2-methyl-2-<(trimethylsilyl)methyl>-1,2,3,4-tetrahydroisoquinolinium iodide | 134753-82-5

• 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-methyl-2-<(trimethylsilyl)methyl>-1,2,3,4-tetrahydroisoquinolinium iodide
• 英文别名: 2-methyl-2-[(trimethylsilyl)methyl]-1,2,3,4-tetrahydroisoquinolinium iodide；trimethyl-[(2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl)methyl]silane;iodide
• CAS: 134753-82-5
• 化学式: C₁₄H₂₄NSi*I
• 分子量: 361.341
• InChiKey: JOUOMYJUVXKSDR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-2-<(trimethylsilyl)methyl>-1,2,3,4-tetrahydroisoquinolinium iodide 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以34%的产率得到2-methyl-1-<(trimethylsilyl)methyl>-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Rearrangements of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides

  摘要：

  Chemical behavior of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides 4 was investigated in fluoride-ion induced desilylation reaction of 1,6,7-trisubstituted 2-methyl-2-(trimethylsilyl)-methyl-1,2,3,4-tetrahydroisoquinolinium iodides 3. The 1-nonsubstituted (4a,b) and 1-alkyl-substituted ylides (4c,d) gave mixtures of five products (7-11), but the 1-phenyl-substituted analogues (4e,f) yielded (E)- and (Z)-2,3-disubstituted 5-benzylidene-1,3-cyclohexadiene-6-spiro-3'-1'-methylpyrrolidines (E)-5 and (Z)-5 and 7,8-disubstituted 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6. The mechanisms of the rearrangement are discussed.

  DOI：

  10.1021/jo00051a008
• 作为产物：
  描述：

  2-((trimethylsilyl)methyl)-1,2,3,4-tetrahydroisoquinoline 、 碘甲烷 以 乙腈 为溶剂， 反应 0.5h， 以94%的产率得到2-methyl-2-<(trimethylsilyl)methyl>-1,2,3,4-tetrahydroisoquinolinium iodide
  参考文献：
  名称：

  Rearrangements of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides

  摘要：

  Chemical behavior of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides 4 was investigated in fluoride-ion induced desilylation reaction of 1,6,7-trisubstituted 2-methyl-2-(trimethylsilyl)-methyl-1,2,3,4-tetrahydroisoquinolinium iodides 3. The 1-nonsubstituted (4a,b) and 1-alkyl-substituted ylides (4c,d) gave mixtures of five products (7-11), but the 1-phenyl-substituted analogues (4e,f) yielded (E)- and (Z)-2,3-disubstituted 5-benzylidene-1,3-cyclohexadiene-6-spiro-3'-1'-methylpyrrolidines (E)-5 and (Z)-5 and 7,8-disubstituted 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6. The mechanisms of the rearrangement are discussed.

  DOI：

  10.1021/jo00051a008

文献信息

• Rearrangements of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides
  作者：Yoshiro Sato、Naohiro Shirai、Yoshio Machida、Emiko Ito、Takayo Yasui、Yukihisa Kurono、Keiichiro Hatano

  DOI：10.1021/jo00051a008

  日期：1992.12

  Chemical behavior of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides 4 was investigated in fluoride-ion induced desilylation reaction of 1,6,7-trisubstituted 2-methyl-2-(trimethylsilyl)-methyl-1,2,3,4-tetrahydroisoquinolinium iodides 3. The 1-nonsubstituted (4a,b) and 1-alkyl-substituted ylides (4c,d) gave mixtures of five products (7-11), but the 1-phenyl-substituted analogues (4e,f) yielded (E)- and (Z)-2,3-disubstituted 5-benzylidene-1,3-cyclohexadiene-6-spiro-3'-1'-methylpyrrolidines (E)-5 and (Z)-5 and 7,8-disubstituted 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6. The mechanisms of the rearrangement are discussed.