N-isopropyl-4-chloro-5,6-dimethoxyindoline | 141438-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-isopropyl-4-chloro-5,6-dimethoxyindoline
• 英文别名: 4-chloro-5,6-dimethoxy-1-propan-2-yl-2,3-dihydroindole
• CAS: 141438-39-3
• 化学式: C₁₃H₁₈ClNO₂
• 分子量: 255.744
• InChiKey: YIOGWCVEXHIOFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-isopropyl-N-<(2,6-dichloro-4,5-dimethoxyphenyl)ethyl>-N'-tert-butylformamidine 在 仲丁基锂 、 lithium bromide 作用下， 生成 N-isopropyl-4-chloro-5,6-dimethoxyindoline
  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