(9S,9aS)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one | 1415156-93-2

• 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,9aS)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one
• 英文别名: (9S,9aS)-9-hydroxy-5,8,9,9a-tetrahydro-4H-furo[2,3-g]indolizin-7-one
• CAS: 1415156-93-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: WTNVCKQUTDWBSG-XVKPBYJWSA-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

• 作为反应物：
  描述：

  (9S,9aS)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以60%的产率得到(9S,9aS)-9-hydroxy-9,9a-dihydrofuro[2,3-g]indolizine-2,7(5H,8H)-dione
  参考文献：
  名称：

  对全合成生物碱生物碱水杨糖苷的模型支持研究

  摘要：

  本文中，我们报告了基于呋喃的方法通过线性稠合的三环中间体3合成口气碱生物碱，草体尿素1的结果，代表了目标分子的关键A，B，C环结构特征。从3-糠醛6开始，以涉及的合成顺序，对化合物3进行了高度非对映选择性的合成。（1）O的快速原位转换-在相邻的3-呋喃基的帮助下，构型反转而使甲磺酸酯化为相应的氯化物；（2）通过分子内氮杂-维蒂希反应制备氮杂ze环；（3）碱促进的内酰胺环形成步骤。建立了将3的呋喃环氧化为相应的γ-羟基-α，β-不饱和内酯的方法时，我们无法影响内酰胺环羟基环化成内酯的γ位以形成环醚特征天然产物。模型研究也没有成功。

  DOI：

  10.1016/j.tet.2013.06.099
• 作为产物：
  描述：

  2-氨基乙基呋喃 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 为溶剂， 反应 17.17h， 生成 (9S,9aS)-9-hydroxy-4,5,9,9a-tetrahydrofuro[2,3-g]indolizin-7(8H)-one 、 (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

• Model support studies toward the total synthesis of the stemona alkaloid stemocurtisine
  作者：Sudhir R. Shengule、Anthony C. Willis、Stephen G. Pyne

  DOI：10.1016/j.tet.2013.06.099

  日期：2013.9

  Herein we report the results of a furan-based approach toward the synthesis of the Stemona alkaloid, stemocurtisine 1 via the linearly fused tricyclic intermediate 3, representing the key A,B,C-ring structural feature of the target molecule. A highly diastereoselective synthesis of compound 3 was achieved starting from 3-furfural 6, in a synthetic sequence that involved; (1) a rapid in situ conversion

  本文中，我们报告了基于呋喃的方法通过线性稠合的三环中间体3合成口气碱生物碱，草体尿素1的结果，代表了目标分子的关键A，B，C环结构特征。从3-糠醛6开始，以涉及的合成顺序，对化合物3进行了高度非对映选择性的合成。（1）O的快速原位转换-在相邻的3-呋喃基的帮助下，构型反转而使甲磺酸酯化为相应的氯化物；（2）通过分子内氮杂-维蒂希反应制备氮杂ze环；（3）碱促进的内酰胺环形成步骤。建立了将3的呋喃环氧化为相应的γ-羟基-α，β-不饱和内酯的方法时，我们无法影响内酰胺环羟基环化成内酯的γ位以形成环醚特征天然产物。模型研究也没有成功。
• 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.