(1-ethyl-3,4-dihydro-1H-isoquinolin-2-yl)methyl-trimethylsilane | 144436-89-5

• 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: (1-ethyl-3,4-dihydro-1H-isoquinolin-2-yl)methyl-trimethylsilane
• CAS: 144436-89-5
• 化学式: C₁₅H₂₅NSi
• 分子量: 247.456
• InChiKey: BVXLVEUREOPFPY-UHFFFAOYSA-N

物化性质

• 沸点：
  295.0±25.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (1-ethyl-3,4-dihydro-1H-isoquinolin-2-yl)methyl-trimethylsilane 、 碘甲烷 以 乙腈 为溶剂， 反应 1.0h， 生成 (1R,2S)-1-Ethyl-2-methyl-2-trimethylsilanylmethyl-1,2,3,4-tetrahydro-isoquinolinium; iodide 、 (1R,2R)-1-Ethyl-2-methyl-2-trimethylsilanylmethyl-1,2,3,4-tetrahydro-isoquinolinium; 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
• 作为产物：
  描述：

  1-乙基-1,2,3,4-四氢异喹啉 、 碘甲基三甲基硅烷 以 二甲基亚砜 为溶剂， 反应 3.0h， 以60%的产率得到(1-ethyl-3,4-dihydro-1H-isoquinolin-2-yl)methyl-trimethylsilane
  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