1-propylaziridine | 5536-98-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-propylaziridine
• CAS: 5536-98-1
• 化学式: C₅H₁₁N
• 分子量: 85.149
• InChiKey: APKJRCRGAMSYHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-propylaziridine 在 硫化氢 作用下， 生成 2-(丙基氨基)乙硫醇
  参考文献：
  名称：

  Synthesis and Properties of β-sultams

  摘要：

  DOI：

  10.1016/s0040-4039(00)81862-6
• 作为产物：
  描述：

  1-Propyltriazoline 在 水 作用下， 生成 正丙胺 、 2-(丙氨基)乙醇 、 1-propylaziridine 、 乙醛
  参考文献：
  名称：

  Acid-catalyzed decomposition of 1-alkyltriazolines: a mechanistic study

  摘要：

  1-Alkyltriazolines are five-membered cyclic triazenes containing the unusual Z-configuration for the triazene moiety. The hydrolytic decomposition of these compounds in aqueous or mixed acetonitrile-aqueous buffers leads predominantly to the formation of the corresponding 1-alkylaziridines and lesser amounts of 2-(alkylamino)ethanols, alkylamines, and acetaldehyde. The latter two products presumably result from hydrolysis of a rearrangement product, N-ethylidenealkylamine. Neither the nature of the 1-alkyl group nor the pH of the medium greatly influences the product distribution, although decomposition in purely aqueous buffers slightly reduces the aziridine yields. The rate of hydrolysis of 1-alkyltriazolines is about twice as fast as that of the analogous acyclic 1,3,3-trialkyltriazenes and varies in the order tert-butyl > isopropyl > ethyl > butyl > methyl > propyl > benzyl. The mechanism of the decomposition is specific acid-catalyzed (A1) involving rapid reversible protonation followed by rate-limiting formation of a 2-(alkylamino)ethyldiazonium ion. The slopes of the log k(obs) versus pH plots are near -1.0. The solvent deuterium isotope effect, k(H2O)/k(D2O), is in all cases <1.0 and ranges from 0.58 for 1-methyltriazoline to 0.86 for 1-benzyltriazoline. The rate of decomposition shows no significant dependence on the concentration of the buffer acid. The proposed mechanism involves rate-limiting formation of a 2-(alkylamino)ethyldiazonium ion, which is then partitioned among several competing product formation pathways. 1-Alkyltriazolines are potent direct-acting mutagens in the alkylation-sensitive TA 1535 strain of Salmonella typhimurium. A clear, dose-dependent mutagenicity is observed. At the highest dose level, various 1-alkyltriazolines have activities roughly equivalent to that of the potent methylating agent, 1,3-dimethyltriazene. At low levels of substrate, 1-alkyltriazolines are significantly more active than 1,3-dimethyltriazene, with mutagenicity following the order benzyl > methyl > ethyl.

  DOI：

  10.1021/jo00060a027

文献信息

• Nestler,H.J.; Bestian,H., Justus Liebigs Annalen der Chemie, 1974, p. 460 - 467
  作者：Nestler,H.J.、Bestian,H.

  DOI：——

  日期：——
• Marchenko, A. P.; Miroshnichenko, V. V.; Kudryavtsev, A. A., Journal of general chemistry of the USSR, 1984, vol. 54, # 12, p. 2400 - 2405
  作者：Marchenko, A. P.、Miroshnichenko, V. V.、Kudryavtsev, A. A.、Pinchuk, A. M.

  DOI：——

  日期：——
• KOLLER, W.;LINKIES, A.;REHLING, H.;REUSCHLING, D., TETRAHEDRON LETT., 1983, 24, N 21, 2131-2134
  作者：KOLLER, W.、LINKIES, A.、REHLING, H.、REUSCHLING, D.

  DOI：——

  日期：——
• MARCHENKO, A. P.;MIROSHNICHENKO, V. V.;KUDRYAVTSEV, A. A.;PINCHUK, A. M., ZH. OBSHCH. XIMII, 1984, 54, N 12, 2685-2691
  作者：MARCHENKO, A. P.、MIROSHNICHENKO, V. V.、KUDRYAVTSEV, A. A.、PINCHUK, A. M.

  DOI：——

  日期：——
• Synthesis and Properties of β-sultams
  作者：Wolfgang Koller、Adolf Linkies、Herbert Rehling、Dieter Reuschling

  DOI：10.1016/s0040-4039(00)81862-6

  日期：——