Dimethyl 3-(4-chlorophenyl)-1-(4-methylphenyl)sulfonylaziridine-2,2-dicarboxylate | 1309352-92-8

• 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-chlorophenyl)-1-(4-methylphenyl)sulfonylaziridine-2,2-dicarboxylate
• CAS: 1309352-92-8
• 化学式: C₁₉H₁₈ClNO₆S
• 分子量: 423.874
• InChiKey: ANQUQAMKZJKZRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 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：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  异氰酸叔丁酯 、 Dimethyl 3-(4-chlorophenyl)-1-(4-methylphenyl)sulfonylaziridine-2,2-dicarboxylate 在 yttrium(III) trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以82%的产率得到dimethyl 3,4-bis(tert-butylimino)-5-(4-chlorophenyl)-1-tosylpyrrolidine-2,2-dicarboxylate
  参考文献：
  名称：

  路易斯酸催化的[3 + 1 + 1]偶氮甲亚胺与异氰酸酯的环加成反应

  摘要：

  已经开发了路易斯酸催化的脂族异氰酸酯与由氮丙啶原位生成的偶氮甲亚胺之间的[3 + 1 + 1]环加成反应，从而生成吡咯烷衍生物。该反应在温和条件下平稳进行，也可以通过[3 + 1]环加成反应，通过使用芳香族异氰化物生成四元杂环氮杂环丁烷进行修饰。

  DOI：

  10.1016/j.tet.2014.06.118

文献信息

• Y(OTf)3-Catalyzed Diastereoselective [3+2] Cycloaddition of N-Tosyl­aziridines and Imines; Efficient Synthesis of Multisubstituted Imidazolidines
  作者：Junliang Zhang、Xingxing Wu

  DOI：10.1055/s-0031-1290816

  日期：2012.7

  Abstract An efficient Y(OTf)3-catalyzed generation of azometh­ine ylides from donor–acceptor aziridines and their [3+2] cyclo­addition with imines was developed. The method provides facile access to multisubstituted imidazolidines, which have been extensively used in organic synthesis. Furthermore, a three-component reaction on a gram scale and an asymmetric variation were also developed in this work

  摘要 开发了一种高效的Y（OTf）3催化的供体-受体氮丙啶及其衍生物与亚胺的[3 + 2]环加成反应生成亚甲亚胺基化物。该方法提供了容易地获得已广泛用于有机合成中的多取代的咪唑烷的方法。此外，这项工作还发展了克级的三组分反应和不对称变化。 开发了一种高效的Y（OTf）3催化的供体-受体氮丙啶及其衍生物与亚胺的[3 + 2]环加成反应生成亚甲亚胺基化物。该方法提供了容易地获得已广泛用于有机合成中的多取代的咪唑烷的方法。此外，这项工作还发展了克级的三组分反应和不对称变化。
• Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel–Crafts Reactions of Donor–Acceptor Aziridines with N,N-Dialkylanilines
  作者：Yerin Kim、Yong Il Kwon、Sung-Gon Kim

  DOI：10.1055/s-0039-1690731

  日期：2020.1

  A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel–Crafts reaction of donor­–acceptor aziridines with N,N-dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88%), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich

  提出了一种通过路易斯酸催化的供体-受体氮丙啶与N，N-二烷基苯胺的弗里德-克来夫特反应高效，温和地合成二芳基甲胺骨架的方法，该方法可以高产率（高达88％）提供生物学上重要的二芳基甲胺衍生物。该反应适合于合成各种二芳基甲胺衍生物，并且对于包括二甲氧基苯在内的富电子芳烃具有广阔的范围。
• 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。
• Nickel(ii)-catalyzed diastereoselective [3+2] cycloaddition of N-tosyl-aziridines and aldehydes via selective carbon–carbon bond cleavage
  作者：Xingxing Wu、Lei Li、Junliang Zhang

  DOI：10.1039/c1cc12189h

  日期：——

  An efficient and mild Ni(ClO4)2-catalyzed [3+2] cycloaddition of N-tosylaziridines and aldehydesvia C–C bond cleavage was developed. The cycloaddition reaction proceeds with high diastereoselectivity and regioselectivity leading to highly substituted 1,3-oxazolidines. Notably, this novel reaction can be easily expanded to gram level scale and the thermal conditions cannot achieve the same transformation.

  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。