methyl N-chloro-N-methoxycarbamate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl N-chloro-N-methoxycarbamate
• 化学式: C₃H₆ClNO₃
• 分子量: 139.539
• InChiKey: WEOFJFXNMDTPJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium p-chlorobenzoate 、 methyl N-chloro-N-methoxycarbamate 以 乙腈 为溶剂， 反应 77.0h， 以77%的产率得到methyl N-p-chlorobenzoyloxy-N-methoxycarbamate
  参考文献：
  名称：

  Pyramidal amide nitrogen in N-acyloxy-N-alkoxyureas and N-acyloxy-N-alkoxycarbamates

  摘要：

  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.

  DOI：

  10.1070/mc2006v016n04abeh002195

文献信息

• 1-Alkoxyamino-4-dimethylaminopyridinium salts: synthesis and structure†
  作者：Vasiliy G. Shtamburg、Svetlana V. Shishkina、Victor V. Shtamburg、Alexander V. Mazepa、Gulnara K. Kadorkina、Remir G. Kostyanovsky

  DOI：10.1016/j.mencom.2016.03.030

  日期：2016.3

  N-Alkoxy-N-chlorocarbamates react with 4-dimethyl-aminopyridine yielding 1-alkoxyamino-4-dimethylamino-pyridinium chlorides, new type of O–N–N+ geminal systems. The XRD studies of two representative 1-alkoxyamino-pyridinium chlorides revealed the high pyramidal configuration of the central nitrogen atom in O–N–N+ geminal system.

  N-烷氧基-N-氯氨基甲酸酯与4-二甲基-氨基吡啶反应生成1-烷氧基氨基-4-二甲基氨基-吡啶鎓氯化物，这是新型的O–N–N +双键体系。对两种代表性的1-烷氧基氨基-吡啶鎓氯化物进行的XRD研究表明，在O–N–N +双键体系中，中心氮原子具有较高的金字塔构型。
• 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。
• Synthesis and structure of N-alkoxyhydrazines and N-alkoxy-N’,N’,N’-trialkylhydrazinium salts
  作者：Vasiliy G. Shtamburg、Oleg V. Shishkin、Roman I. Zubatyuk、Victor V. Shtamburg、Alexander V. Tsygankov、Alexander V. Mazepa、Gulnara K. Kadorkina、Remir G. Kostyanovsky

  DOI：10.1016/j.mencom.2013.09.018

  日期：2013.9

  New types of 1,1,1-trialkyl-2-alkoxyhydrazinium chlorides and N-alkoxyhydrazines were obtained by reactions of N-chloro-N-alkoxy- ureas with trimethylamine or 1,4-diaza[2.2.2]bicyclooctane and by reactions of methyl N-chloro-N-methoxycarbamate with potassium salt of N-acetylbenzenesulfonylamide. The XRD studies of N,N’-bis(methoxycarbonyl)-N,N’-dimethoxyhydrazine, N’-methoxy- N’-methoxycarbonyl-N-

  通过N-氯-N-烷氧基-脲与三甲胺或1,4-二氮杂[2.2.2]双环辛烷的反应并通过反应获得了新型的1,1,1-三烷基-2-烷氧基肼盐和N-烷氧基肼N-氯代-N-甲氧基氨基甲酸甲酯与N-乙酰基苯磺酰胺的钾盐的合成。N，N'-双（甲氧基羰基）-N，N'-二甲氧基肼，N'-甲氧基-N'-甲氧基羰基-N-乙酰基苯磺酰肼和1,1,1-三甲基-2-甲氧基肼基高氯酸盐的XRD研究显示O–N–N双键系统中中心氮原子的构型，1,1,1-三甲基-2-甲氧基肼基高氯酸盐中N–N +键的异常伸长和N–OMe键的缩短。
• 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.
• 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.