2-methyl-1,2,3,4-tetrahydro(1-²H₁)isoquinoline

• 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-1,2,3,4-tetrahydro(1-²H₁)isoquinoline
• 英文别名: 1-deutero-2-methyl-1,2,3,4-tetrahydroisoquinoline；1-deuterio-2-methyl-3,4-dihydro-1H-isoquinoline
• 化学式: C₁₀H₁₃N
• 分子量: 148.212
• InChiKey: KYXSVGVQGFPNRQ-BNEYPBHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-methyl-3,4-dihydroisoquinolinium iodide 在 萘 、 lithium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.33h， 生成 2-methyl-1,2,3,4-tetrahydro(1-²H₁)isoquinoline
  参考文献：
  名称：

  Alkali Metal-mediated Synthesis of 1- and 4-Substituted N-Alkyl-1,2,3,4-tetrahydro- isoquinolines

  摘要：

  Reductive cleavage by electron transfer from Li or K metal of 1-alkoxy-substituted N-alkyltetrahydroisoquinolines led to the formation of organometallic derivatives. Quenching of these intermediates with electrophilic reagents afforded 1- or 4-substituted N-alkyl-1,2,3,4-tetrahydroisoquinolines, depending upon the nature of the metal.

  DOI：

  10.3987/com-03-9936

文献信息

• Activation of benzylic amines towards regioselective metallation by borane complex formation
  作者：Mark R. Ebden、Nigel S. Simpkins、David N.A. Fox

  DOI：10.1016/0040-4039(95)01797-l

  日期：1995.11

  Formation of borane complexes of N, N-dimethylbenzylamine 4 and N methyltetrahydroisoquinoline 1 facilitates regioselective metallation of these systems using BuLi, giving benzylic anions which react with a range of electrophiles.

  N，N-二甲基苄胺4和N甲基四氢异喹啉1的硼烷络合物的形成有助于使用BuLi对这些系统进行区域选择性金属化，从而得到可与一系列亲电试剂反应的苄基阴离子。
• Nucleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines
  作者：Kamal Singh、Paramjit Singh、Esha Sharma、Yadwinder Deol

  DOI：10.1055/s-0033-1341239

  日期：——

  The direct C-1 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines via coupling of alpha-amino carbanions derived from Lewis acid complexed tetrahydroisoquinolines and in situ generated arynes is described. This process provides an easy access to the title compounds and a new synthetic route to (+/-)-cryptostyline alkaloids.
• Alkali Metal-mediated Synthesis of 1- and 4-Substituted N-Alkyl-1,2,3,4-tetrahydro- isoquinolines
  作者：Ugo Azzena、Luisa Pisano、Mario Pittalis

  DOI：10.3987/com-03-9936

  日期：——

  Reductive cleavage by electron transfer from Li or K metal of 1-alkoxy-substituted N-alkyltetrahydroisoquinolines led to the formation of organometallic derivatives. Quenching of these intermediates with electrophilic reagents afforded 1- or 4-substituted N-alkyl-1,2,3,4-tetrahydroisoquinolines, depending upon the nature of the metal.