N-[(8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2,2,2-trifluoroacetamide | 940932-65-0

• 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: N-[(8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2,2,2-trifluoroacetamide
• CAS: 940932-65-0
• 化学式: C₃₀H₃₃F₃N₂O₂
• 分子量: 510.599
• InChiKey: YKQHQZWCWMAVIJ-DQFOBABISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2,2,2-trifluoroacetamide 在 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以63%的产率得到4',5'-dihydro-11β-[4-(N,N-dimethylamino)phenyl]-2'-trifluoromethyl-5'-methylenespiro[estra-4,9-dien-17β,4'-oxazol]-3-one
  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：

  (5alpha,10alpha)-5,10-环氧-雌甾-9(11)-烯-3,17-二酮环3-(1,2-乙二基缩醛) 在 FeSO₄(NH₄)2SO₄ 吡啶 、 盐酸 、 Sodium tetraborate decahydrate 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 4 A molecular sieve 、 盐酸羟胺 、 potassium tert-butylate 、 氯化铵 、 potassium hydrogencarbonate 、 三乙胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 N-[(8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2,2,2-trifluoroacetamide
  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

文献信息

• Copper-Catalyzed Cyclization of Steroidal Acylaminoacetylenes:  Syntheses of Novel 11β-Aryl-17,17- spiro[(4‘<i>H</i>,5‘-methylene)oxazol]-Substituted Steroids
  作者：Chunyang Jin、Jason P. Burgess、John A. Kepler、C. Edgar Cook

  DOI：10.1021/ol070447d

  日期：2007.5.1

  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).