1-(2-(naphthalen-2-yl)-2-oxoethyl)pyrrolidine-2,5-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-(naphthalen-2-yl)-2-oxoethyl)pyrrolidine-2,5-dione
• 英文别名: 1-(2-Naphthalen-2-yl-2-oxoethyl)pyrrolidine-2,5-dione
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: SYBRUGFZBGDKAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-溴代丁二酰亚胺(NBS) 、 2-萘乙酮 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85%的产率得到1-(2-(naphthalen-2-yl)-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

• 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）。
• The Significance of the Imidazole Ring in Anticonvulsant Activity of (Arylalkyl)imidazoles
  作者：Ünsal Çaliş、Sevim Dalkara、Mevlüt Ertan、Rümeysa Sunal

  DOI：10.1002/ardp.19883211203

  日期：——

  The imidazole ring in nafimidone [1‐(2‐naphthyl)‐2‐(1‐imidazolyl)ethanone] was substituted with various groups to investigate the significance of the imidazole ring in anticonvulsant activity. For this purpose, some 2‐acetylnaphthalene derivatives and their reduction products were synthesized. Several N‐alkylation methods were used to prepare 2‐acetylnaphthalenes. NaBH4 was used to synthesize their

  Nafimidone [1- (2-萘基)-2- (1-咪唑基) 乙酮] 中的咪唑环被各种基团取代，以研究咪唑环在抗惊厥活性中的重要性。为此，合成了一些 2-乙酰萘衍生物及其还原产物。几种N-烷基化方法用于制备2-乙酰萘。NaBH4 用于合成它们的还原产物。这些化合物的抗惊厥活性通过抗癫痫药物开发计划的 I 期试验确定。
• CALIS, UNSAL;DALKARA, SEVIM;ERTAN, MEVLUT;SUNAL, RUMEYSA, ARCH. PHARM., 321,(1988) N 12, C. 841-846
  作者：CALIS, UNSAL、DALKARA, SEVIM、ERTAN, MEVLUT、SUNAL, RUMEYSA

  DOI：——

  日期：——