et3N at 90 degrees C for 30 min (Ar = 3,4-difluorophenyl; R = ethyl; 97% yield).

  DOI：

  10.1021/ol070447d
• 作为产物：
  描述：

  (5'R,8'S,11'R,13'S,14'S)-11'-[4-(dimethylamino)phenyl]-17'-hydroxyimino-13'-methylspiro[1,3-dioxolane-2,3'-2,4,6,7,8,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-5'-ol 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 (5R,8S,11R,13S,14S)-17-bromo-11-(4-(dimethylamino)phenyl)-13-methyl-17-nitro-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-5(4H)-ol
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Steroidal Acylaminoacetylenes:  Syntheses of Novel 11β-Aryl-17,17- spiro[(4‘H,5‘-methylene)oxazol]-Substituted Steroids

  摘要：

  A variety of novel 11 beta-aryl-17,17-spiro[(4'H,5'-methylene)oxazol]-substituted steroids have been synthesized in moderate to good yields via copper-catalyzed cyclization of acylaminoacetylenes. The best result was obtained with a catalytic amount of CuI in 1:1 benzene-Et3N at 90 degrees C for 30 min (Ar = 3,4-difluorophenyl; R = ethyl; 97% yield).

  DOI：

  10.1021/ol070447d