1,2-dipropyl-3-ethyldiaziridine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,2-dipropyl-3-ethyldiaziridine
• 英文别名: 1,2-di-n-propyl-3-ethyldiaziridine；3-Ethyl-1,2-dipropyldiaziridine；3-ethyl-1,2-dipropyldiaziridine
• 化学式: C₉H₂₀N₂
• 分子量: 156.271
• InChiKey: ANEGQUMHAXCVKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-dipropyl-3-ethyldiaziridine 、 丁炔二酸二乙酯 在 1-ethyl-3-methylimidazolium hydrogensulfate 作用下， 反应 0.52h， 以62%的产率得到diethyl 1-[3-ethoxy-1-(ethoxycarbonyl)-3-oxoprop-1-enyl]-3-propyl-2,6-diethyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
  参考文献：
  名称：

  1,2-二烷基和1,2,3-三烷基二氮丙啶的新反应：在离子液体中乙炔二羧酸二乙酯作用下的扩环

  摘要：

  在乙二烯二羧酸二乙酯作用于离子中的1,2-二-和1,2,3-三烷基二氮丙啶的作用下，发现了二氮丙啶环扩环的新反应，从而生成1,2,3,6-四氢嘧啶-4,5-二羧酸二乙酯衍生物液体。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.204
• 作为产物：
  描述：

  正丙胺 、 N-chloro-n-propylamine 在 水 、 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以84.5%的产率得到1,2-dipropyl-3-ethyldiaziridine
  参考文献：
  名称：

  Syntheses of 1,2-di- and 1,2,3-trialkyldiaziridines

  摘要：

  The reactions of 1,3,5-trialkylhexahydro-1,3,5-triazines with N-chloroalkylamines resulted in 1,2-dialkyldiaziridines, whereas the reactions of N-chloroalkylamines or N,N-dichloroalkylamines with an excess of primary aliphatic amines gave 1,2,3-trialkyldiaziridines.

  DOI：

  10.1070/mc2005v015n03abeh002107

文献信息

• Reaction of 1,2-Dialkyldiaziridines and 1,2,3-Trialkyldiaziridines with Methyl Propiolate in Ionic Liquids and in Organic Solvents
  作者：Vera Yu. Petukhova、Leonid L. Fershtat、Vadim V. Kachala、Vladimir V. Kuznetsov、Dmitriy V. Khakimov、Tatyana S. Pivina、Nina N. Makhova

  DOI：10.1002/jhet.1079

  日期：2013.3

  An interaction of 1,2‐dialkyldiaziridine and 1,2,3‐trialkyldiaziridine with methyl propiolate was studied both in organic solvent (MeCN, CH2Cl2, C6H6) and in ionic liquids. Earlier unknown linear structures, in which three molecules of methyl propiolate were suited to one diaziridine molecule (adducts 1 : 3), were obtained in MeCN. The diaziridine ring expansion products 1,2,3,4‐tetrahydropyrimidine

  都在有机溶剂（MeCN，CH 2 Cl 2，C 6 H 6）和离子液体中。在MeCN中获得了较早的未知线性结构，其中三个丙酸甲酯分子适合一个二氮丙啶分子（加合物1：3）。二氮丙啶扩环产物1,2,3,4-四氢嘧啶衍生物（加合物1：2），在某些情况下与它们一起在离子液体中获得相同的线性结构。提供了发现的反应机制。反应的区域选择性被认为是由初始二氮丙啶中取代基的结构决定的。这一结论得到了量子化学计算的支持。
• Syntheses of 1,2-di- and 1,2,3-trialkyldiaziridines
  作者：Vladimir V. Kuznetsov、Nina N. Makhova、Dmitrii E. Dmitriev、Victor V. Seregin

  DOI：10.1070/mc2005v015n03abeh002107

  日期：2005.1

  The reactions of 1,3,5-trialkylhexahydro-1,3,5-triazines with N-chloroalkylamines resulted in 1,2-dialkyldiaziridines, whereas the reactions of N-chloroalkylamines or N,N-dichloroalkylamines with an excess of primary aliphatic amines gave 1,2,3-trialkyldiaziridines.
• A new reaction of 1,2-di- and 1,2,3-trialkyldiaziridines: Ring expansion under the action of diethyl acetylenedicarboxylate in ionic liquids
  作者：Yuliya S. Syroeshkina、Vladimir V. Kuznetsov、Vadim V. Kachala、Nina N. Makhova

  DOI：10.1002/jhet.204

  日期：2009.11

  New reaction of diaziridine ring expansion resulting in diethyl 1,2,3,6‐tetrahydropyrimidine‐4,5‐dicarboxylate derivatives was discovered under the action of diethyl acetylenedicarboxylate on 1,2‐di‐ and 1,2,3‐trialkyldiaziridines in ionic liquids. J. Heterocyclic Chem., (2009).

  在乙二烯二羧酸二乙酯作用于离子中的1,2-二-和1,2,3-三烷基二氮丙啶的作用下，发现了二氮丙啶环扩环的新反应，从而生成1,2,3,6-四氢嘧啶-4,5-二羧酸二乙酯衍生物液体。J.杂环化​​学，（2009）。
• High pressure‐assisted synthesis of 1,2,3‐trialkyldiaziridines from N‐chloroalkylamines
  作者：Vladimir V. Kuznetsov、Julia S. Syroeshkina、Dmitrii I. Moskvin、Marina I. Struchkova、Nina N. Makhova、Alexey A. Zharov

  DOI：10.1002/jhet.5570450230

  日期：2008.3

  Abstractmagnified imageNew method for the preparation of 1,2,3‐trialkyldiaziridines 1 in high yields, based on the transformation of N‐chloroalkylamines 3 without using carbonyl compounds in the presence of primary aliphatic amines with the same alkyl fragment, potassium carbonate and a small amount of water in CHCl3 under high pressure (500 MPa), was developed. Diaziridines 1 can be synthesized in the same conditions using a larger amount of potassium carbonate instead of primary aliphatic amines however in lower yields. The kinetic investigations on the synthesis of 1,2‐diethyl‐3‐methyldiaziridine 1a from N‐chloroethylamine 3a have shown that the reaction leading to diaziridine 1a proceeds according to the law of the second order.