1-(2-(4-nitrophenyl)-2-oxoethyl)pyrrolidine-2,5-dione | 91974-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(4-nitrophenyl)-2-oxoethyl)pyrrolidine-2,5-dione
• 英文别名: 1-[2-(4-Nitrophenyl)-2-oxoethyl]pyrrolidine-2,5-dione
• CAS: 91974-40-2
• 化学式: C₁₂H₁₀N₂O₅
• mdl: MFCD16208535
• 分子量: 262.222
• InChiKey: WZLMYXMAZRSYJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (P-硝基苯基)环氧乙烷 在 potassium dichromate 、 sodium hydroxide 、 硫酸 、 水 作用下， 生成 1-(2-(4-nitrophenyl)-2-oxoethyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Terada, Nippon Kagaku Zasshi, 1956, vol. 77, p. 1265

  摘要：

  DOI：

文献信息

• N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes
  作者：Mahesh H. Shinde、Umesh A. Kshirsagar

  DOI：10.1039/c5ob02034d

  日期：——

  N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base

  已经开发了一种N-溴琥珀酰亚胺（NBS），促进了从商业上可得到的苯乙烯开始合成α-氨基官能化的芳基酮的一种罐策略。NBS参与多项任务，例如形成溴离子，溴代醇的氧化以及提供亲核氮源。通过选择碱，可以容易地在α-亚氨基和α-氨基酮之间切换反应。该一锅策略已成功应用于精神活性药物候选物，安非拉酮，甲氧麻黄酮和4-MEC的合成。
• A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy
  作者：Ting Wei、Yongming Zeng、Wei He、Lili Geng、Liang Hong

  DOI：10.1016/j.cclet.2018.03.031

  日期：2019.2

  Abstract A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot cascade strategy is described. A variety of α-amino ketones are obtained in moderate to good yields under mild conditions. To overcome the multi-step synthesis, N-bromosuccinimide is involved in multiple tasks, playing a key role in the reaction course.

  摘要描述了一种由N-溴代琥珀酰亚胺介导的一锅级联策略将炔烃轻松转化为α-氨基酮的方法。在温和的条件下，以中等至良好的产率获得了多种α-氨基酮。为了克服多步骤合成，N-溴代琥珀酰亚胺涉及多个任务，在反应过程中起关键作用。
• Regioselective Oxo-Amination of Alkenes and Enol Ethers with <i>N</i>-Bromosuccinimide–Dimethyl Sulfoxide Combination: A Facile Synthesis of α-Amino-Ketones and Esters
  作者：Pragati K. Prasad、Rambabu N. Reddi、Arumugam Sudalai

  DOI：10.1021/acs.orglett.5b03540

  日期：2016.2.5

  amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S+–O–Br species generated by the interaction of NBS with DMSO has been proven.

  已经开发出前所未有的烯烃和烯醇醚向相应的α-亚氨基羰基化合物的转化，其具有优异的区域选择性和产率。该羰基化胺化工艺使用现成的N-溴琥珀酰亚胺（NBS）和仲胺作为N源，并使用二甲基亚砜（DMSO）作为氧化剂，而且一步一步还原就可生产氨基醇，从而扩大了范围操作上的简单反应 首次证明了NBS与DMSO相互作用产生的反应性Me 2 S + -O-Br物种的形成。
• [EN] A METAL FREE PROCESS FOR THE PREPARATION OF ALPHA-SUBSTITUTED CARBONYL COMPOUNDS FROM ALKENES<br/>[FR] PROCÉDÉ SANS MÉTAL POUR LA PRÉPARATION DE COMPOSÉS DE CARBONYLE ALPHA-SUBSTITUÉS À PARTIR D'ALCÈNES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2017077550A1

  公开（公告）日：2017-05-11

  The present invention discloses a novel metal free process for the regioselective synthesis of α-substituted carbonyl compounds of formula I from alkene, X is selected from the following compounds (A, B).

  本发明公开了一种新颖的无金属过程，用于从烯烃中选择性合成式I的α-取代羰基化合物，其中X选自以下化合物（A，B）。
• One-Pot Cascade Leading to Direct α-Imidation of Ketones by a Combination of <i>N</i>-Bromosuccinimide and 1,8-Diazabicyclo[5.4.1]undec-7-ene
  作者：Ying Wei、Shaoxia Lin、Fushun Liang

  DOI：10.1021/ol301871s

  日期：2012.8.17

  A one-pot cascade transformation of ketones into alpha-imidoketones has been developed, in which N-bromosuccinimide (NBS) provides both electrophilic bromine and nucleophilic nitrogen sources, and diazabicyclo[5.4.1]undec-7-ene (DBU) functions as a base and a nucleophilic promoter for the activation of NBS. alpha-Bromination is supposed as the key step in the process, which takes place between more electrophilic bromide active species and enolates.