2-allyl-4-methylene-1,2,3,4-tetrahydro-isoquinoline | 913711-42-9

• 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-allyl-4-methylene-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 4-Methylidene-2-prop-2-enyl-1,3-dihydroisoquinoline；4-methylidene-2-prop-2-enyl-1,3-dihydroisoquinoline
• CAS: 913711-42-9
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: LDXPITNRYGZJKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-allyl-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 2-allyl-3'-(3,5-dichloro-2,4,6-trimethylphenyl)-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：

  N-[(2-iodophenyl)methyl]-N-prop-2-enylprop-2-en-1-amine 在 palladium diacetate 、 三苯基膦 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-allyl-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

• Substrate controlled, regioselective carbopalladation for the one-pot synthesis of C4-substituted tetrahydroisoquinoline analogues
  作者：Singarajanahalli Mundarinti Krishna Reddy、Pavithira Suresh、Subbiah Thamotharan、Jagadeesh Babu Nanubolu、Surisetti Suresh、Subramaniapillai Selva Ganesan

  DOI：10.1039/d0ra01539c

  日期：——

  6-Exo-trig cyclization reaction through regioselective carbopalladation was demonstrated with N-(2-halobenzyl)-N-allylamines to furnish the corresponding C4-substituted tetrahydroisoquinoline derivatives. The scope of the reaction was extended to the synthesis of C4-quaternary tetrahydroisoquinoline derivatives also. The nature of the substituent on the olefin moiety dictates the course of the carbopalladation

  用N- (2-卤代苄基) -N-烯丙胺证明了通过区域选择性碳钯化的6 -Exo-trig环化反应以提供相应的 C4-取代的四氢异喹啉衍生物。该反应的范围也扩展到C4-季四氢异喹啉衍生物的合成。烯烃部分上取代基的性质决定了碳钯化顺序的过程。通过与不对称的二烯丙基化胺底物进行反应来证实区域选择性碳钯化。
• 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.