methyl 7α,12α-diacetoxy-3α-(p-azidomethylphenyl)-3β-dicyanomethylcholan-24-oate | 134699-59-5

• 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: methyl 7α,12α-diacetoxy-3α-(p-azidomethylphenyl)-3β-dicyanomethylcholan-24-oate
• 英文别名: methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diacetyloxy-3-[4-(azidomethyl)phenyl]-3-(dicyanomethyl)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 134699-59-5
• 化学式: C₃₉H₅₁N₅O₆
• 分子量: 685.864
• InChiKey: XJQDYSNVDRPVEV-HIYMDVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 7α,12α-diacetoxy-3α-(p-azidomethylphenyl)-3β-dicyanomethylcholan-24-oate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Diacetoxy-3-(4-aminomethyl-phenyl)-3-dicyanomethyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of a new ‘cholaphane’ with externally directed functionality

  摘要：

  “胆酸酯（cholaphane）”是以26%的总产率从胆酸合成的，其结构通过X射线晶体学确定；该分子采用开放构象，并能够包围两个四氢呋喃分子。

  DOI：

  10.1039/c39910000612
• 作为产物：
  描述：

  methyl 7α,12α-diacetoxy-3-dicyanomethylenecholan-24-oate 在 N,N-二异丙基乙胺 、 tetramethylguanidinum azide 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 methyl 7α,12α-diacetoxy-3α-(p-azidomethylphenyl)-3β-dicyanomethylcholan-24-oate
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of a new ‘cholaphane’ with externally directed functionality

  摘要：

  “胆酸酯（cholaphane）”是以26%的总产率从胆酸合成的，其结构通过X射线晶体学确定；该分子采用开放构象，并能够包围两个四氢呋喃分子。

  DOI：

  10.1039/c39910000612

文献信息

• Synthesis of cyclo-bis[7α, 12α-diacetoxy-3β-dicyanomethyl-3α-(4-methylenephenyl)cholanamide]; a cholaphane with reduced flexibility and externally-directed functionality
  作者：Anthony P. Davis、Michael G. Orchard

  DOI：10.1039/p19930000919

  日期：——

  A second 'cholaphane' framework is manifested in the title compound 8, which has been prepared from methyl 3alpha, 7alpha, 12alpha-triacetoxycholanoate 9 in 23% overall yield. The synthesis involves the Knoevenagel condensation of ketone 11 with malononitrile to give dicyanomethylene derivative 12, equatorial-selective addition to the latter of an organocuprate derived from aryl bromide 1 5, conversion of the resulting adduct into amino acid 22, and cyclodimerisation. The framework of 8 has less conformational freedom and a better-defined cavity than the 'first-generation' cholaphanes 2, and also bears externally-directed functionality.