N-(2-羟基乙基)-N'-甲基脲 | 58168-06-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 中文名称: N-(2-羟基乙基)-N'-甲基脲
• 英文名称: N-(2-Hydroxyethyl)-N'-methylurea
• 英文别名: 1-(2-hydroxyethyl)-3-methylurea；1-methyl-3-(2-hydroxyethyl)urea
• CAS: 58168-06-2
• 化学式: C₄H₁₀N₂O₂
• mdl: MFCD19159711
• 分子量: 118.136
• InChiKey: NLVGGTZDDAUPNY-UHFFFAOYSA-N

物化性质

• 熔点：
  27-30℃
• 密度：
  1.105

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-羟基乙基)-N'-甲基脲 生成 1-(2-chloroethyl)-3-methylurea
  参考文献：
  名称：

  FUDZIMURA, XADZIMEH;XIRAMATSU, YASUDZO;YABUUTI, TAKAXIRO;XISAKI, MASAKATS+

  摘要：

  DOI：
• 作为产物：
  描述：

  C.I.酸性橙108 、 异氰酸甲酯 以 乙醚 、 苯 为溶剂， 反应 0.5h， 以73%的产率得到N-(2-羟基乙基)-N'-甲基脲
  参考文献：
  名称：

  Cyclization of (2-hydroxyethyl)urea derivatives to give 3-nitroso-2-oxazolidinones under usual nitrosation conditions.

  摘要：

  (2-羟乙基)脲衍生物(Ia-e)在酸的存在下与亚硝酸钠反应，或在氯仿中与亚硝基氯反应，得到了3-亚硝基-2-噁唑烷酮(IIa-e)，产率为10-77%。这些3-亚硝基-2-噁唑烷酮在甲醇中与氯化氢脱亚硝，得到相应的2-噁唑烷酮(IIIa-e)，产率为35-60%。一种N,N-二取代脲，即1-(2-羟乙基)-1-甲基脲(If)在相同条件下也环化，生成3-甲基-2-噁唑烷酮(IIf)。文中讨论了这种环化反应的机制。

  DOI：

  10.1248/cpb.33.497

文献信息

• HETEROCYCLIC COMPOUNDS AND USES THEREOF
  申请人：Ren Pingda

  公开号：US20120122838A1

  公开（公告）日：2012-05-17

  Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

  调节激酶活性的化合物和药物组合物，包括PI3激酶活性，以及与激酶活性相关的疾病和病况的化合物、药物组合物和治疗方法在此进行描述。
• 4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxy-, N-hydroxy-, and N-aminoalkylureas 2. α-Ureidoalkylation of N-(hydroxyalkyl)ureas
  作者：A. N. Kravchenko、A. S. Sigachev、P. A. Belyakov、M. M. Ilyin、K. A. Lyssenko、V. A. Davankov、O. V. Lebedev、N. N. Makhova、V. A. Tartakovsky

  DOI：10.1007/s11172-009-0165-5

  日期：2009.6

  The α-ureidoalkylation of N-(hydroxyalkyl)ureas (ureido alcohols) with 1,3-H2- and 1,3-Me2-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils decrease both in going from 1,3-H2- to 1,3-Me2-4,5-dihydroxyimidazolidin-2-one and with increasing length (or with branching) of the hydroxyalkyl chain in ureido alcohols. The optimal reaction time for ureido alcohols is 1 h. The X-ray diffraction study showed that 2-(2-hydroxy-1,1-dimethylethyl)glycoluril crystallizes as a conglomerate. The enantiomeric analysis of 2-(2-hydroxyethyl)glycoluril was carried out by chiral-phase HPLC.

  系统研究了 N-（羟基烷基）脲（脲醇）与 1,3-H2- 和 1,3-Me2-4,5- 二羟基咪唑烷-2-酮的 α-ureido 烷基化反应。从 1,3-H2- 到 1,3-Me2-4,5-二羟基咪唑烷-2-酮的过程中，以及随着脲基乙醇中羟基烷基链长度（或分支）的增加，糖醛酸的产量都会降低。X 射线衍射研究表明，2-(2-羟基-1,1-二甲基乙基)甘氨酰脲结晶为团聚体。采用手性相高效液相色谱法对 2-(2-羟乙基)甘氨酰脲进行了对映体分析。
• 1,3-Dialkyl-3-acyltriazenes: products and rates of decomposition in acidic and neutral aqueous solutions
  作者：Richard H. Smith、Brian D. Wladkowski、Julie A. Herling、Timothy D. Pfaltzgraff、Brunon Pruski、John Klose、Christopher J. Michejda

  DOI：10.1021/jo00028a047

  日期：1992.1

  The products and mechanism of hydrolytic decomposition of a series of 1,3-dialkyl-3-acyltriazenes were studied in both acidic and neutral buffers. In the acidic region, the products are alkyl alcohols derived from the N(1) alkyl group and amides derived from the intact N(3) portion of the molecule. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is less than 1.0. The mechanism is specific acid catalyzed, involving rapid reversible protonation of the 3-acyl group followed by scission of the N(2)-N(3) bond to generate an amide and an alkyl diazonium ion. The (2-hydroxyethyl)diazonium ion gives ethylene glycol and acetaldehyde, while the (2-chloroethyl)diazonium ion yields 2-chloroethanol. In the neutral region, the products are similar to those found in acidic buffers, alkyl alcohols, and amides. At this pH the (2-chloroethyl)diazonium ion produces ethylene glycol and acetaldehyde in addition to 2-chloroethanol. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is greater than 1.0. The mechanism involves unimolecular heterolysis of the N(2)-N(3) bond to form an amide anion and an alkyldiazonium ion. The methyldiazonium ion leads to incorporation of deuterium in the methyl group of the products, indicating the existence of an equilibrium between the metastable methyldiazonium ion and diazomethane.
• Novel triazenes and triazolines from the base-catalyzed hydrolysis of 1,3-dialkyl-3-acyltriazenes
  作者：Richard H. Smith、Brian D. Wladkowski、Julie A. Herling、Timothy D. Pfaltzgraff、Jesse E. Taylor、Erin J. Thompson、Brunon Pruski、John R. Klose、Christopher J. Michejda

  DOI：10.1021/jo00050a016

  日期：1992.11

  The products and mechanism of hydrolytic decomposition of a series of 1,3-dialkyl-3-acyltriazenes were studied in alkaline buffers. In general the mechanism of decomposition involves deacylation leading to the formation of the parent 1,3-dialkyltriazene. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is less than 1.0, indicating specific base catalysis. A plausible mechanistic explanation is rapid reversible attack by hydroxide ion, followed by rate-limiting heterolysis of the N(l)-acyl bond. The resultant, 1,3-dialkyltriazene is somewhat unstable under the reaction conditions and undergoes subsequent hydrolysis, a reaction previously shown to be specific acid-catalyzed. When the N(l) alkyl group is 2-chloroethyl, unusual products are obtained. For the 3-acetyl and 3-carbethoxy derivatives, the initial deacylation product, 1-(2-chloroethyl)-3-methyltriazene, efficiently cyclizes to form 1-methyltriazoline. The 3-(methylcarbamoyl) derivative does not deacylate, but instead undergoes dehydrohalogenation to 1-vinyl-3-methyl-3-(methylcarbamoyl)triazene.
• Decomposition of 1-nitroso-1-alkyl-3-(2-hydroxyalkyl)ureas
  作者：Joseph E. Saavedra

  DOI：10.1021/jo00313a027

  日期：1990.12