(3aS,8aS,9R,9aS)-9-hydroxyoctahydrofuro[3,2-f]indolizin-6(2H)-one | 849177-58-8

• 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: (3aS,8aS,9R,9aS)-9-hydroxyoctahydrofuro[3,2-f]indolizin-6(2H)-one
• 英文别名: (3aS,8aS,9R,9aS)-9-hydroxyoctahydrofuro[3,2-f]indolizin-6(7H)-one；(3aS,8aS,9R,9aS)-9-Hydroxy-2,3,3a,7,8,8a,9,9a-octahydrofuro[3,2-f]indolizin-6(4H)-one；(3aS,8aS,9R,9aS)-9-hydroxy-3,3a,4,7,8,8a,9,9a-octahydro-2H-furo[3,2-f]indolizin-6-one
• CAS: 849177-58-8
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: XLDSIEAUGLXKQG-MFDQJXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,8aS,9R,9aS)-9-hydroxyoctahydrofuro[3,2-f]indolizin-6(2H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以77%的产率得到(3aS,8aS,9R,9aS)-9-hydroxydecahydrofuro[3,2-f]indolizine
  参考文献：
  名称：

  Highly diastereoselective approach to novel tetrahydrofuran-fused indolizidinols: a one-step formation of three contiguous stereocenters

  摘要：

  A concise and very efficient route to enantiopure tetrahydrofuran-fused indolizidinols, which could be considered as protected new indolizidindiols, is described in two-steps sequence starting from the known furoindolizidindiones. The key-step of these transformations was the formation, in one operation, of THF indolizidinols containing a lactam function by simultaneous highly diastereoseleclive catalytic hydrogenation of the carbonyl function and the furan ring. During these investigations, numerous catalysts in different combinations were tested and the impact of substrates on the reduction profile is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.013
• 作为产物：
  描述：

  C₁₀H₉NO₃ 在 Rh/Al₂O₃ 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、203.0 kPa 条件下， 反应 46.0h， 以76%的产率得到(3aS,8aS,9R,9aS)-9-hydroxyoctahydrofuro[3,2-f]indolizin-6(2H)-one
  参考文献：
  名称：

  Highly diastereoselective approach to novel tetrahydrofuran-fused indolizidinols: a one-step formation of three contiguous stereocenters

  摘要：

  A concise and very efficient route to enantiopure tetrahydrofuran-fused indolizidinols, which could be considered as protected new indolizidindiols, is described in two-steps sequence starting from the known furoindolizidindiones. The key-step of these transformations was the formation, in one operation, of THF indolizidinols containing a lactam function by simultaneous highly diastereoseleclive catalytic hydrogenation of the carbonyl function and the furan ring. During these investigations, numerous catalysts in different combinations were tested and the impact of substrates on the reduction profile is discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.013

文献信息

• Regioselective ring opening of the chiral non-racemic furoindolizidinols. New entry to alkylindolizidinediol derivatives
  作者：Peter Šafář、Jozefína Žúžiová、Eva Tóthová、Štefan Marchalín、Nadežda Prónayová、Ľubomír Švorc、Viktor Vrábel、Sébastien Comesse、Adam Daïch

  DOI：10.1016/j.tetasy.2010.03.018

  日期：2010.3

  New homochiral 6-ethyl-7,8-indolizidinediol derivatives, related to the bioactive dihydroxylated indolizidine alkaloids, are reported to be easily accessible in four or five steps from enantiopure 9-hydroxy-octahydrofuro[3,2-f]indolizin-6(2H)-ones in good overall yields and high diastereomeric purities. The simple procedure used herein involves a regiospecific THF-ring opening as a key step, in addition to the C-Br linkage reduction, and the alcohol deprotection followed by lactam reduction. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly diastereoselective approach to novel tetrahydrofuran-fused indolizidinols: a one-step formation of three contiguous stereocenters
  作者：Peter Šafář、Jozefína Žúžiová、Mária Bobošíková、Štefan Marchalín、Nadežda Prónayová、Vincent Dalla、Adam Daïch

  DOI：10.1016/j.tetasy.2008.01.013

  日期：2008.3

  A concise and very efficient route to enantiopure tetrahydrofuran-fused indolizidinols, which could be considered as protected new indolizidindiols, is described in two-steps sequence starting from the known furoindolizidindiones. The key-step of these transformations was the formation, in one operation, of THF indolizidinols containing a lactam function by simultaneous highly diastereoseleclive catalytic hydrogenation of the carbonyl function and the furan ring. During these investigations, numerous catalysts in different combinations were tested and the impact of substrates on the reduction profile is discussed. (C) 2008 Elsevier Ltd. All rights reserved.