(7S,8R,8aS)-7-ethyl-8-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-3-one | 926643-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (7S,8R,8aS)-7-ethyl-8-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-3-one
• 英文别名: (7S,8R,8aS)-7-ethyl-8-hydroxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 926643-68-7
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: GIEQZZDWEAEYPV-OYNCUSHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7S,8R,8aS)-7-ethyl-8-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以45%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：

  (7S,8S,8aS)-7-ethyl-8-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-3-one 在 三苯基膦 、 苯甲酸 、 偶氮二甲酸二乙酯 、 potassium carbonate 作用下， 以 甲苯 、 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以64%的产率得到(7S,8R,8aS)-7-ethyl-8-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-3-one
  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

文献信息

• An expedient synthesis of 7(S)-ethyl-8(R or S)-indolizidinols based on a thiophene reductive desulfurization
  作者：Štefan Marchalín、Jozefína Žúžiová、Katarína Kadlečíková、Peter Šafář、Peter Baran、Vincent Dalla、Adam Daïch

  DOI：10.1016/j.tetlet.2006.11.092

  日期：2007.1

  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.