ethyl N-chloro-N-methoxycarbamate | 745829-70-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: ethyl N-chloro-N-methoxycarbamate
• CAS: 745829-70-3
• 化学式: C₄H₈ClNO₃
• 分子量: 153.565
• InChiKey: DRSMJDSMRMFINT-UHFFFAOYSA-N

物化性质

• 沸点：
  45-46 °C(Press: 3 Torr)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  sodium benzoate 、 ethyl N-chloro-N-methoxycarbamate 以 乙腈 为溶剂， 反应 25.0h， 以60.5%的产率得到ethyl N-benzoyloxy-N-methoxycarbamate
  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-甲氧基氨基甲酸乙酯 在 次氯酸叔丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl N-chloro-N-methoxycarbamate
  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

• Geminal systems
  作者：V. G. Shtamburg、R. G. Kostyanovsky、A. V. Tsygankov、V. V. Shtamburg、O. V. Shishkin、R. I. Zubatyuk、A. V. Mazepa、S. V. Kravchenko

  DOI：10.1007/s11172-015-0822-9

  日期：2015.1

  Molecular and crystal structures of N-alkoxy-N-chloroureas and N,N-dialkoxyureas were studied together with those of N-alkoxyureas as reference compounds. N-Alkoxy-N-chloroureas were found to have an elongated N—Cl bond and a shortened N–O(Alk) bond due to the nO(Alk)→σ*N–Cl anomeric effect. Alcoholysis of N-alkoxy-N-chloro derivatives of urea, N′-arylureas, and carbamates in the presence of silver trifluoroacetate leads to sterically hindered N,N-dialkoxyureas, N,N-dialkoxy-N′-arylureas, and N,N-dialkoxycarbamates, respectively.

  研究了N-烷氧基-N-氯脲和N,N-二烷氧基脲的分子和晶体结构，同时以N-烷氧基脲作为参考化合物。发现N-烷氧基-N-氯脲具有拉长的N—Cl键和缩短的N–O(Alk)键，这归因于nO(Alk)→σ*N–Cl的异构效应。在三氟乙酸银存在下，对N-烷氧基-N-氯衍生物、N′-芳基脲和氨基甲酸酯的醇解反应分别得到空间位阻较大的N,N-二烷氧基脲、N,N-二烷氧基-N′-芳基脲和N,N-二烷氧基氨基甲酸酯。
• 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.