2-(1,1-dideuteroallyl)-1,2,3,4-tetrahydroisoquinoline | 1422183-60-5

• 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: 2-(1,1-dideuteroallyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(1,1-dideuterioprop-2-enyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1422183-60-5
• 化学式: C₁₂H₁₅N
• 分子量: 175.242
• InChiKey: CUPYWQCUYQLHOH-MGVXTIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  四氢异喹啉 、 allyl-1,1-d2 acetate 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 2-(1,1-dideuteroallyl)-1,2,3,4-tetrahydroisoquinoline 、 2-(3,3-dideuteroallyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Achieving Control over the Branched/Linear Selectivity in Palladium-Catalyzed Allylic Amination

  摘要：

  Palladium-catalyzed reaction of unsymmetrical allylic electrophiles with amines gives rise to regioisomeric allylic amines. We have found that linear products result from the thermodynamically controlled isomerization of the initially formed branched products. The isomerization is promoted by protic acid and active palladium catalyst. The use of base shuts down the isomerization pathway and allows for the preparation and isolation of branched allylic amines. Solvent plays a key role in achieving high kinetic regioselectivity and in controlling the rate of isomerization. The isomerization can be combined with ring-closing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursors.

  DOI：

  10.1021/jo3025253

文献信息

• Achieving Control over the Branched/Linear Selectivity in Palladium-Catalyzed Allylic Amination
  作者：Igor Dubovyk、Iain D. G. Watson、Andrei K. Yudin

  DOI：10.1021/jo3025253

  日期：2013.2.15

  Palladium-catalyzed reaction of unsymmetrical allylic electrophiles with amines gives rise to regioisomeric allylic amines. We have found that linear products result from the thermodynamically controlled isomerization of the initially formed branched products. The isomerization is promoted by protic acid and active palladium catalyst. The use of base shuts down the isomerization pathway and allows for the preparation and isolation of branched allylic amines. Solvent plays a key role in achieving high kinetic regioselectivity and in controlling the rate of isomerization. The isomerization can be combined with ring-closing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursors.