(3E,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-(nitromethylidene)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene | 1423157-20-3

• 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: (3E,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-(nitromethylidene)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene
• CAS: 1423157-20-3
• 化学式: C₂₈H₄₇NO₂
• 分子量: 429.687
• InChiKey: WMFYZSTXJWBDRZ-IVGPQMFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Methylen-5α-cholestan 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以78%的产率得到(3E,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-(nitromethylidene)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene
  参考文献：
  名称：

  A Predictably Selective Nitration of Olefin with Fe(NO₃)₃ and TEMPO

  摘要：

  Ferric nitrate with catalytic TEMPO has been identified as a useful reagent for regio- and stereoselective nitration of a wide variety of aromatic, aliphatic, and heteroaromatic olefins. This reaction provided nitroolefins in preparatively useful yields with excellent E-selectivity. Due to its mild nature and operational simplicity, the present protocol is expected to find application in synthetic setup.

  DOI：

  10.1021/jo400598p