dimethyl 3-(4-nitrophenyl)-1-tosylaziridine-2,2-dicarboxylate | 1309352-94-0

• 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: dimethyl 3-(4-nitrophenyl)-1-tosylaziridine-2,2-dicarboxylate
• 英文别名: Dimethyl 1-(4-methylphenyl)sulfonyl-3-(4-nitrophenyl)aziridine-2,2-dicarboxylate
• CAS: 1309352-94-0
• 化学式: C₁₉H₁₈N₂O₈S
• 分子量: 434.427
• InChiKey: ZAYNIVMDQFTCKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl 3-(4-nitrophenyl)-1-tosylaziridine-2,2-dicarboxylate 、 苯甲醛 在 nickel(II) perchlorate hexahydrate 作用下， 以 甲苯 为溶剂， 反应 1.83h， 以84%的产率得到dimethyl 2-(4-nitrophenyl)-5-phenyl-3-tosyloxazolidine-4,4-dicarboxylate
  参考文献：
  名称：

  Nickel(ii)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydes via selective carbon–carbon bond cleavage

  摘要：

  开发了一种高效且温和的Ni(ClO4)2催化的N-托辛基氮杂环丙烯和醛的[3+2]环加成，通过C–C键断裂进行。该环加成反应具有高的非对映选择性和区域选择性，生成高度取代的1,3-氧杂哌啶。值得注意的是，这种新反应可以轻松扩展到克级规模，而热条件无法实现相同的转化。

  DOI：

  10.1039/c1cc12189h

文献信息

• Construction of thiazines and oxathianes via [3 + 3] annulation of N-tosylaziridinedicarboxylates and oxiranes with 1,4-dithiane-2,5-diol: application towards the synthesis of bioactive molecules
  作者：Rohit Kumar Varshnaya、Prabal Banerjee

  DOI：10.1039/c7ob00941k

  日期：——

  Lewis acid catalyzed [3+3] annulation of N tosylaziridinedicarboxylates and oxiranes with in situ generated mercaptoaldehyde for the synthesis of functionalized thiazine and oxathiane derivatives has been developed. Additionally, this method facilitate the derivatization of thiazine by detosylation and Krapcho monodecarboxylation.

  已经开发了路易斯酸用原位产生的巯基醛催化N甲苯磺酰基氮丙啶二羧酸酯和环氧乙烷的[3 + 3]环合反应，以合成功能化的噻嗪和环氧乙烷衍生物。另外，该方法促进了通过去甲苯磺酸化和Krapcho单脱羧的噻嗪的衍生化。
• Lewis acid-catalyzed [3+3] cycloadditions of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage
  作者：Sang Gyu Lee、Sung-Gon Kim

  DOI：10.1016/j.tet.2018.05.031

  日期：2018.7

  Lewis acid-catalyzed [3 + 3] cycloaddition reaction of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines has been developed for the stereoselective synthesis of tetrahydroisoquinolines (THIQs). The reaction performed using Gd(OTf)3 as the Lewis acid catalyst was tolerant to various N-tosylaziridine and N,N-dialkyl-3-vinylaniline substrates and provided access to highly functionalized THIQs

  已经开发了路易斯酸催化的供体受体氮丙啶与N，N-二烷基-3-乙烯基苯胺的[3 + 3]环加成反应，用于四氢异喹啉（THIQs）的立体选择性合成。使用Gd（OTf）3作为路易斯酸催化剂进行的反应可耐受各种N-甲苯磺酰氮丙啶和N，N-二烷基-3-乙烯基苯胺底物，并提供通常以高收率获得中等官能度至优异非对映选择性的高度官能化THIQs 。
• Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon–carbon bond cleavage
  作者：Lei Li、Xingxing Wu、Junliang Zhang

  DOI：10.1039/c1cc10926j

  日期：——

  A novel, mild, robust catalyst Y(OTf)(3) for C-C bond heterolysis of N-tosyl aziridines was developed and the resulting metallo-azomethine ylides may readily undergo [3+2] dipolar cycloaddition with an electron-rich olefin via a stepwise reaction pathway with high regio- and diastereoselectivity leading to substituted pyrrolidines.

  新型，温和，坚固的催化剂Y（OTf）（3）用于N-甲苯磺酰基氮丙啶的CC键杂化反应，所得的金属-偶氮甲亚胺很容易与富电子烯烃通过[3 + 2]双极性环加成。具有高区域和非对映选择性的逐步反应途径，导致取代的吡咯烷。
• Catalytic C6 Functionalization of 2,3-Disubstituted Indoles by Scandium Triflate
  作者：Hua Liu、Chao Zheng、Shu-Li You

  DOI：10.1021/jo402511b

  日期：2014.2.7

  We report herein an unprecedented direct catalytic C6 functionalization reaction of 2,3-disubstituted indoles with various N–Ts aziridines catalyzed by Sc(OTf)3 under mild conditions. Mechanistic studies revealed that a kinetically favored but reversible formal [3 + 2] annulation occurs initially. The direct C6 functionalization, although having a relatively higher energetic barrier, delivers the thermodynamically

  我们在这里报道了在温和的条件下，由Sc（OTf）3催化的各种N-Ts氮丙啶2，3-二取代的吲哚空前的直接催化C6官能化反应。机理研究表明，动力学上有利但可逆的形式[3 + 2]初始出现。直接的C6功能化尽管具有相对较高的能量屏障，但仍可提供热力学上有利的产品。
• Lewis acid-catalyzed Friedel-Crafts/Michael cascade reaction of N,N-dialkyl-3-vinylanilines with N-tosylaziridines for the stereoselective synthesis of highly functionalized tetrahydroisoquinolines
  作者：Sang Gyu Lee、Seunghui Sin、Seungyeon Kim、Sung-Gon Kim

  DOI：10.1016/j.tetlet.2018.03.004

  日期：2018.4

  A Lewis acid-catalyzed Friedel-Crafts/Michael cascade reaction between N-dialkyl-3-vinylanilines and N-tosylaziridines has been developed for the stereoselective synthesis of tetrahydroisoquinolines (THIQs). The reaction using Gd(OTf)3 as the Lewis acid catalyst was tolerant to the various N-dialkyl-3-vinylaniline and N-tosylaziridine substrates and provided access to 28 new, highly functionalized THIQs

  已经开发了路易斯酸催化的N-二烷基-3-乙烯基苯胺和N-甲苯磺酰氮丙啶之间的弗瑞德-克来福特/迈克尔级联反应，用于立体选择性合成四氢异喹啉（THIQ）。使用Gd（OTf）3作为路易斯酸催化剂的反应可耐受各种N-二烷基-3-乙烯基苯胺和N-甲苯磺酰氮丙啶底物，并提供以典型的高收率获得28种新型，高度官能化的THIQ的途径，且中等至优异非对映选择性。