3-methoxy-17a-[N,N-(1'-methoxycarbonyl-1',4'-butanediyl)carboxamido]-13α-D-homoestra-1,3,5(10),17-tetraene | 1256271-94-9

• 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: 3-methoxy-17a-[N,N-(1'-methoxycarbonyl-1',4'-butanediyl)carboxamido]-13α-D-homoestra-1,3,5(10),17-tetraene
• CAS: 1256271-94-9
• 化学式: C₂₇H₃₅NO₄
• 分子量: 437.579
• InChiKey: AXVWJUKFVDZPGH-PPSGNBORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  32.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  一氧化碳 、 3-methoxy-17a-iodo-13α-D-homoestra-1,3,5(10),17-tetraene 、 L-脯氨酸甲酯盐酸盐 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、4.0 MPa 条件下， 反应 110.0h， 以76%的产率得到3-methoxy-17a-[N,N-(1'-methoxycarbonyl-1',4'-butanediyl)carboxamido]-13α-D-homoestra-1,3,5(10),17-tetraene
  参考文献：
  名称：

  Novel 13β- and 13α-d-homo steroids: 17a-carboxamido-d-homoestra-1,3,5(10),17-tetraene derivatives via palladium-catalyzed aminocarbonylations

  摘要：

  17a-Methoxycarbonyl- and 17a-carboxamido-D-homoestra-1,3,5(10),17-tetraene derivatives were synthesized by palladium-catalyzed carbonylation reactions of the corresponding 17a-iodo-D-homoestra-1,3,5(10),17-tetraene derivatives using methanol and various amines as O- and N-nucleophiles, respectively. Both the natural (13 beta) and the epi (13 alpha) series of compounds were isolated. The 17a-iodo-17-ene functionalities in the two 13-epimer series differ in reactivity. While the aminocarbonylations were practically complete in the 13 beta series in reasonable reaction time under mild conditions and high isolated yields were achieved, the corresponding 13 alpha-17a-iodo-17-ene substrate has shown decreased reactivity resulting in moderate to low yields. However, under high carbon monoxide pressure (40 bar) excellent yields call be obtained even in the 13 alpha series. The aminocarbonylation was completely chemoselective in both series, i.e., the corresponding 17a-carboxamido-17-ene derivatives were formed exclusively. (C) 2010 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2010.07.002