1-(2-Hydroxyethyl)-3-benzyl-3-(methylcarbamoyl)triazene | 137668-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-Hydroxyethyl)-3-benzyl-3-(methylcarbamoyl)triazene
• 英文别名: 1-Benzyl-1-(2-hydroxyethyldiazenyl)-3-methylurea；1-benzyl-1-(2-hydroxyethyldiazenyl)-3-methylurea
• CAS: 137668-38-3
• 化学式: C₁₁H₁₆N₄O₂
• 分子量: 236.274
• InChiKey: MABBNNSGHMPMBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-Hydroxyethyl)-3-benzyl-3-(methylcarbamoyl)triazene 在 水 作用下， 以 乙腈 为溶剂， 生成 1-苄基-3-甲基脲 、 乙二醇 、 乙醛
  参考文献：
  名称：

  1,3-Dialkyl-3-acyltriazenes: products and rates of decomposition in acidic and neutral aqueous solutions

  摘要：

  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.

  DOI：

  10.1021/jo00028a047

文献信息

• 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.