(9S,9aR)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one | 1415156-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (9S,9aR)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one
• 英文别名: (9S,9aR)-9-hydroxy-5,8,9,9a-tetrahydro-4H-furo[2,3-g]indolizin-7-one
• CAS: 1415156-94-3
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: WTNVCKQUTDWBSG-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基乙基呋喃 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟乙酸 、 potassium hydroxide 作用下， 以 吡啶 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 为溶剂， 反应 33.17h， 生成 (9S,9aR)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one
  参考文献：
  名称：

  Highly diastereoselective N-acyliminium ion cyclization reactions of a tethered furan

  摘要：

  The acid catalysed cyclization reactions of tethered furan-4,5-dihydroxypyrrolid-2-ones and furan-4,5-diacetoxypyrrolid-2-ones, via their corresponding N-acyliminium ion intermediates, have been studied. In the case of the tethered furan-3,4-dihydroxypyrrolid-2-one 16, having a two carbon tether, the linearly fused tricyclic compound 18 was formed with high cis selectivity (cis/trans=84:16) when BF3 center dot OEt2 was used as a catalyst. However, when the cyclization reaction was carried out on the related tethered furan-4,5-diacetoxypyrrolid-2-one 17, the linearly fused tricyclic compound 20 was formed as a single diastereoisomer with trans selectivity. In contrast, the attempted cyclization of the tethered furan-4,5-dihydroxypyrrolid-2-one 26, having a one carbon tether, did not result in formation of the corresponding linearly fused tricyclic system, instead it formed the dimer 29 as a single diastereoisomer. Cyclization reactions of the related tethered furan-4,5-diacetoxypyrrolid-2-one 27 also failed to give the corresponding linearly fused tricyclic system or macrocycle. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.014

文献信息

• Highly diastereoselective N-acyliminium ion cyclization reactions of a tethered furan
  作者：Sudhir R. Shengule、Gregory Ryder、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1016/j.tet.2012.10.014

  日期：2012.12

  The acid catalysed cyclization reactions of tethered furan-4,5-dihydroxypyrrolid-2-ones and furan-4,5-diacetoxypyrrolid-2-ones, via their corresponding N-acyliminium ion intermediates, have been studied. In the case of the tethered furan-3,4-dihydroxypyrrolid-2-one 16, having a two carbon tether, the linearly fused tricyclic compound 18 was formed with high cis selectivity (cis/trans=84:16) when BF3 center dot OEt2 was used as a catalyst. However, when the cyclization reaction was carried out on the related tethered furan-4,5-diacetoxypyrrolid-2-one 17, the linearly fused tricyclic compound 20 was formed as a single diastereoisomer with trans selectivity. In contrast, the attempted cyclization of the tethered furan-4,5-dihydroxypyrrolid-2-one 26, having a one carbon tether, did not result in formation of the corresponding linearly fused tricyclic system, instead it formed the dimer 29 as a single diastereoisomer. Cyclization reactions of the related tethered furan-4,5-diacetoxypyrrolid-2-one 27 also failed to give the corresponding linearly fused tricyclic system or macrocycle. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.