N,N’-dibenzyl-N,N’-dimethyloxalamide | 14288-21-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N’-dibenzyl-N,N’-dimethyloxalamide
• 英文别名: Oxalic acid N-benzyl-N-methyldiamide；N,N'-Dibenzyl-N,N'-dimethyloxamide
• CAS: 14288-21-2
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: CZXVNGDRTUTXRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-N-苄基氨基甲酸乙酯 在 sodium 作用下， 以 xylene 为溶剂， 反应 9.0h， 以14%的产率得到N,N’-dibenzyl-N,N’-dimethyloxalamide
  参考文献：
  名称：

  Sodium metal-promoted condensations of carbamates

  摘要：

  DOI：

  10.1021/jo00392a042

文献信息

• Visible‐Light‐Induced Palladium‐Catalyzed Dehydrogenative Carbonylation of Amines to Oxalamides
  作者：Tim Meyer、Jabor Rabeah、Angelika Brückner、Xiao‐Feng Wu

  DOI：10.1002/chem.202100009

  日期：2021.3.26

  The palladium‐catalyzed oxidative carbonylation of amines toward the synthesis of oxalamides has been established around 30 years ago and it usually needs the presence of (over)stoichiometric amounts of oxidant. In this work, the first transformation of this type in which the oxidant was replaced by visible light is described. The new approach uses a simple robust Pd complex, which can even be partially

  钯催化草胺的氧化羰基化反应已在30年前建立，通常需要化学计量（过量）的氧化剂存在。在这项工作中，描述了这种类型的第一种转化，其中氧化剂被可见光替代。新方法使用了一个简单而健壮的钯络合物，甚至可以部分回收。对照实验和EPR研究提供并支持了机理原因，表明形成了Pd I，而Pd 0是活性种。氮和中间酰基都可以被检测到。另外，通过气体GC确认了氢的形成。
• N,N-disubstituted lithium bis(carbamoyl)cuprate. A convenient complex for one-pot conversions of amines to formamides, oxamides, carbamates, and oxamic acids
  作者：Yoshiaki Wakita、Shun-Ya Noma、Minoru Maeda、Masaharu Kojima

  DOI：10.1016/0022-328x(85)80441-1

  日期：1985.12

  Lithium bis(carbamoyl)cuprates (2) were readily derived from secondary amines such as N-methylaniline, N-methylbenzylamine, and diethylamine, under mild carbonylation conditions (0°C, 1 atm of carbon monoxide), but diphenylamine and benzylphenylamine were unsuitable as the starting materials. The carbamoylcopper complexes 2 formed in ether were readily converted to the corresponding formamides, oxamides

  在轻度羰基化条件下（0°C，1 atm一氧化碳），双（氨基甲酰基）锂锂（2）很容易衍生自仲胺，例如N-甲基苯胺，N-甲基苄胺和二乙胺，但二苯胺和苄基苯胺不适合作为起始材料。通过适当的处理，在醚中形成的氨基甲酰铜络合物2易于转化为相应的甲酰胺，草酰胺，氨基甲酸酯和草酰胺酸。的形成和稳定性2很大程度上取决于所使用的溶剂。溶剂（DME，THF和HMPA）的较高极性作用使2的稳定性降低，并导致在进一步反应中伴随释放出一氧化碳。发现钯催化剂对于2与碘苯或（E）-β-溴苯乙烯的交叉偶联反应是有效的。
• Reactivity of Carbamoyl Radicals. A New, General, Convenient Free-Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid
  作者：Francesco Minisci、Francesca Fontana、Fausta Coppa、Yong Ming Yan

  DOI：10.1021/jo00122a020

  日期：1995.9

  A new, general, simple synthesis of isocyanates was developed by oxidation of monoamides of oxalic acid with peroxydisulfate catalyzed by Ag and Cu salts. The reaction was carried out in a two-phase system (water and an organic solvent), and it is suitable also for practical applications, due to the simple experimental conditions and the inexpensive as well as nontoxic reagents. The first example of homolytic intramolecular aromatic carbamoylation is also reported.
• CRUMRINE, D. S.;DIESCHBOURG, T. A.;OTOOLE, J. G.;TASSONE, B. A.;VANDEBURG+, J. ORG. CHEM., 52,(1987) N 16, 3699-3701
  作者：CRUMRINE, D. S.、DIESCHBOURG, T. A.、OTOOLE, J. G.、TASSONE, B. A.、VANDEBURG+

  DOI：——

  日期：——
• Sodium metal-promoted condensations of carbamates
  作者：David S. Crumrine、Thomas A. Dieschbourg、James G. O'Toole、Benjamin A. Tassone、Suzanne C. Vandeburg

  DOI：10.1021/jo00392a042

  日期：1987.8