N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene | 195830-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene
• 英文别名: (1R,4S)-2-[(2-iodophenyl)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS: 195830-50-3
• 化学式: C₁₃H₁₂INO
• 分子量: 325.149
• InChiKey: GWPPFBFDQVEGRB-KOLCDFICSA-N

物化性质

• 沸点：
  450.5±45.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  四苯硼钠 、 N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene 在 palladium diacetate 四乙基氯化铵 、 三苯基膦 作用下， 以 苯甲醚 为溶剂， 反应 24.0h， 以43%的产率得到
  参考文献：
  名称：

  Palladium catalysed tandem cyclisation-anion capture processes. Part 3. Organoboron anion transfer agents

  摘要：

  The cyclisation-anion capture protocol has been applied to a wide range of starter and terminating species to effect regio-and stereo-specific mono-and bis-cyclisation processes in which a variety of organoboronderivatives function as anion transfer reagents. Direct capture (no cyclisation) is rarely a problem and it can usually be suppressed by modification of the reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00754-0
• 作为产物：
  描述：

  邻碘氯苄 、 (-)-文斯内酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以53%的产率得到N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  Palladium catalysed tandem cyclisation-anion capture processes. Part 3. Organoboron anion transfer agents

  摘要：

  The cyclisation-anion capture protocol has been applied to a wide range of starter and terminating species to effect regio-and stereo-specific mono-and bis-cyclisation processes in which a variety of organoboronderivatives function as anion transfer reagents. Direct capture (no cyclisation) is rarely a problem and it can usually be suppressed by modification of the reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00754-0

文献信息

• Palladium Catalysed Tandem Cyclisation–Anion Capture Processes. Part 4: Organotin(IV) Transfer Agents
  作者：Paul Fretwell、Ronald Grigg、Jose M Sansano、Visuvanathar Sridharan、Sukanthini Sukirthalingam、David Wilson、James Redpath

  DOI：10.1016/s0040-4020(00)00659-1

  日期：2000.9

  Palladium(0) catalysed cascade mono- and bis-cyclisation-anion capture involving a wide variety of starter species, terminating species and organotin(IV) anion capture reagents are reported leading to a range of bridged, fused and spirocyclic products. The diastereoselectivity of the bis-cyclisation processes is explained in terms of steric effects in the transition states. (C) 2000 Elsevier Science Ltd. All rights reserved.