1-(2-hydroxyethyl)-3-methyltriazene | 141849-45-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-hydroxyethyl)-3-methyltriazene
• 英文别名: Ethanol, 2-(3-methyl-1-triazenyl)-；2-(2-methyliminohydrazinyl)ethanol
• CAS: 141849-45-8
• 化学式: C₃H₉N₃O
• 分子量: 103.124
• InChiKey: CGGOPIVLQHSFEK-UHFFFAOYSA-N

物化性质

• 沸点：
  163.7±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-acetyl-1-(2-hydroxyethyl)-3-methyltriazene 在 sodium hydroxide 作用下， 反应 1.0h， 以13%的产率得到1-(2-hydroxyethyl)-3-methyltriazene
  参考文献：
  名称：

  Novel triazenes and triazolines from the base-catalyzed hydrolysis of 1,3-dialkyl-3-acyltriazenes

  摘要：

  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.

  DOI：

  10.1021/jo00050a016

文献信息

• 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.