<2-(13)C>-1-ethyl-3-(3-(dimethylamino)propyl)thiourea | 141727-01-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫脲类
• 英文名称: <2-(13)C>-1-ethyl-3-(3-(dimethylamino)propyl)thiourea
• CAS: 141727-01-7
• 化学式: C₈H₁₉N₃S
• 分子量: 190.314
• InChiKey: PFUBBBJVHVTSPB-VJJZLTLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.3
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  <2-(13)C>-1-ethyl-3-(3-(dimethylamino)propyl)thiourea 在 mercury(II) oxide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 <2-(13)C>-1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide
  参考文献：
  名称：

  Solid-state NMR of N-acylureas derived from the reaction of hyaluronic acid with isotopically-labeled carbodiimides

  摘要：

  Hyaluronic acid (HA) is a naturally-occurring linear polysaccharide consisting of alternating D-glucuronic acid and N-acetyl-D-glucosamine residues. Reaction of the carboxyl group of the glucuronate residues with 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDC) in the presence of primary amines yielded only the N-acylurea adducts rather than the expected amide coupling products. To determine the nature of this linkage unambiguously and to deduce the primary structure of the N-acylurea products, C-13- and N-15-labeled 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide were synthesized. The isotopically-labeled carbodiimides were coupled to the carboxyl group of HA (molecular size ca. 2 000 000 Da) in water at pH = 4.75. The modified polysaccharides were then isolated, purified, and examined by cross polarization and magic angle spinning (CP-MAS) solid-state C-13 and N-15 NMR. The chemical shifts and states of protonation of the nitrogens confirmed the presence of two isomeric N-acylureas in unequal amounts and ruled out the presence of any unrearranged O-acylurea product.

  DOI：

  10.1021/ja00041a010
• 作为产物：
  描述：

  <(13)C>ethyl isothiocyanate 、 N,N-二甲基-1,3-二氨基丙烷 以 氯仿 为溶剂， 生成 <2-(13)C>-1-ethyl-3-(3-(dimethylamino)propyl)thiourea
  参考文献：
  名称：

  Solid-state NMR of N-acylureas derived from the reaction of hyaluronic acid with isotopically-labeled carbodiimides

  摘要：

  Hyaluronic acid (HA) is a naturally-occurring linear polysaccharide consisting of alternating D-glucuronic acid and N-acetyl-D-glucosamine residues. Reaction of the carboxyl group of the glucuronate residues with 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDC) in the presence of primary amines yielded only the N-acylurea adducts rather than the expected amide coupling products. To determine the nature of this linkage unambiguously and to deduce the primary structure of the N-acylurea products, C-13- and N-15-labeled 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide were synthesized. The isotopically-labeled carbodiimides were coupled to the carboxyl group of HA (molecular size ca. 2 000 000 Da) in water at pH = 4.75. The modified polysaccharides were then isolated, purified, and examined by cross polarization and magic angle spinning (CP-MAS) solid-state C-13 and N-15 NMR. The chemical shifts and states of protonation of the nitrogens confirmed the presence of two isomeric N-acylureas in unequal amounts and ruled out the presence of any unrearranged O-acylurea product.

  DOI：

  10.1021/ja00041a010