2-methyl-4-methylene-1,2,3,4-tetrahydro-isoquinoline | 91131-88-3

• 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-methyl-4-methylene-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 1,2,3,4-Tetrahydro-N-methyl-4-methylenisochinolin；2-Methyl-4-methylidene-1,3-dihydroisoquinoline；2-methyl-4-methylidene-1,3-dihydroisoquinoline
• CAS: 91131-88-3
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: SANAEWSPTFOIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-4-methylene-1,2,3,4-tetrahydro-isoquinoline 、 3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3'-(3,5-dichloro-2,4,6-trimethylphenyl)-2-methyl-2,3-dihydro-spiro[isoquinoline-4(1H),5'(4'H)-isoxazole]
  参考文献：
  名称：

  New 4-Spiroannulated Tetrahydroisoquinolines by a One-Pot Sequential Procedure. Isolation and Characterization of σ-Alkylpalladium Heck Intermediates

  摘要：

  A simple and efficient entry to new tetrahydroisoquinolines 4-spiroannulated to a five-membered heterocyclic ring has been achieved starting from secondary N-allylamines and involving sequential 2-iodobenzylation/intramolecular Heck reaction/1,3-dipolar cycloaddition. A variety of Heck cyclization conditions were surveyed. When using Pd(PPh3)(4) as catalyst, stable sigma-alkylpalladium iodide complexes were isolated and characterizated.

  DOI：

  10.1021/ol061693c
• 作为产物：
  描述：

  2-碘苯甲基溴 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 TEA 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 2-methyl-4-methylene-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  New 4-Spiroannulated Tetrahydroisoquinolines by a One-Pot Sequential Procedure. Isolation and Characterization of σ-Alkylpalladium Heck Intermediates

  摘要：

  A simple and efficient entry to new tetrahydroisoquinolines 4-spiroannulated to a five-membered heterocyclic ring has been achieved starting from secondary N-allylamines and involving sequential 2-iodobenzylation/intramolecular Heck reaction/1,3-dipolar cycloaddition. A variety of Heck cyclization conditions were surveyed. When using Pd(PPh3)(4) as catalyst, stable sigma-alkylpalladium iodide complexes were isolated and characterizated.

  DOI：

  10.1021/ol061693c

文献信息

• New 4-Spiroannulated Tetrahydroisoquinolines by a One-Pot Sequential Procedure. Isolation and Characterization of σ-Alkylpalladium Heck Intermediates
  作者：Egle M. Beccalli、Gianluigi Broggini、Michela Martinelli、Norberto Masciocchi、Silvia Sottocornola

  DOI：10.1021/ol061693c

  日期：2006.9.1

  A simple and efficient entry to new tetrahydroisoquinolines 4-spiroannulated to a five-membered heterocyclic ring has been achieved starting from secondary N-allylamines and involving sequential 2-iodobenzylation/intramolecular Heck reaction/1,3-dipolar cycloaddition. A variety of Heck cyclization conditions were surveyed. When using Pd(PPh3)(4) as catalyst, stable sigma-alkylpalladium iodide complexes were isolated and characterizated.