17-benzoyloxy-5α-androst-2-en-3-yl triflate | 124643-31-8

• 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: 17-benzoyloxy-5α-androst-2-en-3-yl triflate
• 英文别名: 3-trifiloxy-17β-benzoyloxy-androst-2-ene；17β-benzyloxy-5α-androst-2-en-3-yl triflate；[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-(trifluoromethylsulfonyloxy)-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] benzoate
• CAS: 124643-31-8
• 化学式: C₂₇H₃₃F₃O₅S
• 分子量: 526.617
• InChiKey: HUTCBYJEKZQQAE-LVYWIKMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  三丁基乙烯基锡 、 17-benzoyloxy-5α-androst-2-en-3-yl triflate 在 四(三苯基膦)钯 叔丁基邻苯二酚 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以62%的产率得到17-benzoyloxy-3-vinyl-5α-androst-2-ene
  参考文献：
  名称：

  Direct and carbonylative vinylation of steroidal triflates in the presence of homogeneous palladium catalysts

  摘要：

  The palladium-catalyzed vinylation of several steroid 2-enyl- and 3,5-dienyl-3 triflates and estrone-3-triflate was systematically examined using vinyltributylstannane as a vinylating agent. In carbon monoxide atmosphere the insertion of a CO molecule took place and unsaturated ketones were obtained. In this way new steroid derivatives containing unsaturated side chain were produced which can sei ve as starting material for further functionalization of the steroid skeleton.

  DOI：

  10.1016/0039-128x(94)90100-7

文献信息

• Facile Synthesis of Steroidal Phenyl Ketones via Homogeneous Catalytic Carbonylation
  作者：Rita Skoda-Földes、Zoltán Székvölgyi、László Kollár、Zoltán Berente、Judit Horváth、Zoltán Tuba

  DOI：10.1016/s0040-4020(00)00241-6

  日期：2000.5

  Steroidal phenyl ketones were synthesised in high yields by palladium-catalysed carbonylation reactions of 17-iodo-androst-16-ene derivatives in the presence of NaBPh4 under mild reaction conditions. Alkenyl bromides or enol triflates gave lower yields in the same reaction.

  在温和的反应条件下，在NaBPh 4的存在下，钯催化的17-碘-雄烷-16-烯衍生物的羰基化反应可高产率地合成甾族苯基酮。在同一反应中，烯基溴化物或烯醇三氟甲磺酸酯的收率较低。
• ß-aryl and ß-vinyl-αß-didehydro-α-aminoacid derivatives through the palladium-catalysed reaction of aryl and vinyl triflates with methyl α-acetamidoacrylate
  作者：A. Arcadi、S. Cacchi、F. Marinelli、E. Morera、G. Ortar

  DOI：10.1016/s0040-4020(01)87897-2

  日期：1990.1