N-氨基甲酰氨基甲酸甲酯 | 761-89-7

• 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
• 中文名称: N-氨基甲酰氨基甲酸甲酯
• 英文名称: allophanic acid methyl ester
• 英文别名: methyl allophanate；methoxycarbonyl urea；methyl N-carbamoylcarbamate
• CAS: 761-89-7
• 化学式: C₃H₆N₂O₃
• mdl: MFCD00047869
• 分子量: 118.092
• InChiKey: ICYIIEFSHYSYRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-氨基甲酰氨基甲酸甲酯 在 水 、 一水合肼 作用下， 生成 尿唑
  参考文献：
  名称：

  HYDRAZINE DERIVATIVES OF THE CARBONIC AND THIOCARBONIC ACIDS. VI. A NEW SYNTHESIS OF URAZOLE¹

  摘要：

  DOI：

  10.1021/jo01123a007
• 作为产物：
  描述：

  氨基甲酸甲酯 在 磷酸酐 作用下， 生成 N-氨基甲酰氨基甲酸甲酯
  参考文献：
  名称：

  Biilmann; Bjerrum, Chemische Berichte, 1917, vol. 50, p. 506

  摘要：

  DOI：

文献信息

• Studies on Organic Sulfur Compounds. XIII. The Oxidation Reaction of Alkoxycarbonylthioureas with Bromine
  作者：MITSUO NAGANO、MICHIKO OSHIGE、TAKASHI MATSUI、JUNZO TOBITSUKA、KOZO OYAMADA

  DOI：10.1248/cpb.21.2396

  日期：——

  N-Alkoxycarbonylthioureas (A) were reacted with bromine in CHCl3 to afford sulfur, alkoxycarbonylureas (B), 3, 5-bis (alkoxycarbonylimino)-1, 2, 4-dithiazolidines (C), 3, 5-bis-(alkoxycarbonylamino)-1, 2, 4-thiadiazoles (D), 2-alkoxycarbonyl-5-alkoxycarbonylamino-3-imino-1, 2, 4-thiadiazolines (E) and 3-amino-5-alkoxycarbonylamino-1, 2, 4-thiadiazoles (F). This paper describes in detail on the confirmation of the structures of these reaction products.

  N-烷氧基羰基硫脲（A）与溴在氯仿中反应，生成硫、烷氧基羰基脲（B）、3, 5-双（烷氧基羰基亚氨基）-1, 2, 4-二硫杂戊烷（C）、3, 5-双（烷氧基羰基氨基）-1, 2, 4-噻二唑（D）、2-烷氧基羰基-5-烷氧基羰基氨基-3-亚氨基-1, 2, 4-噻二唑啉（E）和3-氨基-5-烷氧基羰基氨基-1, 2, 4-噻二唑（F）。本文详细描述了这些反应产物结构的确认。
• Therapeutic Methods Used for Otolaryngological Problems during the Byzantine Period
  作者：Ioanna A. Ramoutsaki、Ioannis A. Ramoutsakis、Chariton E. Papadakis、Emmanuel S. Helidonis

  DOI：10.1177/000348940211100612

  日期：2002.6

  Evidence of herbal, animal, and chemical substances from the natural world used in medicines for otolaryngological problems, including opium, hyoscyamus, barley, honey, dried beans and peas, olives, fruits, Agaricus, castoreum, cassia, and afronitron, was traced in the Byzantine medical treatises, mainly from the 4th century ad to the 15th century ad. The texts of Antyllus, Orivasios of Pergamos, Aetios of Amida, Alexander of Tralles, Paul Aeginitis, Leon Iatrosophistis, Theophanis Nonnos, Nickolaos Myrepsos, Michael Psellos, and others strongly suggest the influence of ancient Greek and Roman medicine, but at the same time stress original medical thought. The main otolaryngological problems encountered in that period were loss of hearing, purulent otitis, rupture of the tympanic membrane, pharyngitis, laryngitis, rhinitis, acute tonsillitis, seasickness, vertigo, fracture of the nose, and cancers of the ear, larynx, nose, and oral cavity. The tradition stating that remedies were the final products of substance combinations, started in the classical period (5th and 4th centuries bc), is presented clearly and in detail in Byzantine prescriptions related to otolaryngology.

  拜占庭医学著作中追溯到自然界中使用于耳鼻喉问题的草药、动物和化学物质的证据，包括鸦片、颠茄、大麦、蜂蜜、干豆和豌豆、橄榄、水果、琥珀菇、海狸香、肉桂和非洲沉香，主要出现在公元4世纪到15世纪期间。安蒂卢斯、佩尔加莫斯的奥里瓦西奥斯、阿米达的艾提奥斯、特拉勒斯的亚历山大、保罗·阿吉尼蒂斯、利昂·医学家、费南尼斯·诺诺斯、尼古拉斯·米雷普索斯、迈克尔·普塞洛斯等人的文本强烈表明了古希腊和罗马医学的影响，但同时强调了原创的医学思想。当时主要的耳鼻喉问题包括听力丧失、化脓性中耳炎、鼓膜破裂、咽炎、喉炎、鼻炎、急性扁桃体炎、晕船、眩晕、鼻骨骨折以及耳、喉、鼻和口腔癌症。在拜占庭耳鼻喉学处方中，明确详细地呈现了古典时期（公元前5世纪和4世纪）药物是物质组合的最终产品的传统。
• Revealing CSA Tensors and Hydrogen Bonding in Methoxycarbonyl Urea: A combined ¹³C, ¹⁵N and ¹³C¹⁴N₂ Dipolar Chemical Shift NMR and DFT Study
  作者：Sven Macholl、Frank Börner、Gerd Buntkowsky

  DOI：10.1524/zpch.217.12.1473.20470

  日期：2003.12.1

  Methoxycarbonyl urea (MCU), a potential long-term nitrogen fertilizer, is studied by ¹³C and ¹⁵N dipolar chemical shift NMR spectroscopy and ab initio calculations. Employing a combination of dipolar chemical shift NMR, selective isotope labeling and ab initio gas phase calculations, possible molecular structures and chemical shielding tensors of all ¹⁵N nuclei and of two out of the three ¹³C nuclei were revealed. Four possible stable configurations of the molecule with different energies were found in the calculations. The CSA tensors were calculated for these configurations. While the calculated ¹³C(urea) CSA tensor orientation of the configuration with the lowest energy is in good agreement with the experimental tensor orientation, there are pronounced differences between calculated and experimental tensor eigenvalues. These differences are a clear indication of the presence of intermolecular hydrogen bonds in the experimental sample, which are neglected in the gas phase calculations. Four different possible orientations of the experimental ¹³C(urea) CSA tensor exist, due to symmetry. This ambiguity is solved by comparison with results from GIAO calculations of the ¹³C CSA tensor, employing the minimum energy configuration (EEZ). It is found that the orientation, where δ₁₁ points approximately in direction of N(imide), δ₂₂ approximately in direction of the C=O bond, and δ₃₃ is oriented perpendicular to the molecular frame, is adopted in the molecule.

  甲氧基羰基脲（MCU）是一种潜在的长效氮肥，通过¹³C和¹⁵N偶极化化学位移核磁共振光谱和ab initio计算进行了研究。采用偶极化化学位移核磁共振、选择性同位素标记和ab initio气相计算的组合，揭示了所有¹⁵N核和三个¹³C核中两个的可能分子结构和化学屏蔽张量。计算中发现了四种可能的稳定构型，具有不同的能量。对于这些构型，计算了化学位移张量。虽然具有最低能量的构型的计算的¹³C（脲）化学位移张量方向与实验张量方向吻合良好，但计算和实验张量特征值之间存在显著差异。这些差异明确表明了实验样品中存在的分子间氢键的存在，这在气相计算中被忽略了。实验¹³C（脲）化学位移张量存在四种不同的可能方向，由于对称性而产生的。通过与¹³C化学位移张量的GIAO计算结果进行比较，采用最小能量构型（EEZ），解决了这种歧义。发现在分子中采用了δ₁₁大致指向N（imide）方向，δ₂₂大致指向C=O键方向，δ₃₃与分子框架垂直的方向。

• Biltz; Jeltsch, Chemische Berichte, 1923, vol. 56, p. 1918
  作者：Biltz、Jeltsch

  DOI：——

  日期：——
• Bussas, Reinhard; Kresze, Guenter, Liebigs Annalen der Chemie, 1982, # 3, p. 545 - 563
  作者：Bussas, Reinhard、Kresze, Guenter

  DOI：——

  日期：——