1-(2-iodo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline | 303744-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-(2-iodo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 1-(2-Iodophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 303744-14-1
• 化学式: C₁₇H₁₈INO₂
• 分子量: 395.24
• InChiKey: OKFGOUZTQYXOPO-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±45.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙二烯 、 1-(2-iodo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 以91%的产率得到2,3-dimethoxy-9-methylene-6,8,9,13b-tetrahydro-5H-isoquino[1,2-a]isoquinoline
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1
• 作为产物：
  描述：

  [2-(3,4-dimethoxy-phenyl)-ethyl]-(2-iodo-benzylidene)amine 在 三氟乙酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以89%的产率得到1-(2-iodo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1

文献信息

• Silver- and Gold-Mediated Intramolecular Cyclization to Substituted Tetracyclic Isoquinolizinium Hexafluorostilbates
  作者：Fang Liu、Xiao Ding、Lei Zhang、Yu Zhou、Linxiang Zhao、Hualiang Jiang、Hong Liu

  DOI：10.1021/jo1006174

  日期：2010.9.3

  A convenient route for the synthesis of various charged tetracyclic isoquinolizinium hexafluorostilbates was developed using AgSbF6/AuCl(PPh3) for the intramolecular addition of amine to alkyne. The described process is tolerant of a variety of functional groups and broadens the diversity of substrates with the use of 8-substituted tetracyclic isoquinolizinium salts.
• Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan、Mark Thornton-Pett、Jin Zhang

  DOI：10.1016/s0040-4020(00)00628-1

  日期：2000.8

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.