N-chloro-N-ethoxyurea | 745829-65-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-chloro-N-ethoxyurea
• 英文别名: 1-chloro-1-ethoxyurea
• CAS: 745829-65-6
• 化学式: C₃H₇ClN₂O₂
• 分子量: 138.554
• InChiKey: ZCSUWXVMSMHKER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吡啶 、 N-chloro-N-ethoxyurea 以 乙醚 为溶剂， 以73%的产率得到N-nethoxy-N-(1-pyridinium)urea chloride
  参考文献：
  名称：

  Synthesis, structure and properties of N-alkoxy-N-(1-pyridinium)urea salts, N-alkoxy-N-acyloxyureas and N,N-dialkoxyureas

  摘要：

  N-Alkoxy-N-(1-pyridinium)urea salts 3, 4 have been prepared, the conversions of N-acetoxy-N-methoxyurea 7 into N,N '-di-methoxyurea 8 and of N-n-propyloxy-N-(1-pyridinium)-N ',N '-dimethylurea chloride 6 into N,N-dimethoxy-N ',N '-dimethylurea 11 were carried out. A high pyramidality of the amide nitrogen in O-N-X groups [X = N+C5H5, OMe, OC(o)C6H4Cl-p] has been revealed by XRD studies of ureas 3b, 8 and N-p-chlorobenzoyloxy-N-n-butyloxyurea 9.

  DOI：

  10.1016/j.mencom.2007.05.016
• 作为产物：
  描述：

  N-ethoxy-urea 在 次氯酸叔丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到N-chloro-N-ethoxyurea
  参考文献：
  名称：

  Geminal systems. 50. Synthesis and alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides

  摘要：

  Procedures were developed for the synthesis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides by the reactions of the corresponding N-alkoxy-N-chloro derivatives with sodium carboxylates in MeCN. N-Chloro-N-etlioxy-p-toluenesulfonamide was inert in this reaction. Alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and tert-alkylamines afforded the corresponding N,N-dialkoxy derivatives, whereas alcoholysis of N-acetoxy-N-ethoxybenzamide gave rise to alkyl benzoates.

  DOI：

  10.1023/b:rucb.0000011887.40529.b0

文献信息

• Nucleophilic substitution at nitrogen atom. N-Alkoxy-N-(dimethoxyphosphoryl)ureas, synthesis and structure
  作者：Vasiliy G. Shtamburg、Evgeniy A. Klots、Victor V. Shtamburg、Andrey A. Anishchenko、Svitlana V. Shishkina、Alexander V. Mazepa

  DOI：10.1016/j.molstruc.2022.134865

  日期：2023.4

  N-Alkoxy-N-chloroureas react with trimethyl phosphite in ether forming N-alkoxy-N-(dimethoxyphosphory)ureas. The obtained N-alkoxy-N-(dimethoxyphosphoryl)ureas are the products of the nucleophilic substitution at nitrogen. This reaction is a completely new way to receive the N-phosphorylureas synthetically. By this research the possibility of the N–P bond formation by N-alkoxy-N-chloroureas interaction with P-nucleophiles

  N-烷氧基-N-氯脲与亚磷酸三甲酯在醚中反应形成N-烷氧基-N- (二甲氧基磷酸)脲。得到的N-烷氧基-N- (二甲氧基磷酰基)脲是氮原子上亲核取代的产物。该反应是一种全新的合成得到N-磷酸脲的方法。通过这项研究，证明了 N-烷氧基-N-氯脲与P-亲核试剂相互作用形成 N-P 键的可能性。N -烷氧基- N -(二甲氧基磷酸)脲的结构已由1H、31 P和13 C NMR光谱、质谱和XRD研究。N-甲氧基-N- (二甲氧基磷酸)脲和Nn-丁氧基-N- (二甲氧基磷酸)脲的XRD研究证明了它们独特的结构特征。在这些化合物中，两个氮原子都具有平面构型。氨基甲酰基和 N-O 键位于平面内。因此，已经发现N-烷氧基-N- (二甲氧基磷酰基)脲具有许多不同于异头脲的结构特征。
• Pyramidal amide nitrogen in N-acyloxy-N-alkoxyureas and N-acyloxy-N-alkoxycarbamates
  作者：Oleg V. Shishkin、Roman I. Zubatyuk、Vasiliy G. Shtamburg、Alexander V. Tsygankov、Evgeny A. Klots、Alexander V. Mazepa、Remir G. Kostyanovsky

  DOI：10.1070/mc2006v016n04abeh002195

  日期：2006.1

  The XRD studies of N-acyloxy-N-alkoxyamides 1, 2 have revealed a highly pyramidal configuration of amide nitrogen in the O-N-O group.
• Geminal systems. 50. Synthesis and alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides
  作者：V. G. Shtamburg、E. A. Klots、A. P. Pleshkova、V. I. Avramenko、S. P. Ivonin、A. V. Tsygankov、R. G. Kostyanovsky

  DOI：10.1023/b:rucb.0000011887.40529.b0

  日期：2003.10

  Procedures were developed for the synthesis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides by the reactions of the corresponding N-alkoxy-N-chloro derivatives with sodium carboxylates in MeCN. N-Chloro-N-etlioxy-p-toluenesulfonamide was inert in this reaction. Alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and tert-alkylamines afforded the corresponding N,N-dialkoxy derivatives, whereas alcoholysis of N-acetoxy-N-ethoxybenzamide gave rise to alkyl benzoates.
• Synthesis, structure and properties of N-alkoxy-N-(1-pyridinium)urea salts, N-alkoxy-N-acyloxyureas and N,N-dialkoxyureas
  作者：Vasiliy G. Shtamburg、Oleg V. Shishkin、Roman I. Zubatyuk、Svetlana V. Kravchenko、Alexander V. Tsygankov、Victor V. Shtamburg、Vitaliy B. Distanov、Remir G. Kostyanovsky

  DOI：10.1016/j.mencom.2007.05.016

  日期：2007.5

  N-Alkoxy-N-(1-pyridinium)urea salts 3, 4 have been prepared, the conversions of N-acetoxy-N-methoxyurea 7 into N,N '-di-methoxyurea 8 and of N-n-propyloxy-N-(1-pyridinium)-N ',N '-dimethylurea chloride 6 into N,N-dimethoxy-N ',N '-dimethylurea 11 were carried out. A high pyramidality of the amide nitrogen in O-N-X groups [X = N+C5H5, OMe, OC(o)C6H4Cl-p] has been revealed by XRD studies of ureas 3b, 8 and N-p-chlorobenzoyloxy-N-n-butyloxyurea 9.