ethyl (3S,6RS)-6-[(2S)-2-tert-butoxycarbonylamino-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate | 832111-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (3S,6RS)-6-[(2S)-2-tert-butoxycarbonylamino-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate
• 英文别名: ethyl (3S)-8-cyano-6-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-5-oxo-2,3,6,7-tetrahydro-1H-indolizine-3-carboxylate
• CAS: 832111-39-4
• 化学式: C₂₂H₃₂N₄O₆
• 分子量: 448.519
• InChiKey: YIFVDNVRDRVZMM-HGVHAKBWSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  668.8±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  137.83
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl (3S,6RS)-6-[(2S)-2-tert-butoxycarbonylamino-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate 、 三氟乙酸 反应 2.25h， 以74%的产率得到ethyl (3S,6RS)-6-[(2S)-2-amino-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate trifluoroacetate
  参考文献：
  名称：

  Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters

  摘要：

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.036
• 作为产物：
  描述：

  ethyl (3S)-6-chloroacetylamino-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate 在 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 邻苯二胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 ethyl (3S,6RS)-6-[(2S)-2-tert-butoxycarbonylamino-3-methylbutanamido]-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate
  参考文献：
  名称：

  Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters

  摘要：

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.036