1,2,3,4-tetrahydro-(3S)-phenyl-N-methylisoquinoline

• 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: 1,2,3,4-tetrahydro-(3S)-phenyl-N-methylisoquinoline
• 英文别名: (3S)-2-methyl-3-phenyl-3,4-dihydro-1H-isoquinoline
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: OMCQQXLHQWYOSE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N,N-二乙基-2-甲基苯甲酰胺 、 N-methyl-1-phenylmethanimine 在 正丁基锂 、 鹰爪豆碱 、 dimethyl sulfide borane 作用下， 以 正己烷 、 甲苯 、 乙醚 、 四氢呋喃 为溶剂， 反应 2.5h， 生成 1,2,3,4-tetrahydro-(3S)-phenyl-N-methylisoquinoline 、 1,2,3,4-tetrahydro-(3R)-phenyl-N-methylisoquinoline
  参考文献：
  名称：

  Condensation of Laterally Lithiated o-Methyl and o-Ethyl Benzamides with Imines Mediated by (−)-Sparteine. Enantioselective Synthesis of Tetrahydroisoquinolin-1-ones

  摘要：

  The first asymmetric synthesis of tetrahydroisoquinolin-1-ones using a (-)-sparteine-mediated lateral metalation-imine addition sequence to furnish 3-phenyl tetrahydroisoquinolinones 3a with enantioselectivities up to 81% ee is described (Scheme 4). For amide 7b, imine addition products 10 and 11 have been obtained with high diastereoselectivities (91-97% de) and enantioselectivities (91-98% ee) (Scheme 8).

  DOI：

  10.1021/jo001369+

文献信息

• Condensation of Laterally Lithiated <i>o</i>-Methyl and <i>o</i>-Ethyl Benzamides with Imines Mediated by (−)-Sparteine. Enantioselective Synthesis of Tetrahydroisoquinolin-1-ones
  作者：Volker Derdau、Victor Snieckus

  DOI：10.1021/jo001369+

  日期：2001.3.1

  The first asymmetric synthesis of tetrahydroisoquinolin-1-ones using a (-)-sparteine-mediated lateral metalation-imine addition sequence to furnish 3-phenyl tetrahydroisoquinolinones 3a with enantioselectivities up to 81% ee is described (Scheme 4). For amide 7b, imine addition products 10 and 11 have been obtained with high diastereoselectivities (91-97% de) and enantioselectivities (91-98% ee) (Scheme 8).