N-butyl-5,6-dimethoxyindoline | 139721-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-butyl-5,6-dimethoxyindoline
• 英文别名: 1-Butyl-5,6-dimethoxy-2,3-dihydroindole
• CAS: 139721-23-6
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: XJIIYYJNBAXOMF-UHFFFAOYSA-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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-Butyl-2-(2-chloro-4,5-dimethoxy-phenyl)-acetamide 在 ammonium sulfate 、 lithium aluminium tetrahydride 、 仲丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 生成 N-butyl-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

文献信息

• US5178637A
  申请人：——

  公开号：US5178637A

  公开（公告）日：1993-01-12
• 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
  作者：Thais M. Sielecki、A. I. Meyers

  DOI：10.1021/jo00039a029

  日期：1992.6

  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.