N-(1-benzyloxyallyl)-N-methylacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-benzyloxyallyl)-N-methylacetamide
• 英文别名: N-methyl-N-(1-phenylmethoxyprop-2-enyl)acetamide
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: XQXKYDIPOYEKFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基乙酰胺 、 1-benzyloxyallene 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 64.0h， 以21%的产率得到N-(1-benzyloxyallyl)-N-methylacetamide
  参考文献：
  名称：

  Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid

  摘要：

  A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I.

  DOI：

  10.1021/ja039919j

文献信息

• Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid
  作者：Sape S. Kinderman、René de Gelder、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra、Floris P. J. T. Rutjes

  DOI：10.1021/ja039919j

  日期：2004.4.1

  A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I.