• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

克服β-硝基烯酮的常见反应性：多官能化的偕丙醇和共轭硝三烯体系的合成。

Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems.

机构信息

Green Chemistry Group, School of Sciences and Technology, Chemistry Division, ChIP Research Center, University of Camerino, Via Madonna delle Carceri, Camerino, Macerata 62032, Italy.

Institute of BioPharmaceutical Research, Liaocheng University, Liaocheng 252059, People's Republic of China.

出版信息

J Org Chem. 2023 Apr 7;88(7):4770-4777. doi: 10.1021/acs.joc.2c02669. Epub 2023 Mar 16.

DOI:10.1021/acs.joc.2c02669
PMID:36926909
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10088019/
Abstract

Herein, we report a new application of β-nitroenones as valuable building blocks for the preparation of polyfunctionalized homoallylic alcohols; they can be used as key precursors of conjugated nitrotriene systems. The synthesis of homoallylic alcohols was performed exploiting the chemoselective addition of metal allylating agents to the ketone moiety vs the nitroalkenyl group. The conversion of alcohols into nitrotrienes was achieved under Lewis-acid-promoted conditions. Both classes of compounds were obtained in good to excellent yields.

摘要

在此，我们报告了β-硝基烯酮作为多功能化偕丙醇制备的有价值的构建块的新应用；它们可用作共轭硝三烯体系的关键前体。通过选择性地将金属烯丙基试剂加成到酮部分而不是硝基烯基来合成偕丙醇。在路易斯酸促进的条件下，将醇转化为硝三烯。这两类化合物都以良好至优异的产率获得。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/9cc0feb4b0dd/jo2c02669_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/2ebe8046d698/jo2c02669_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/0319bf187830/jo2c02669_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/dc5b4c8d6a0c/jo2c02669_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/ac3bdd1096ee/jo2c02669_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/46b716a9de05/jo2c02669_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/6c2f2964f47c/jo2c02669_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/76c9ddf58c4a/jo2c02669_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/f69db79c9a0f/jo2c02669_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/9cc0feb4b0dd/jo2c02669_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/2ebe8046d698/jo2c02669_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/0319bf187830/jo2c02669_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/dc5b4c8d6a0c/jo2c02669_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/ac3bdd1096ee/jo2c02669_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/46b716a9de05/jo2c02669_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/6c2f2964f47c/jo2c02669_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/76c9ddf58c4a/jo2c02669_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/f69db79c9a0f/jo2c02669_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ad5e/10088019/9cc0feb4b0dd/jo2c02669_0005.jpg

相似文献

1
Overcoming the Usual Reactivity of β-Nitroenones: Synthesis of Polyfunctionalized Homoallylic Alcohols and Conjugated Nitrotriene Systems.克服β-硝基烯酮的常见反应性：多官能化的偕丙醇和共轭硝三烯体系的合成。
J Org Chem. 2023 Apr 7;88(7):4770-4777. doi: 10.1021/acs.joc.2c02669. Epub 2023 Mar 16.
2
A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds.从β-硝基烯酮和活性亚甲基化合物出发的多官能化呋喃的新有价值的合成。
Molecules. 2019 Dec 13;24(24):4575. doi: 10.3390/molecules24244575.
3
Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols.β-三甲基硅基、氟化甲基、苯硫基高烯丙醇的巴比尔型反非对映和对映选择性合成。
Sci Rep. 2017 Jul 7;7(1):4873. doi: 10.1038/s41598-017-04986-x.
4
Stereochemical Control via Chirality Pairing: Stereodivergent Syntheses of Enantioenriched Homoallylic Alcohols.手性配对的立体化学控制：对映富集的偕丙醇的立体发散合成。
Angew Chem Int Ed Engl. 2021 Nov 2;60(45):24096-24106. doi: 10.1002/anie.202107004. Epub 2021 Oct 4.
5
Stereoselective synthesis of allylic sulfones via the oxonia-Cope rearrangement of homoallylic alcohols containing a homoallylic sulfone moiety.通过含有高烯丙基砜部分的高烯丙醇的氧化锍-Cope重排反应立体选择性合成烯丙基砜。
J Org Chem. 2006 Jun 23;71(13):4823-8. doi: 10.1021/jo060517e.
6
Application of the lithiation-borylation reaction to the preparation of enantioenriched allylic boron reagents and subsequent in situ conversion into 1,2,4-trisubstituted homoallylic alcohols with complete control over all elements of stereochemistry.将锂化-硼化反应应用于制备对映体富集的烯丙基硼试剂，并随后在原位转化为 1,2,4-三取代的同烯丙基醇，可对立体化学的所有元素进行完全控制。
J Am Chem Soc. 2010 Mar 24;132(11):4025-8. doi: 10.1021/ja910593w.
7
Stereoselective Syntheses of γ,δ-Bifunctionalized Homoallylic Alcohols and Ethers via Chemoselective Allyl Addition to Aldehydes.立体选择性合成γ,δ-双官能化的偕丙基醇和醚通过醛的选择性烯丙基加成反应。
Org Lett. 2019 Dec 20;21(24):9893-9897. doi: 10.1021/acs.orglett.9b03819. Epub 2019 Dec 3.
8
Highly stereoselective syntheses of ()-δ-boryl--homoallylic alcohols allylation with α-boryl-()-crotylboronate.高对映选择性合成（）-δ-硼基--高烯丙醇与α-硼基-()-巴豆基硼酸酯的烯丙基化反应。
Chem Commun (Camb). 2021 Oct 14;57(82):10799-10802. doi: 10.1039/d1cc04058h.
9
Catalytic Regioselective Isomerization of 2,2-Disubstituted Oxetanes to Homoallylic Alcohols.2,2-二取代氧杂环丁烷催化区域选择性异构化为高烯丙醇
Angew Chem Int Ed Engl. 2020 May 4;59(19):7521-7527. doi: 10.1002/anie.201915772. Epub 2020 Mar 12.
10
A modular approach to polyketide building blocks: cycloadditions of nitrile oxides and homoallylic alcohols.聚酮化合物构建模块的模块化方法：腈氧化物与高烯丙醇的环加成反应
Org Lett. 2005 May 12;7(10):2011-4. doi: 10.1021/ol0504953.

本文引用的文献

1
Topochemical polymerizations for the solid-state synthesis of organic polymers.固相合成有机聚合物的拓扑化学聚合。
Chem Soc Rev. 2021 Mar 21;50(6):4062-4099. doi: 10.1039/d0cs00840k. Epub 2021 Feb 5.
2
Mass spectrometry-based study defines the human urine nitrolipidome.基于质谱的研究定义了人类尿液中的硝化脂谱。
Free Radic Biol Med. 2021 Jan;162:327-337. doi: 10.1016/j.freeradbiomed.2020.10.305. Epub 2020 Oct 24.
3
Boosting Conjugate Addition to Nitroolefins Using Lithium Tetraorganozincates: Synthetic Strategies and Structural Insights.
利用四有机锌锂盐促进硝基烯烃的共轭加成：合成策略和结构见解。
Chemistry. 2020 Jul 17;26(40):8742-8748. doi: 10.1002/chem.202001294. Epub 2020 Jun 29.
4
Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols.碱促进的 C-C 键活化实现偕丙醇的自由基烯丙基化反应。
J Am Chem Soc. 2020 Feb 5;142(5):2609-2616. doi: 10.1021/jacs.9b12343. Epub 2020 Jan 27.
5
A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds.从β-硝基烯酮和活性亚甲基化合物出发的多官能化呋喃的新有价值的合成。
Molecules. 2019 Dec 13;24(24):4575. doi: 10.3390/molecules24244575.
6
Total Syntheses of Thailanstatins A-C, Spliceostatin D, and Analogues Thereof. Stereodivergent Synthesis of Tetrasubstituted Dihydro- and Tetrahydropyrans and Design, Synthesis, Biological Evaluation, and Discovery of Potent Antitumor Agents.泰兰他汀 A-C、 splicostatin D 及其类似物的全合成。四取代二氢和四氢吡喃的立体发散合成以及设计、合成、生物评价和发现强效抗肿瘤剂。
J Am Chem Soc. 2018 Jul 5;140(26):8303-8320. doi: 10.1021/jacs.8b04634. Epub 2018 Jun 26.
7
Total Synthesis of Aplysiasecosterol A.阿普司他醇 A 的全合成。
J Am Chem Soc. 2018 Jul 25;140(29):9211-9218. doi: 10.1021/jacs.8b05070. Epub 2018 Jul 11.
8
Palladium-catalyzed anti-Markovnikov hydroalkylation of homoallylic alcohols bearing β-fluorines.钯催化含β-氟的偕丙醇的反马氏羟烷基化反应。
Org Lett. 2013 Sep 6;15(17):4478-81. doi: 10.1021/ol402032a. Epub 2013 Aug 19.
9
Enantio- and regioselective conjugate addition of organometallic reagents to linear polyconjugated nitroolefins.手性和区域选择性的有机金属试剂与线性多共轭硝基烯烃的共轭加成。
Chemistry. 2013 Aug 19;19(34):11352-63. doi: 10.1002/chem.201300538. Epub 2013 Jul 12.
10
Diastereoselective allylation of carbonyl compounds and imines: application to the synthesis of natural products.羰基化合物和亚胺的非对映选择性烯丙基化反应：在天然产物合成中的应用
Chem Rev. 2013 Jul 10;113(7):5595-698. doi: 10.1021/cr400008h. Epub 2013 Mar 29.