2-(1'-ethoxyvinyl)-3-phenyl-1,3-oxazolidine | 1186100-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(1'-ethoxyvinyl)-3-phenyl-1,3-oxazolidine
• 英文别名: 2-(1-ethoxyethenyl)-3-phenyl-1,3-oxazolidine
• CAS: 1186100-71-9
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: RQZRVXDUIBTKPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1'-ethoxyvinyl)-3-phenyl-1,3-oxazolidine 在 对甲苯磺酸 作用下， 以 氯仿 、 水 为溶剂， 反应 0.08h， 以75%的产率得到1-(3-苯基-1,3-恶唑烷-2-基)乙酮
  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-乙氧基丙-2-烯醛 、 N-苯基乙醇胺 以 氯仿 为溶剂， 反应 0.07h， 以80%的产率得到2-(1'-ethoxyvinyl)-3-phenyl-1,3-oxazolidine
  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