2-(1'-methoxyvinyl)-1,3-diphenyl-1,3-imidazolidine | 1186100-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 2-(1'-methoxyvinyl)-1,3-diphenyl-1,3-imidazolidine
• 英文别名: 2-(1-methoxyvinyl)-1,3-diphenylimidazolidine
• CAS: 1186100-70-8
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: OYFUIRKYVVYEJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  15.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(1'-methoxyvinyl)-1,3-diphenyl-1,3-imidazolidine 在 对甲苯磺酸 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 以41%的产率得到1-(1,3-diphenylimidazolidin-2-yl)ethanone
  参考文献：
  名称：

  Regioselectivity of the hydrolysis of 2-(1-alkoxyvinyl)-substituted imidazolidines, 1,3-thiazolidines, and 1,3-oxazolidines

  摘要：

  2-(1-Alkoxyvinyl)-1,3-thiazolidines reacted with H2O or D2O in the presence of 105 mol % of p-toluenesulfonic acid or trifluoroacetic acid (20 degrees C, 1 h) to give 2-acetyl-1,3-thiazolidine in quantitative yield. 2-(1-Alkoxyvinyl)-3,5-diphenylimidazolidines underwent hydrolysis in the presence of 20 mol % of an acid (20 degrees C, 24 h) at the vinyloxy group with high regioselectivity yielding 2-acetylimidazolidines. Hydrolysis of 2-(1-alkoxyvinyl)-3-phenyl-1,3-oxazolidines in the presence of 10 mol % of p-toluenesulfonic acid (20 degrees C, 5 days) takes two pathways, one of which involves the endocyclic C-O bond with ring opening and the other involves the vinyloxy group to produce 2-acetyl-3-phenyl-1,3-oxazolidine. Unlike phenyl-substituted 1,3-thiazolidines and imidazolidines, hydrolysis of their 3-methyl-and 3,5-dimethyl-substituted analogs in acid medium occurs mainly via ring opening. The observed hydrolysis pathways were interpreted in terms of B3PW91/6-311G(d,p) quantum-chemical calculations.

  DOI：

  10.1134/s1070428011120098
• 作为产物：
  描述：

  2-methoxyacrolein 、 1,4-二叠氮双环[2.2.2]辛烷 以 氯仿 为溶剂， 反应 16.0h， 以95.8%的产率得到2-(1'-methoxyvinyl)-1,3-diphenyl-1,3-imidazolidine
  参考文献：
  名称：

  Condensation of 2-alkoxypropenals with N,N- and N,O-1,2-binucleophiles. A route to 2-(1′-alkoxyvinyl)imidazo-lidines and -oxazolidines

  摘要：

  Condensation of 2-ethoxypropenal with diaminoethylene in different solvents (CHCl(3), MeCN, H(2)O, DMSO) at room temperature gives an equilibrium mixture (1:1-1.5) of tautomeric 2-(1'-ethoxyvinyl)-1,3-imidazolidine and 2-aminoethylimine of 2-ethoxypropenal as well as 1,2-bis(2'-ethoxypropenyl-ideneamino)ethylene. The latter is readily prepared in quantitative yield using a twofold excess of the aldehyde. (1)H NMR was used to demonstrate the effect of heating on the dynamics of the ring-chain tautomeric equilibrium. Reaction of the 2-alkoxypropenals with N-methyl- and N,N'-diphenyl-1,2-diaminoethylenes and with N-phenylaminoethanol gives only the corresponding substituted imidazolidines in 43-95% yield.

  DOI：

  10.1007/s10593-009-0213-y