1-<2-(Methylamino)ethyl>-3-butyl-1-methylurea

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 1-<2-(Methylamino)ethyl>-3-butyl-1-methylurea
• 英文别名: 3-Butyl-1-methyl-1-[2-(methylamino)ethyl]urea
• 化学式: C₉H₂₁N₃O
• 分子量: 187.285
• InChiKey: YAOBMUFNVBWPSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二氧化碳 、 正丁胺 、 N,N'-二甲基乙二胺 在 tetraphosphorus decasulfide 、 三苯基氧化锑 作用下， 以 苯 为溶剂， 80.0 ℃ 、4.9 MPa 条件下， 以10%的产率得到1,3-二甲基-2-咪唑啉酮
  参考文献：
  名称：

  Carbonylation of amines by carbon dioxide in the presence of an organoantimony catalyst

  摘要：

  1,3-Dialkylureas (RNHCONHR, where R = Bu, i-Bu, s-Bu, t-Bu, allyl, Ph) and tetramethylurea were successfully prepared at 80-degrees-C under an initial CO2 pressure of 4.9 MPa, from the corresponding amines and carbon dioxide with catalysis by triphenylstibine oxide and assistance from tetraphosphorus decasulfide (Ph3SbO/P4S10). Monitoring of the reaction by C-13 NMR revealed that the successive thiolation of carbamic acid to an intermediate antimony carbamate species and aminolysis of the carbamothioic acid thus formed constitute the reaction course. Cyclic ureas can also be synthesized by similar carbonylations of diamines (RNHCH2CH2NHR'; where R, R' = H, H; Me, H; Ph, H; HOCH2CH2, H; HOCHMeCH2, H; Me, Me). Furthermore, the Ph3SbO/P4S10 catalyst system enabled the preparation of trisubstituted ureas such as 1-butyl-3,3-diethylurea by a selective cocarbonylation of butylamine and diethylamine.

  DOI：

  10.1021/jo00052a060

文献信息

• Carbonylation of amines by carbon dioxide in the presence of an organoantimony catalyst
  作者：Ryoki Nomura、Yasuhiro Hasegawa、Mikio Ishimoto、Takayuki Toyosaki、Haruo Matsuda

  DOI：10.1021/jo00052a060

  日期：1992.12

  1,3-Dialkylureas (RNHCONHR, where R = Bu, i-Bu, s-Bu, t-Bu, allyl, Ph) and tetramethylurea were successfully prepared at 80-degrees-C under an initial CO2 pressure of 4.9 MPa, from the corresponding amines and carbon dioxide with catalysis by triphenylstibine oxide and assistance from tetraphosphorus decasulfide (Ph3SbO/P4S10). Monitoring of the reaction by C-13 NMR revealed that the successive thiolation of carbamic acid to an intermediate antimony carbamate species and aminolysis of the carbamothioic acid thus formed constitute the reaction course. Cyclic ureas can also be synthesized by similar carbonylations of diamines (RNHCH2CH2NHR'; where R, R' = H, H; Me, H; Ph, H; HOCH2CH2, H; HOCHMeCH2, H; Me, Me). Furthermore, the Ph3SbO/P4S10 catalyst system enabled the preparation of trisubstituted ureas such as 1-butyl-3,3-diethylurea by a selective cocarbonylation of butylamine and diethylamine.