1-ethyl-5,6-dihydro-4H-triazine | 199595-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1-ethyl-5,6-dihydro-4H-triazine
• CAS: 199595-92-1
• 化学式: C₅H₁₁N₃
• 分子量: 113.162
• InChiKey: MITKKSUTLMLXMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  140.7±23.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  28
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethyl-5,6-dihydro-4H-triazine 在 氘氧化钠 、 sodium phosphate 作用下， 以 氘代乙腈 、 重水 为溶剂， 反应 5.0h， 以44.7%的产率得到3-(乙基氨基)-1-丙醇
  参考文献：
  名称：

  Triazinines:  Synthesis and Proteolytic Decomposition of a New Class of Cyclic Triazenes

  摘要：

  The reaction of 1-azido-3-chloropropane with various Grignard reagents and subsequent treatment with anhydrous isopropylamine results in the formation of the corresponding azimine. If the initial magnesium-triazene complex is first hydrolyzed with Dowex resin and then concentrated, the resultant linear triazene begins self-catalyzed cyclization to form the six-membered-ring triazenes as the major product, with HCl as the byproduct. Addition of an amine, at reduced temperature, allows for the neutralization of the byproduct, HCl, which would otherwise react with the linear triazene and the cyclic six-membered-ring triazene to form hydrolysis products. We have assigned the trivial name of triazinines to this new class of cyclic triazenes. The hydrolytic decomposition of these compounds in mixed acetonitrile-aqueous buffers predominantly forms 3-(alkylamino)-1-propanol and lesser amounts of the rearranged alcohol 1-(alkylamino)-2-propanol and N-alkyl-2-propenamine. The rate of hydrolysis of 1-alkyltriazinines is approximately equal to that of the analogous 1,3,3-trialkyltriazenes, about three times slower than that of the analogous 1-alkyltriazolines, and varies in the order ethyl > butyl > 3,3-diethoxypropyl > benzyl, As was true for other triazenes, the mechanism of the decomposition was found to be specific acid-catalyzed (Al), involving rapid reversible protonation followed by rate-limiting formation of a 3-(alkylamino)propyldiazonium ion. The slopes of the log k(obs) versus pH plots were near -1.0. The solvent deuterium isotope effect, k(H2O)/k(D2O), was in all cases <1.0 and ranges from 0.82 for 1-benzyltriazinine to 0.89 for 1-ethyltriazinine. The activation parameters of the proteolytic decomposition of a series, 1-ethyltriazinine, 1-ethyltriazoline, 1,3,3-triethyltriazene, and 1-ethyl-3-methyltriazene, had similar values for Delta H-double dagger (+9 --> 12 kcal/mol) and Delta S-double dagger (+7 --> 15 eu), respectively.

  DOI：

  10.1021/jo970721p
• 作为产物：
  描述：

  1-叠氮基-3-氯丙烷 、 乙基氯化镁 以 四氢呋喃 为溶剂， 反应 0.75h， 以31%的产率得到1-ethyl-5,6-dihydro-4H-triazine
  参考文献：
  名称：

  Triazinines:  Synthesis and Proteolytic Decomposition of a New Class of Cyclic Triazenes

  摘要：

  The reaction of 1-azido-3-chloropropane with various Grignard reagents and subsequent treatment with anhydrous isopropylamine results in the formation of the corresponding azimine. If the initial magnesium-triazene complex is first hydrolyzed with Dowex resin and then concentrated, the resultant linear triazene begins self-catalyzed cyclization to form the six-membered-ring triazenes as the major product, with HCl as the byproduct. Addition of an amine, at reduced temperature, allows for the neutralization of the byproduct, HCl, which would otherwise react with the linear triazene and the cyclic six-membered-ring triazene to form hydrolysis products. We have assigned the trivial name of triazinines to this new class of cyclic triazenes. The hydrolytic decomposition of these compounds in mixed acetonitrile-aqueous buffers predominantly forms 3-(alkylamino)-1-propanol and lesser amounts of the rearranged alcohol 1-(alkylamino)-2-propanol and N-alkyl-2-propenamine. The rate of hydrolysis of 1-alkyltriazinines is approximately equal to that of the analogous 1,3,3-trialkyltriazenes, about three times slower than that of the analogous 1-alkyltriazolines, and varies in the order ethyl > butyl > 3,3-diethoxypropyl > benzyl, As was true for other triazenes, the mechanism of the decomposition was found to be specific acid-catalyzed (Al), involving rapid reversible protonation followed by rate-limiting formation of a 3-(alkylamino)propyldiazonium ion. The slopes of the log k(obs) versus pH plots were near -1.0. The solvent deuterium isotope effect, k(H2O)/k(D2O), was in all cases <1.0 and ranges from 0.82 for 1-benzyltriazinine to 0.89 for 1-ethyltriazinine. The activation parameters of the proteolytic decomposition of a series, 1-ethyltriazinine, 1-ethyltriazoline, 1,3,3-triethyltriazene, and 1-ethyl-3-methyltriazene, had similar values for Delta H-double dagger (+9 --> 12 kcal/mol) and Delta S-double dagger (+7 --> 15 eu), respectively.

  DOI：

  10.1021/jo970721p

文献信息

• Triazinines:  Synthesis and Proteolytic Decomposition of a New Class of Cyclic Triazenes
  作者：Brigitte F. Schmidt、Emily J. Snyder、Robin M. Carroll、David W. Farnsworth、Christopher J. Michejda、Richard H. Smith

  DOI：10.1021/jo970721p

  日期：1997.12.1

  The reaction of 1-azido-3-chloropropane with various Grignard reagents and subsequent treatment with anhydrous isopropylamine results in the formation of the corresponding azimine. If the initial magnesium-triazene complex is first hydrolyzed with Dowex resin and then concentrated, the resultant linear triazene begins self-catalyzed cyclization to form the six-membered-ring triazenes as the major product, with HCl as the byproduct. Addition of an amine, at reduced temperature, allows for the neutralization of the byproduct, HCl, which would otherwise react with the linear triazene and the cyclic six-membered-ring triazene to form hydrolysis products. We have assigned the trivial name of triazinines to this new class of cyclic triazenes. The hydrolytic decomposition of these compounds in mixed acetonitrile-aqueous buffers predominantly forms 3-(alkylamino)-1-propanol and lesser amounts of the rearranged alcohol 1-(alkylamino)-2-propanol and N-alkyl-2-propenamine. The rate of hydrolysis of 1-alkyltriazinines is approximately equal to that of the analogous 1,3,3-trialkyltriazenes, about three times slower than that of the analogous 1-alkyltriazolines, and varies in the order ethyl > butyl > 3,3-diethoxypropyl > benzyl, As was true for other triazenes, the mechanism of the decomposition was found to be specific acid-catalyzed (Al), involving rapid reversible protonation followed by rate-limiting formation of a 3-(alkylamino)propyldiazonium ion. The slopes of the log k(obs) versus pH plots were near -1.0. The solvent deuterium isotope effect, k(H2O)/k(D2O), was in all cases <1.0 and ranges from 0.82 for 1-benzyltriazinine to 0.89 for 1-ethyltriazinine. The activation parameters of the proteolytic decomposition of a series, 1-ethyltriazinine, 1-ethyltriazoline, 1,3,3-triethyltriazene, and 1-ethyl-3-methyltriazene, had similar values for Delta H-double dagger (+9 --> 12 kcal/mol) and Delta S-double dagger (+7 --> 15 eu), respectively.