(7S,8R,8aS)-7-ethyl-8-phenylmethoxy-1,2,3,5,6,7,8,8a-octahydroindolizine | 926643-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (7S,8R,8aS)-7-ethyl-8-phenylmethoxy-1,2,3,5,6,7,8,8a-octahydroindolizine
• CAS: 926643-73-4
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: HNTQDSUSYRLFFY-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7S,8R,8aS)-7-ethyl-8-phenylmethoxy-1,2,3,5,6,7,8,8a-octahydroindolizine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以58%的产率得到(7S,8R,8aS)-7-ethyl-1,2,3,5,6,7,8,8a-octahydroindolizin-8-ol
  参考文献：
  名称：

  An expedient synthesis of 7(S)-ethyl-8(R or S)-indolizidinols based on a thiophene reductive desulfurization

  摘要：

  Chiral hexahydrothieno[2,3-f]indolizine-4,7-dione (S)-12 and the ancillary alcohol 13 were generated from thiophene-2-carboxaldehyde and (S)-glutamic acid in three and four steps, respectively, in good overall yields and both high enantio- and diastereomeric purities. Applying a thiophene reductive desulturization, compound 12 was readily converted into 7(S)-ethyl-8(S)-indolizidinol 9. The 8(R)-epimer of 9 was advantageously obtained using the Mitsunobu alcohol inversion or, starting from 13, by chemical separation after O-benzylation and lactam reduction. During these studies, the reduction of regioisomers of 12 and 13, namely 17 and 18, was investigated and the results obtained are also discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.092
• 作为产物：
  描述：

  (8R,8aS)-7-ethyl-8-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-3-one 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (7S,8R,8aS)-7-ethyl-8-phenylmethoxy-1,2,3,5,6,7,8,8a-octahydroindolizine
  参考文献：
  名称：

  An expedient synthesis of 7(S)-ethyl-8(R or S)-indolizidinols based on a thiophene reductive desulfurization

  摘要：

  Chiral hexahydrothieno[2,3-f]indolizine-4,7-dione (S)-12 and the ancillary alcohol 13 were generated from thiophene-2-carboxaldehyde and (S)-glutamic acid in three and four steps, respectively, in good overall yields and both high enantio- and diastereomeric purities. Applying a thiophene reductive desulturization, compound 12 was readily converted into 7(S)-ethyl-8(S)-indolizidinol 9. The 8(R)-epimer of 9 was advantageously obtained using the Mitsunobu alcohol inversion or, starting from 13, by chemical separation after O-benzylation and lactam reduction. During these studies, the reduction of regioisomers of 12 and 13, namely 17 and 18, was investigated and the results obtained are also discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.092