diethyl 3-methyl-1-tosylaziridine-2,2-dicarboxylate | 1373511-45-5

• 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: diethyl 3-methyl-1-tosylaziridine-2,2-dicarboxylate
• CAS: 1373511-45-5
• 化学式: C₁₆H₂₁NO₆S
• 分子量: 355.412
• InChiKey: YGQPGARSENJRBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.75
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  亚乙基丙二酸二乙酯 在 1,10-菲罗啉 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 diethyl 3-methyl-1-tosylaziridine-2,2-dicarboxylate
  参考文献：
  名称：

  Copper(II) Triflate Catalyzed Amination and Aziridination of 2-Alkyl Substituted 1,3-Dicarbonyl Compounds

  摘要：

  A method to prepare alpha-acyl-beta-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)(2) + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI=NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C-H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the beta-aminatecl adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2-3 equiv was discovered to result in preferential formal aziridination of the C-C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.

  DOI：

  10.1021/ja301415k

文献信息

• Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes
  作者：Ciputra Tejo、Davin Tirtorahardjo、David Philip Day、Dik-Lung Ma、Chung-Hang Leung、Philip Wai Hong Chan

  DOI：10.1071/ch16580

  日期：——

  The synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under Brønsted base-mediated atmospheric conditions is described. The reaction mechanism is thought to involve the formal oxidation of the substrate followed by aziridination of the

  由2-烷基取代的1,3-二羰基化合物和2-酰基取代的1,4-二羰基化合物与芳基磺酰亚氨基碘丁烷（ArSO 2 N）的反应合成α，α-二酰基氮丙啶和α，α，β-三酰基氮丙啶描述了在Brønsted碱介导的大气条件下的= IPh）。据认为，该反应机理涉及底物的形式氧化，然后由高价碘（iii）试剂将随后的α，β-不饱和中间体进行叠氮化。
• Direct Aza-Darzens Aziridination of<i>N</i>-Tosylimines with 2-Bromomalonates for the Synthesis of Highly Functionalized Donor-Acceptor Aziridines
  作者：Xingxing Wu、Lei Li、Junliang Zhang

  DOI：10.1002/adsc.201200628

  日期：2012.12.14

  An approach to highly functionalized donor-acceptor aziridines by the aziridination of N-tosylimines and 2-bromomalonates in the presence of sodium hydride under mild conditions has been developed. The high-yielding reaction has a relatively broad scope and can be easily scaled up to the gram level.

  已经开发了在温和条件下在氢化钠存在下通过N-甲苯磺酰亚胺和2-溴丙二酸酯的叠氮化来高度官能化的供体-受体氮丙啶的方法。高产率反应具有相对广泛的范围，并且可以容易地按比例放大至克级。