di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-methanamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-methanamine
• 英文别名: 2-aminomethyl-7-oxabicyclo[2.2.1]hept-5-enyl-3-amine；(1S,2R,3S,4R)-3-(aminomethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-amine
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: PTOUHLZIXLFYRU-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-ene-2-methanamine 、 3-(4-氯苯甲酰)丙酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以20%的产率得到octahydro-3a-(4-chlorophenyl)-diexo-5,8-epoxypyrrolo[2,1-b]quinazolin-1-one
  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：

  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

文献信息

• Sohar, Pat; Csampai, Antal; Sillanpaeae, Reijo, Heterocycles, 2007, vol. 71, # 6, p. 1315 - 1326
  作者：Sohar, Pat、Csampai, Antal、Sillanpaeae, Reijo、Fueloep, Ferenc、Stajer, Geza

  DOI：——

  日期：——
• 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.