(+)-1-(α-phenylethyl)-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole | 474623-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (+)-1-(α-phenylethyl)-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole
• 英文别名: 3-[(1R)-1-phenylethyl]-4-oxa-3,8,11-triazatricyclo[6.3.0.02,6]undeca-1(11),9-diene
• CAS: 474623-11-5
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: YRDSAVHTWREXPB-LMWSTFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-1-(α-phenylethyl)-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以52%的产率得到(+)-7-amino-6,7-dihydro-6-hydroxymethyl-5H-pyrrolo[1,2-a]imidazole
  参考文献：
  名称：

  Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology

  摘要：

  N-Benzyl and (R)-N-(alpha-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cyclo-addition to give predominantly bridged-ring products. namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2a]pyridines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00404-0
• 作为产物：
  描述：

  1-allyl-2-hydroxymethylimidazole 在 manganese(IV) oxide 、 magnesium sulfate 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 (+)-1-(α-phenylethyl)-1,3a,4,8b-tetrahydro-3H-imidazo[1',2':1,2]pyrrolo[3,4-c]isoxazole
  参考文献：
  名称：

  Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology

  摘要：

  N-Benzyl and (R)-N-(alpha-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cyclo-addition to give predominantly bridged-ring products. namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2a]pyridines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00404-0

文献信息

• Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology
  作者：Diego Basso、Gianluigi Broggini、Daniele Passarella、Tullio Pilati、Alberto Terraneo、Gaetano Zecchi

  DOI：10.1016/s0040-4020(02)00404-0

  日期：2002.5

  N-Benzyl and (R)-N-(alpha-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cyclo-addition to give predominantly bridged-ring products. namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2a]pyridines. (C) 2002 Elsevier Science Ltd. All rights reserved.