[1-(7-Benzyloxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((S)-1-tert-butoxymethyl-2-methyl-propyl)-amine | 123190-98-7

• 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-(7-Benzyloxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((S)-1-tert-butoxymethyl-2-methyl-propyl)-amine
• 英文别名: 1-(6-methoxy-7-phenylmethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-N-[(2S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]butan-2-yl]methanimine
• CAS: 123190-98-7
• 化学式: C₂₇H₃₈N₂O₃
• 分子量: 438.61
• InChiKey: DCKHTWQERWTUMM-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  43.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(7-Benzyloxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((S)-1-tert-butoxymethyl-2-methyl-propyl)-amine 在 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 188.17h， 生成 O-benzylcryptaustoline
  参考文献：
  名称：

  Formamidines in synthesis. An efficient one-pot synthesis of 7-substituted indolines via intramolecular cyclization of (2-phenethyl)formamidines. An asymmetric route to benzopyrrocoline alkaloids

  摘要：

  o-Chloro-beta-phenethylamines, transformed into the N-tert-butylformamidines, were found to be excellent precursors to indolines following benzyne formation. A series of methoxy-substituted o-chlorophenethylamines containing an N-alkyl or aryl substitutent were subjected to sec-butyllithium producing the ortho-lithiated aromatic which subsequently lost lithium chloride at temperatures ranging from -78 to -50-degrees-C. The resulting benzyne was intramolecularly trapped providing the titled heterocycles. Quenching the reaction resulted in elimination of the tert-butyl isocyanide (isolated after aqueous workup as tert-butylformamide) and protonation (or alkylation) of the 7-lithio position. Overall the yields for this process were 60-95% for a variety of N-substituted phenethylamines. In addition, a one-pot total asymmetric route to benzopyrrocoline alkaloids was featured using this benzyne trapping of chiral formamidines.

  DOI：

  10.1021/jo00039a029