trans-2-(4-nitrophenyl)-3-phenyl-1-tosylaziridine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-2-(4-nitrophenyl)-3-phenyl-1-tosylaziridine
• 英文别名: 2-(4-nitrophenyl)-3-phenyl-1-tosylaziridine；(2R,3R)-1-(4-methylphenyl)sulfonyl-2-(4-nitrophenyl)-3-phenylaziridine
• 化学式: C₂₁H₁₈N₂O₄S
• 分子量: 394.451
• InChiKey: BELYLUOSPBORLU-JAZPPYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 在 aluminum (III) chloride 、 四(二甲氨基)乙烯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 trans-2-(4-nitrophenyl)-3-phenyl-1-tosylaziridine 、 cis-2-(4-nitrophenyl)-3-phenyl-1-tosylaziridine
  参考文献：
  名称：

  TDAE Strategy for the Synthesis of 2,3-Diaryl N-Tosylaziridines

  摘要：

  本文报道了一种新颖且快速的合成2,3-二芳基N-甲苯磺酰氮丙啶的方法，该方法采用TDAE策略，以邻位或对位硝基（二氯甲基）苯衍生物和N-甲苯磺酰亚胺为起始物。从1-（二氯甲基）-4-硝基苯中分离出顺反异构体混合物，而从邻硝基衍生物中仅获得了反式氮丙啶。

  DOI：

  10.3390/molecules18077364

文献信息

• Quantification of the Electrophilic Reactivities of Aldehydes, Imines, and Enones
  作者：Roland Appel、Herbert Mayr

  DOI：10.1021/ja200820m

  日期：2011.6.1

  of the aziridination reactions of aldimines, and of the cyclopropanation reactions of α,β-unsaturated ketones with aryl-stabilized dimethylsulfonium ylides have been determined photometrically in dimethyl sulfoxide (DMSO). All of these sulfur ylide-mediated cyclization reactions as well as the addition reactions of stabilized carbanions to N-tosyl-activated aldimines have been shown to follow a second-order

  醛的环氧化反应、醛亚胺的氮丙啶化反应以及 α,β-不饱和酮与芳基稳定的二甲基锍叶立德的环丙烷化反应的速率已在二甲基亚砜 (DMSO) 中通过光度法测定。所有这些硫叶立德介导的环化反应以及稳定的碳负离子与 N-甲苯磺酰基活化的醛亚胺的加成反应都已显示遵循二级速率定律，其中速率常数反映了（初始）CC 键之间的形成亲核试剂和亲电试剂。导出的二阶速率常数 (log k(2)) 已与芳基稳定的硫叶立德 4a 的已知亲核性参数 (N, s(N)) 相结合，b 和受体取代的碳负离子 4c-h 以计算芳香族和脂肪族醛 (1a-i)、N-受体取代的芳香醛亚胺 (2a-e) 和 α,β-不饱和酮 (3a) 的亲电性参数 E -f) 根据 J. Am. 中定义的线性自由能关系 log k(2) = s(N)(N + E)。化学 Soc.2001, 123, 9500-9512。这项工作中报告的数据首次定量比较了
• Synthesis of<i>C</i>₂-Symmetric Sulfide and Its First Application in Highly Enantioselective Synthesis of Chiral Aziridines
  作者：Yuan Gui、Sheng Shen、Hai-Yang Wang、Zhi-Yi Li、Zhi-Zhen Huang

  DOI：10.1246/cl.2007.1436

  日期：2007.12.5

  A C 2 -symmetric sulfide 6 has been synthesized from cheap L-tartaric acid. It was found that sulfide 6 could perform a tandem reaction with benzyl bromide and tosyl imines to give (2S,3S)-aziridines 9a-9g with good to excellent enantioseletivities (up to 96% ee).

  AC 2 -对称硫化物6已由廉价的L-酒石酸合成。发现硫化物 6 可以与苄基溴和甲苯磺酰亚胺进行串联反应，得到 (2S,3S)-氮丙啶 9a-9g，具有良好至极好的对映选择性（高达 96% ee）。
• Phosphite-mediated annulation: an efficient protocol for the synthesis of multi-substituted cyclopropanes and aziridines
  作者：Xu-Guang Liu、Yin Wei、Min Shi

  DOI：10.1016/j.tet.2009.10.099

  日期：2010.1

  In the presence of phosphite or phosphine, the reaction between 4-, 2-nitrobenzaldehyde and methylidenemalononitriles proceeded smoothly to give the cyclopropane derivatives in high yields, while the reaction between 4-, 2-benzaldehyde, and N-tosylbenzaldimines afforded the azidridine derivatives in moderate to high yields. A plausible mechanism was proposed and the strongly electron-withdrawing nitro-group is believed to play a critical role in these transformations. (C) 2009 Elsevier Ltd. All rights reserved.
• Two-Step Asymmetric Synthesis of Disubstituted <i>N</i>-Tosyl Aziridines Having 98−100% ee:  Use of a Phosphazene Base
  作者：Arlette Solladié-Cavallo、Marin Roje、Richard Welter、Vitomir Šunjić

  DOI：10.1021/jo035586x

  日期：2004.2.1

  Unknown diaryl (1-3) and alkyl-phenyl (4, 5) N-tosyl aziridines have been successfully synthesized from pure (R,R,R,Ss)-(-)-sulfonium salt derived from Eliel's oxathiane, tosylimines 11a-f, and using a phosphazene base (EtP2) to generate the ylide. Both cis and trans aziridines have exceptionally high enantiomeric purities (98.7-99.9%). The (2R,3R)-configuration of trans-3 and the (2R,3S)-configuration of cis-4 have been determined by X-ray analysis using the Bijvoet method. The R-configuration found at C2 is consistent with the model and all previous results, therefore all trans-aziridines and cis-aziridines have been assigned the (2R,3R)- and the (2R,3S)-configurations, respectively. This two-step asymmetric synthesis can be easily used on gram quantities and involves no unstable/hazardous reagent. The chiral auxiliary is used in a stoichiometric amount but is recovered in high yield and reused.
• TDAE Strategy for the Synthesis of 2,3-Diaryl N-Tosylaziridines
  作者：Omar Khoumeri、Cédric Spitz、Thierry Terme、Patrice Vanelle

  DOI：10.3390/molecules18077364

  日期：——

  We report herein an original and rapid synthesis of 2,3-diaryl N-tosylaziridines by TDAE strategy starting from ortho- or para-nitro(dichloromethyl)benzene derivatives and N-tosylimines. A mixture of cis/trans isomers was isolated from 1-(dichloromethyl)-4-nitrobenzene, whereas only trans-aziridines were obtained from ortho-nitro derivatives.

  本文报道了一种新颖且快速的合成2,3-二芳基N-甲苯磺酰氮丙啶的方法，该方法采用TDAE策略，以邻位或对位硝基（二氯甲基）苯衍生物和N-甲苯磺酰亚胺为起始物。从1-（二氯甲基）-4-硝基苯中分离出顺反异构体混合物，而从邻硝基衍生物中仅获得了反式氮丙啶。