methyl N-[(4-methoxyphenyl)carbamoylamino]carbamate | 223401-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-[(4-methoxyphenyl)carbamoylamino]carbamate
• CAS: 223401-26-1
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: BKJWKBLENOYCPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-[(4-methoxyphenyl)carbamoylamino]carbamate 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以78%的产率得到1,2,4-三氮杂茂-3,5-二酮,4-(4-甲氧苯基)-
  参考文献：
  名称：

  通过乌拉唑的 N-N 键断裂和分子内环化合成不对称二氢三嗪-2,4-二酮

  摘要：

  一种新的不对称二氢三嗪-2,4-二酮合成方法已通过碱诱导的乌拉唑衍生物断裂，然后进行分子内环化的策略完成。用 LDA 处理取代的 urazole 衍生物会导致 N-N 键断裂，产生亚胺，亚胺以分子内的方式被捕获，从而得到具有良好至优异产率的产品。这种转变的特点包括原子经济性和对芳基取代基的广泛耐受性。当使用不同取代的urazole衍生物时，仅获得一种二氢三嗪-2，4-二酮异构体。我们还展示了将这种二氢三嗪-2,4-二酮转化为三嗪-2,4-二酮和三嗪-2,4,6-三酮，扩大了这种方法的范围。

  DOI：

  10.1016/j.tetlet.2022.154076
• 作为产物：
  描述：

  甲氧苯胺 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.5h， 生成 methyl N-[(4-methoxyphenyl)carbamoylamino]carbamate
  参考文献：
  名称：

  通过乌拉唑的 N-N 键断裂和分子内环化合成不对称二氢三嗪-2,4-二酮

  摘要：

  一种新的不对称二氢三嗪-2,4-二酮合成方法已通过碱诱导的乌拉唑衍生物断裂，然后进行分子内环化的策略完成。用 LDA 处理取代的 urazole 衍生物会导致 N-N 键断裂，产生亚胺，亚胺以分子内的方式被捕获，从而得到具有良好至优异产率的产品。这种转变的特点包括原子经济性和对芳基取代基的广泛耐受性。当使用不同取代的urazole衍生物时，仅获得一种二氢三嗪-2，4-二酮异构体。我们还展示了将这种二氢三嗪-2,4-二酮转化为三嗪-2,4-二酮和三嗪-2,4,6-三酮，扩大了这种方法的范围。

  DOI：

  10.1016/j.tetlet.2022.154076

文献信息

• ZrCl₄-Mediated Regioselective Electrophilic Amination of Activated Arenes with New Alkyl Arylaminocarbonyldiazenecarboxylates:  Intermolecular and Intramolecular Reactions
  作者：Roman Lenaršič、Marijan Kočevar、Slovenko Polanc

  DOI：10.1021/jo9821170

  日期：1999.4.1
• Proton-transfer chemistry of urazoles and related imides, amides, and diacyl hydrazides
  作者：M. J. Bausch、B. David、P. Dobrowolski、C. Guadalupe-Fasano、R. Gostowski、D. Selmarten、V. Prasad、A. Vaughn、L. H. Wang

  DOI：10.1021/jo00019a034

  日期：1991.9

  Equilibrium acidity constants have been determined for 1,2,4-triazolidine-3,5-dione (urazole), several substituted urazoles, and other related acids, in both dimethyl sulfoxide (DMSO) and aqueous solution. In DMSO, urazole has a pK(a) of 13.1. In water, urazole has a pK(a) of 5.8. In general, N-methyl and N-phenyl substituents are found to acidify the urazole moiety, in both DMSO and water. The acidifying effects of these substituents are attenuated by a factor of 3.3 in water. The solvent effects are ascribed to the aqueous stabilization of urazole anions via hydrogen-bonding interactions and the aqueous-promoted relief of lone pair-lone pair electronic interactions that manifest themselves upon deprotonation of a hydrazyl proton in 1 and related species. That a hydrazyl proton in 1 is at least as acidic as the imide proton in 1 is comparison of C-13 NMR spectra for the urazoles and related nitrogen acids with C-13 spectra for the conjugate bases derived from these species. Upon loss of an imide proton, in both DMSO-d6 and D2O solutions, carbonyl carbon atoms present in succinimide as well as appropriately substituted urazoles and hydantoins experience substantial (13-17 ppm) downfield shifts. In contrast, deprotonation of 4-substituted and 1,4-substituted urazoles, 4,4-dimethylpyrazolidine-3,5-dione, and diacetylhydrazine (species that contain hydrazyl acidic protons) results in shifts in the positions of the carbonyl resonances that range from 5 ppm upfield to 3 ppm downfield. Deprotonation of species containing both imide and hydrazyl protons (i.e., urazole and 1-substituted urazoles) results in shifts in the carbonyl carbon resonances consistent with hydrazyl proton removal. Comparison of DMSO-phase pK(a)'s for acetamide (25.5), diacetylhydrazine (16.7), 4,4-dimethylpyrazolidine-3,5-dione (13.5), and urazole (13.5), and urazole (13.1) suggest that the remarkable acidity of the hydrazyl proton in urazole and substituted urazoles is due mainly to its cyclic diacyl hydrazide structure.
• Synthesis of unsymmetrical dihydro triazine-2,4-diones by the N–N bond fragmentation of urazoles followed by intramolecular cyclization
  作者：Subhaskar R. Panga、Roger G. Hall、Rashmi V. Samant、Mark Montgomery、Ashok S. Shyadligeri

  DOI：10.1016/j.tetlet.2022.154076

  日期：2022.9

  A new synthesis of unsymmetrical dihydro triazine-2,4- diones has been accomplished, through the strategy of a base-induced fragmentation of urazole derivatives, followed by an intramolecular cyclisation. Treating substituted urazole derivatives with LDA resulted in fragmentation of the N–N bond generating an imine, which was trapped in an intramolecular fashion to give products in good to excellent

  一种新的不对称二氢三嗪-2,4-二酮合成方法已通过碱诱导的乌拉唑衍生物断裂，然后进行分子内环化的策略完成。用 LDA 处理取代的 urazole 衍生物会导致 N-N 键断裂，产生亚胺，亚胺以分子内的方式被捕获，从而得到具有良好至优异产率的产品。这种转变的特点包括原子经济性和对芳基取代基的广泛耐受性。当使用不同取代的urazole衍生物时，仅获得一种二氢三嗪-2，4-二酮异构体。我们还展示了将这种二氢三嗪-2,4-二酮转化为三嗪-2,4-二酮和三嗪-2,4,6-三酮，扩大了这种方法的范围。