新型三氟甲基化胺酮衍生物的合成、表征和x射线晶体学研究

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-01-02 DOI:10.1080/00397911.2024.2429146

Labet B. Marpna , Tara. R. A. Sangma , Shunan Kaping , Anitha Kandasamy , Jai N. Vishwakarma

{"title":"新型三氟甲基化胺酮衍生物的合成、表征和x射线晶体学研究","authors":"Labet B. Marpna , Tara. R. A. Sangma , Shunan Kaping , Anitha Kandasamy , Jai N. Vishwakarma","doi":"10.1080/00397911.2024.2429146","DOIUrl":null,"url":null,"abstract":"<div><div>Enaminones are important synthetic intermediates for the construction of diverse heterocyclic scaffolds owing to their push-pull electronic structures. A series of novel (Z)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(aryl/alkyl)prop-2-en-1-ones (<strong>5, 6</strong>) and (Z)-3-(aryl/alkylamino)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-ones (<strong>9</strong>, <strong>10</strong>) were synthesized with (E)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(dimethylamino)prop-2-en-1-one (<strong>2</strong>) & (E)-3-(dimethylamino)-1-(4-(trifluoromethyl)phenyl) prop-2-en-1-one (<strong>8</strong>) as starting materials. The structures of the fluorinated enaminones were established with the help of spectral and analytical data. X-ray crystallographic study for a model compound (<strong>6a</strong>) gave a vivid image showing the existence of the product in Z-form unlike the corresponding intermediate that exists in E-form.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 1","pages":"Pages 32-43"},"PeriodicalIF":1.8000,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Aza-Michael addition-elimination led synthesis, characterization and X-ray crystallography of novel trifluoromethylated-enaminone derivatives\",\"authors\":\"Labet B. Marpna , Tara. R. A. Sangma , Shunan Kaping , Anitha Kandasamy , Jai N. Vishwakarma\",\"doi\":\"10.1080/00397911.2024.2429146\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Enaminones are important synthetic intermediates for the construction of diverse heterocyclic scaffolds owing to their push-pull electronic structures. A series of novel (Z)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(aryl/alkyl)prop-2-en-1-ones (<strong>5, 6</strong>) and (Z)-3-(aryl/alkylamino)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-ones (<strong>9</strong>, <strong>10</strong>) were synthesized with (E)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(dimethylamino)prop-2-en-1-one (<strong>2</strong>) & (E)-3-(dimethylamino)-1-(4-(trifluoromethyl)phenyl) prop-2-en-1-one (<strong>8</strong>) as starting materials. The structures of the fluorinated enaminones were established with the help of spectral and analytical data. X-ray crystallographic study for a model compound (<strong>6a</strong>) gave a vivid image showing the existence of the product in Z-form unlike the corresponding intermediate that exists in E-form.</div></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":\"55 1\",\"pages\":\"Pages 32-43\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2025-01-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0039791124001395\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0039791124001395","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

胺酮具有推挽式电子结构，是构建各种杂环支架的重要合成中间体。以(E)-1-（3,5-双（三氟甲基）苯基）-3-（芳基/烷基）-1-（4-（三氟甲基）苯基）-3-（二甲氨基）pro2 -en-1-one(2)和(Z)-3-（芳基/烷基）pro2 -en-1-one（5,6）和(Z)-3-（芳基/烷基）pro2 -en-1-one（9,10）为原料合成了一系列新的(Z)-1-（3,5-双（三氟甲基）苯基）pro2 -en-1-one (2) &；(E)-3-（二甲氨基）-1-（4-（三氟甲基）苯基）prop-2-en-1-one(8)为起始原料。利用光谱和分析数据确定了氟化胺酮的结构。模型化合物（6a）的x射线晶体学研究给出了一个生动的图像，显示该产物以z型存在，而不像相应的中间体以e型存在。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Aza-Michael addition-elimination led synthesis, characterization and X-ray crystallography of novel trifluoromethylated-enaminone derivatives

Enaminones are important synthetic intermediates for the construction of diverse heterocyclic scaffolds owing to their push-pull electronic structures. A series of novel (Z)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(aryl/alkyl)prop-2-en-1-ones (5, 6) and (Z)-3-(aryl/alkylamino)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-ones (9, 10) were synthesized with (E)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(dimethylamino)prop-2-en-1-one (2) & (E)-3-(dimethylamino)-1-(4-(trifluoromethyl)phenyl) prop-2-en-1-one (8) as starting materials. The structures of the fluorinated enaminones were established with the help of spectral and analytical data. X-ray crystallographic study for a model compound (6a) gave a vivid image showing the existence of the product in Z-form unlike the corresponding intermediate that exists in E-form.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.