N,N'-bis-carbomethoxyethylenediamine | 6268-31-1

• 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'-bis-carbomethoxyethylenediamine
• 英文别名: N,N'-ethanediyl-bis-carbamic acid dimethyl ester；N,N'-Aethandiyl-bis-carbamidsaeure-dimethylester；N,N'-Di(acetoxycarbonyl)ethylendiamin；N.N'-Ethylen-bis-(O-methylurethan)；Dimethyl ethane-1,2-diylbiscarbamate；methyl N-[2-(methoxycarbonylamino)ethyl]carbamate
• CAS: 6268-31-1
• 化学式: C₆H₁₂N₂O₄
• mdl: MFCD00484114
• 分子量: 176.172
• InChiKey: OCUKKHVJDGNKNX-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C(Solv: benzene (71-43-2))
• 沸点：
  325.6±25.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis-carbomethoxyethylenediamine 在 盐酸 、 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 69.0h， 生成 N,N'-Dicarbomethoxy-N,N'-bis(mercaptomethyl)ethylenediamine
  参考文献：
  名称：

  Synthesis of dithiols as reducing agents for disulfides in neutral aqueous solution and comparison of reduction potentials

  摘要：

  Several dithiols have been prepared that are useful for the reduction of disulfides in aqueous solution. The reduction potential of these dithiols have been determined from the measurement of the equilibrium constant of thiol/disulfide interchange with oxidized dithiothreitol using a H-1 NMR assay. The values of pK(a) of some of the dithiols were measured to estimate their rate of reduction of disulfides. Bis(2-mercaptoethyl) sulfone (2), N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine (5), and meso-2,5-dimercapto-N,N,N',N'-tetramethyladipamide (6) are especially interesting as alternatives to dithiothreitol for the reduction of disulfides.

  DOI：

  10.1021/jo00055a015
• 作为产物：
  描述：

  1-methoxycarbonyl-2-imidazolidinone 生成 N,N'-bis-carbomethoxyethylenediamine
  参考文献：
  名称：

  MATSUMURA NOBORU; YAGYU YOSHIO; KAWAI HIROSKI; OSUJI YOSHIO; IMOTO EIJI, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI, J. CHEM. SOS. JAR., CHEM. AND I+

  摘要：

  DOI：

文献信息

• Methoxycarbonylation of Aliphatic Diamines with Dimethyl Carbonate Promoted by<i>in situ</i>Generated Hydroxide Ion: A Mechanistic Consideration
  作者：Dae Won Kim、Eun Soo Huh、Sang Do Park、Ly Vinh Nguyen、Mai Dao Nguyen、Hoon Sik Kim、Minserk Cheong、Dinh Quan Nguyen

  DOI：10.1002/adsc.200900699

  日期：2010.2.15

  The methoxycarbonylation reactions of aliphatic diamines with dimethyl carbonate are accelerated greatly in the presence of water. Theoretical investigations on the mechanistic aspects of the methoxycarbonylation of 1,6-hexanediamine strongly suggest that the hydroxide ion, generated in situ from the interaction of 1,6-hexanediamine with water, is an active catalytic species and plays a pivotal role

  在水的存在下，脂肪族二胺与碳酸二甲酯的甲氧基羰基化反应大大加快。对1,6-己二胺甲氧基羰基化机理的理论研究有力地表明，由1,6-己二胺与水的相互作用原位产生的氢氧根离子是一种活性的催化物质，在速率上起关键作用。 -确定从氨基提取氢的步骤。
• Synthesis of Ketene <i>N</i>,<i>N</i>-Acetals by Copper-Catalyzed Double-Amidation of 1,1-Dibromo-1-alkenes
  作者：Alexis Coste、François Couty、Gwilherm Evano

  DOI：10.1021/ol901831s

  日期：2009.10.1

  efficient procedure for the preparation of ketene N,N-acetals by copper-catalyzed double amidation of 1,1-dibromo-1-alkenes is reported. The reaction was found to be general, and ketene aminals could be obtained in good yields when potassium phosphate in toluene was used at 80 °C. The reaction was found to proceed through a regioselective monocoupling reaction followed by dehydrobromination and hydroamidation

  报道了通过铜催化的1，1-二溴-1-烯烃双酰胺化反应制备烯酮N，N-乙缩醛的有效方法。发现该反应是一般的，并且当在80℃下使用甲苯中的磷酸钾时，可以以良好的产率获得乙烯酮缩醛。发现该反应通过区域选择性单偶联反应进行，然后进行脱氢溴化和加氢酰胺化。
• Nonisocyanate route to 2,5‐bis(hydroxymethyl)furan‐based polyurethanes crosslinked by reversible diels–alder reactions
  作者：Lu Zhang、Frederick C. Michel、Anne C. Co

  DOI：10.1002/pola.29418

  日期：2019.7.15

  5‐bis(hydroxymethyl)furan in combination with 1,4‐butanediol through transurethanization reactions with dicarbamates. This was followed by detailed characterization to study their properties. The furan functional groups of these NIPUs made it possible to form thermally reversible crosslinks with a bismaleimide through Diels‐Alder reactions, and the reversibly crosslinked NIPU materials showed great potential

  通过与二氨基甲酸酯进行氨基甲酸酯化反应，使用2,5-双（羟甲基）呋喃与1,4-丁二醇合成了一系列非异氰酸酯聚氨酯（NIPU）。然后进行详细的表征以研究其性能。这些NIPU的呋喃官能团使得通过Diels-Alder反应与双马来酰亚胺形成热可逆交联成为可能，而可逆交联的NIPU材料则具有开发具有可回收和自愈特性的生物基PU产品的巨大潜力。
• Effective synthesis of dimethylhexane-1,6-dicarbamate from 1,6-hexanediamine and dimethyl carbonate using 3-amino-1,2,4-triazole potassium as a solid base catalyst at ambient temperature
  作者：Peixue Wang、Yuqing Fei、Qinghe Li、Youquan Deng

  DOI：10.1039/c6gc02509a

  日期：——

  A newly basic catalyst 3-Amino-1,2,4-triazole potassium (KATriz) was prepared, characterized and employed for synthesis of dimethylhexane 1,6-dicarbamate (MHDC) by methoxycarbonylation of 1,6-hexanediamine (HDA) and dimethyl carbonate (DMC). Results showed that...

  制备了新型碱性催化剂3-氨基-1,2,4-三唑钾（KATriz），表征并用于通过1,6-己二胺（HDA）和二甲基的甲氧基羰基化合成二甲基己烷1,6-二氨基甲酸酯（MHDC）碳酸盐（DMC）。结果表明...
• METHOD FOR PREPARING ALIPHATIC DIISOCYANATE
  申请人：UNIVERSITY-INDUSTRY COOPERATION GROUP OF KYUNG HEE UNIVERSITY

  公开号：US20140303399A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for preparing an aliphatic diisocyanate by pyrolyzing an aliphatic dicarbamate in liquid phase, using a tin (II) or (IV) compound as a catalyst and a zwitterionic compound as a stabilizer, thereby remarkably inhibiting high-boiling by-products and providing the aliphatic diisocyanate with high yield.

  本发明涉及一种通过在液相中热解脂肪族二碳酸酯，使用锡（II）或（IV）化合物作为催化剂和带电离子化合物作为稳定剂的方法来制备脂肪族二异氰酸酯，从而显著抑制高沸点副产物，并提供高产率的脂肪族二异氰酸酯。