(5R,11aS)-2-(5-azidopentyl)-5-(3-benzoyloxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione | 1223077-76-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (5R,11aS)-2-(5-azidopentyl)-5-(3-benzoyloxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione
• CAS: 1223077-76-6
• 化学式: C₃₁H₂₈N₆O₄
• 分子量: 548.601
• InChiKey: WZZXOJZSLBMELM-XTEPFMGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  131.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5R,11aS)-2-(5-azidopentyl)-5-(3-benzoyloxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到(5R,11aS)-2-(5-azido-pentyl)-5-(3-hydroxyphenyl)-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carboline-1,3-dione
  参考文献：
  名称：

  The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

  摘要：

  A general method for the synthesis of the mitotic kinesin Eg5 inhibitor HR22C16 1 and its analogues based on protecting group (PG)-modulated highly diastereoselective Pictet-Spengler reaction of L-tryptophan methyl ester hydrochloride with meta-(RO)-benzaldehyde is described. By using the enantiomerically pure (1R,3S)-1,3-disubstituted tetrahydro-beta-carboline trans-4c as a common chiral synthon, HR22C16 1 and its analogues 2 and 3 were synthesized in 90.1%, 90.2%, and 86.5% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.029
• 作为产物：
  描述：

  (1R,3S)-methyl 1-(3-(benzoyloxy)phenyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 、 1-叠氮基-5-氨基戊烷 在 三光气 、 三乙胺 、 盐酸 作用下， 以 二氯甲烷 、 甲苯 、 水 为溶剂， 反应 0.52h， 以93%的产率得到(5R,11aS)-2-(5-azidopentyl)-5-(3-benzoyloxyphenyl)-6H-1,2,3,5,11,11a-hexahydroimidazo[1,5-b]-β-carboline-1,3-dione
  参考文献：
  名称：

  The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

  摘要：

  A general method for the synthesis of the mitotic kinesin Eg5 inhibitor HR22C16 1 and its analogues based on protecting group (PG)-modulated highly diastereoselective Pictet-Spengler reaction of L-tryptophan methyl ester hydrochloride with meta-(RO)-benzaldehyde is described. By using the enantiomerically pure (1R,3S)-1,3-disubstituted tetrahydro-beta-carboline trans-4c as a common chiral synthon, HR22C16 1 and its analogues 2 and 3 were synthesized in 90.1%, 90.2%, and 86.5% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.029