1-(2-(4-methoxyphenyl)-2-oxoethyl)pyrrolidine-2,5-dione | 24246-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(4-methoxyphenyl)-2-oxoethyl)pyrrolidine-2,5-dione
• 英文别名: 1-[2-(4-Methoxyphenyl)-2-oxoethyl]pyrrolidine-2,5-dione
• CAS: 24246-91-1
• 化学式: C₁₃H₁₃NO₄
• mdl: MFCD16208534
• 分子量: 247.251
• InChiKey: BRDSEDCKDAUZCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-溴代丁二酰亚胺(NBS) 、 对甲氧基苯乙酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以84%的产率得到1-(2-(4-methoxyphenyl)-2-oxoethyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  One-Pot Cascade Leading to Direct α-Imidation of Ketones by a Combination of N-Bromosuccinimide and 1,8-Diazabicyclo[5.4.1]undec-7-ene

  摘要：

  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.

  DOI：

  10.1021/ol301871s

文献信息

• 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.