(8R,9S,13S,14S)-3-methoxy-13-methyl-17-[4-tri(propan-2-yl)silylbuta-1,3-diynyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol | 1257092-60-6

• 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: (8R,9S,13S,14S)-3-methoxy-13-methyl-17-[4-tri(propan-2-yl)silylbuta-1,3-diynyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS: 1257092-60-6
• 化学式: C₃₂H₄₆O₂Si
• 分子量: 490.802
• InChiKey: OBBHYEWOCSUHTN-BJPJELPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S)-3-methoxy-13-methyl-17-[4-tri(propan-2-yl)silylbuta-1,3-diynyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol 、 苄基叠氮 在 四丁基氟化铵 、 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到(8R,9S,13S,14S)-17-[2-(1-benzyltriazol-4-yl)ethynyl]-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Reactions of Terminal Polyynes with Benzyl Azide

  摘要：

  Terminal di-, tri-, tetra-, and pentaynes substituted with a variety of functional groups react with benzyl azide in the presence of CuSO4 center dot 5H(2)O and ascorbic acid to give derivatives of 4-ethynyl-, 4-butadiynyl-, 4-hexatriynyl-, and 4-octatetraynyl-,2,3-triazoles in moderate to good yields. These reactions appear to proceed regioselectively, and functionalization occurs exclusively at the terminal alkyne moiety. As well, no evidence of multiple azide additions to the polyyne framework is observed. X-ray crystallographic analysis of nine derivatives is used to document the regioselectivity of the reaction as well as outline structural characteristics of the 1,2,3-triazole products.

  DOI：

  10.1021/jo101870y
• 作为产物：
  描述：

  3-甲氧基雌酮 、 1,1-dibromo-4-(triisopropylsilyl)but-1-en-3-yne 在 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以93%的产率得到(8R,9S,13S,14S)-3-methoxy-13-methyl-17-[4-tri(propan-2-yl)silylbuta-1,3-diynyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Reactions of Terminal Polyynes with Benzyl Azide

  摘要：

  Terminal di-, tri-, tetra-, and pentaynes substituted with a variety of functional groups react with benzyl azide in the presence of CuSO4 center dot 5H(2)O and ascorbic acid to give derivatives of 4-ethynyl-, 4-butadiynyl-, 4-hexatriynyl-, and 4-octatetraynyl-,2,3-triazoles in moderate to good yields. These reactions appear to proceed regioselectively, and functionalization occurs exclusively at the terminal alkyne moiety. As well, no evidence of multiple azide additions to the polyyne framework is observed. X-ray crystallographic analysis of nine derivatives is used to document the regioselectivity of the reaction as well as outline structural characteristics of the 1,2,3-triazole products.

  DOI：

  10.1021/jo101870y