1-isopropyl-aziridine | 1072-50-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-isopropyl-aziridine
• 英文别名: 1-Isopropyl-aziridin；2-Ethylenimino-propan；1-Isopropylaziridine；1-propan-2-ylaziridine
• CAS: 1072-50-0
• 化学式: C₅H₁₁N
• 分子量: 85.149
• InChiKey: MMMPMWQSPXSMAH-UHFFFAOYSA-N

物化性质

• 沸点：
  67-68 °C
• 密度：
  0.7511 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 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：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-isopropyl-aziridine 在 三氯化铝 、 苯 作用下， 生成 isopropyl-diphenethyl-amine
  参考文献：
  名称：

  Bras, Doklady Akademii Nauk SSSR, 1952, vol. 87, p. 747,750

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(异丙基氨)乙醇 在 硫酸 作用下， 生成 1-isopropyl-aziridine
  参考文献：
  名称：

  Bras, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 763,764; engl. Ausg. S. 731, 732

  摘要：

  DOI：

文献信息

• Acid-catalyzed decomposition of 1-alkyltriazolines: a mechanistic study
  作者：Richard H. Smith、Brian D. Wladkowski、Jesse E. Taylor、Erin J. Thompson、Brunon Pruski、John R. Klose、A. W. Andrews、Christopher J. Michejda

  DOI：10.1021/jo00060a027

  日期：1993.4

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

  DOI：——

  日期：——
• Bras, Zhurnal Obshchei Khimii, 1955, vol. 25, p. 763,764; engl. Ausg. S. 731, 732
  作者：Bras

  DOI：——

  日期：——
• Bras, Doklady Akademii Nauk SSSR, 1952, vol. 87, p. 747,750
  作者：Bras

  DOI：——

  日期：——