3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxamide
• 英文别名: (1S,2R,3S,4R)-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxamide
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: TTWXSENPKHNTJG-BGPJRJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.34
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以77%的产率得到di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-methanamine
  参考文献：
  名称：

  Preparation and structure of pyrrolo[2,1-b]- and isoindolo[1,2-b][3,1]epoxyquinazolines

  摘要：

  Various gamma-oxocarboxylic acids [aroylpropionic acids, cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid, diendo-3-benzoylbicyclo[2.2.1] heptane-2-carboxylic acid, formylbenzoic acid, methanobenzenecyclooctencarboxylic acid and the cyclopentadiene adduct of 3-trans-(4-methylbenzoyl)acrylic acid] were reacted with diexo-3-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ylamine 2 to result in condensed pyrroloepoxyquinazolines 3-10. The starting 2 retained the diexo configuration, but cis -> trans isomerization took place when cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid was applied. The structures, including the ring annelations and the position of the aryl group on the new chiral centre, were established by means of NMR spectroscopy, and in the cases of the trans-3-(4-methylbenzoyl)acrylic acid-cyclopentadiene adduct for 10a, 10b and 10c by X-ray crystallography. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.07.019
• 作为产物：
  描述：

  ethyl (1S,2R,3S,4R)-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 生成 3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxamide
  参考文献：
  名称：

  Preparation and structure of pyrrolo[2,1-b]- and isoindolo[1,2-b][3,1]epoxyquinazolines

  摘要：

  Various gamma-oxocarboxylic acids [aroylpropionic acids, cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid, diendo-3-benzoylbicyclo[2.2.1] heptane-2-carboxylic acid, formylbenzoic acid, methanobenzenecyclooctencarboxylic acid and the cyclopentadiene adduct of 3-trans-(4-methylbenzoyl)acrylic acid] were reacted with diexo-3-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ylamine 2 to result in condensed pyrroloepoxyquinazolines 3-10. The starting 2 retained the diexo configuration, but cis -> trans isomerization took place when cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid was applied. The structures, including the ring annelations and the position of the aryl group on the new chiral centre, were established by means of NMR spectroscopy, and in the cases of the trans-3-(4-methylbenzoyl)acrylic acid-cyclopentadiene adduct for 10a, 10b and 10c by X-ray crystallography. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.07.019

文献信息

• Continuous-Flow retro-Diels-Alder Reaction: A Process Window for Designing Heterocyclic Scaffolds
  作者：Imane Nekkaa、Márta Palkó、István M. Mándity、Ferenc Miklós、Ferenc Fülöp

  DOI：10.1002/ejoc.201800682

  日期：2018.8.31

  An approach based on a highly controlled continuous‐flow (CF) retro‐Diels–Alder reaction was developed for the synthesis of new compounds. Using this approach, we were able to rapidly screen reaction conditions to obtain the desired pyrimidinone moieties in short reaction times and high yields. We also present an alternative route for the synthesis of intermediates by CF cyclization.

  开发了一种基于高度受控的连续流（CF）Retro-Diels-Alder反应的方法来合成新化合物。使用这种方法，我们能够在短的反应时间和高收率下快速筛选反应条件以获得所需的嘧啶酮部分。我们还提出了一种通过CF环化合成中间体的替代途径。
• Preparation and structure of pyrrolo[2,1-b]- and isoindolo[1,2-b][3,1]epoxyquinazolines
  作者：Iván Kanizsai、Ferenc Miklós、Pál Sohár、Antal Csámpai、Reijo Sillanpää、Géza Stájer

  DOI：10.1016/j.molstruc.2006.07.019

  日期：2007.4

  Various gamma-oxocarboxylic acids [aroylpropionic acids, cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid, diendo-3-benzoylbicyclo[2.2.1] heptane-2-carboxylic acid, formylbenzoic acid, methanobenzenecyclooctencarboxylic acid and the cyclopentadiene adduct of 3-trans-(4-methylbenzoyl)acrylic acid] were reacted with diexo-3-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ylamine 2 to result in condensed pyrroloepoxyquinazolines 3-10. The starting 2 retained the diexo configuration, but cis -> trans isomerization took place when cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid was applied. The structures, including the ring annelations and the position of the aryl group on the new chiral centre, were established by means of NMR spectroscopy, and in the cases of the trans-3-(4-methylbenzoyl)acrylic acid-cyclopentadiene adduct for 10a, 10b and 10c by X-ray crystallography. (c) 2006 Elsevier B.V. All rights reserved.