N-chloro-N-butyloxyurea | 502448-02-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: N-chloro-N-butyloxyurea
• 英文别名: N-n-butoxy-N-chlorourea；N-n-butyloxy-N-chlorourea；1-butoxy-1-chlorourea
• CAS: 502448-02-4
• 化学式: C₅H₁₁ClN₂O₂
• 分子量: 166.608
• InChiKey: XQEJHYCLBTVLRV-UHFFFAOYSA-N

物化性质

• 熔点：
  24-26 °C (decomp)
• 沸点：
  214.0±23.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.56
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-chloro-N-butyloxyurea 以 乙腈 为溶剂， 反应 55.0h， 生成 N-n-butoxy-N-methoxyurea
  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
• 作为产物：
  描述：

  N-n-butoxyurea 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-butyloxyurea
  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。
• Acyloxy group exchange in N-acyloxy-N-alkoxyamides
  作者：Vasiliy G. Shtamburg、Alexandr V. Tsygankov、Evgeniy A. Klots、Remir G. Kostyanovsky

  DOI：10.1070/mc2004v014n05abeh001908

  日期：2004.1

  Acyloxy group exchange at the nitrogen atom proceeds in the interaction of N-acyloxy-N-alkoxyureas, N-acyloxy-N-alkoxybenzamides and N-acyloxy-N-alkoxycarbamates with Na and K carboxylates in MeCN.