3-(4'-methoxybenzyl)-5-vinyl-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4'-methoxybenzyl)-5-vinyl-1,3-oxazolidin-2-one
• 英文别名: 5-Ethenyl-3-[(4-methoxyphenyl)methyl]-1,3-oxazolidin-2-one；5-ethenyl-3-[(4-methoxyphenyl)methyl]-1,3-oxazolidin-2-one
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: MLKJMJMJTXXFCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-甲氧基苄基)2-丙炔基-1-基胺 1盐酸盐 在 盐酸 、 [(1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene)AgOAc] 、 二异丙胺 、 copper(I) bromide 作用下， 以 乙醚 、 水 、 异丙醇 、 甲苯 为溶剂， 30.0 ℃ 、1.0 MPa 条件下， 反应 31.0h， 生成 3-(4'-methoxybenzyl)-5-vinyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts

  摘要：

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.

  DOI：

  10.1021/acs.orglett.5b00809

文献信息

• Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
  作者：Kyohei Yamashita、Shun Hase、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1021/acs.orglett.5b00809

  日期：2015.5.15

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.