2-[[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]methylamino]propionic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]methylamino]propionic acid tert-butyl ester
• 英文别名: Tert-butyl 2-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl-methylamino]propanoate；tert-butyl 2-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl-methylamino]propanoate
• 化学式: C₁₈H₂₈BrNO₄
• 分子量: 402.329
• InChiKey: SNSLEDUZECHNEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]methylamino]propionic acid tert-butyl ester 在 tris(dibenzylideneacetone)dipalladium (0) 、 lithium tert-butoxide 、 (2'-(dimethylamino)biphenyl-2-yl)diphenylphosphine oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 45.0h， 以66%的产率得到6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

  摘要：

  The Pd-catalyzed intramolecular alpha-arylation of alpha-amino acid esters is described. Starting from readily available amino acids, the synthesis of a variety of isoindolines and tetrahydroisoquinoline carboxylic acid esters has been accomplished. Additionally, fused tricyclic systems can be efficiently prepared from cyclic amino acid esters. Reaction conditions have been found that allow the use of tert-butyl ester and N-(benzyloxycarbonyl) protecting groups.

  DOI：

  10.1021/jo0107756
• 作为产物：
  描述：

  2-溴丙酸叔丁酯 、 β-(2-bromo-4,5-dimethoxyphenyl)-N-methylethylamine 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 41.0h， 以66%的产率得到2-[[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]methylamino]propionic acid tert-butyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

  摘要：

  The Pd-catalyzed intramolecular alpha-arylation of alpha-amino acid esters is described. Starting from readily available amino acids, the synthesis of a variety of isoindolines and tetrahydroisoquinoline carboxylic acid esters has been accomplished. Additionally, fused tricyclic systems can be efficiently prepared from cyclic amino acid esters. Reaction conditions have been found that allow the use of tert-butyl ester and N-(benzyloxycarbonyl) protecting groups.

  DOI：

  10.1021/jo0107756

文献信息

• Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters
  作者：Oliver Gaertzen、Stephen L. Buchwald

  DOI：10.1021/jo0107756

  日期：2002.1.1

  The Pd-catalyzed intramolecular alpha-arylation of alpha-amino acid esters is described. Starting from readily available amino acids, the synthesis of a variety of isoindolines and tetrahydroisoquinoline carboxylic acid esters has been accomplished. Additionally, fused tricyclic systems can be efficiently prepared from cyclic amino acid esters. Reaction conditions have been found that allow the use of tert-butyl ester and N-(benzyloxycarbonyl) protecting groups.