• 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

手性镍(II)配合物催化对映选择性一锅法合成4-色烯衍生物

Enantioselective one-pot synthesis of 4-chromene derivatives catalyzed by a chiral Ni(ii) complex.

作者信息

Yu Xuan, Lan Wenjie, Li Jiaqi, Bai Hui, Qin Zhaohai, Fu Bin

机构信息

Department of Applied Chemistry, China Agricultural University West Yuanmingyuan Rd. 2 Beijing 100193 People's Repubic of China

出版信息

RSC Adv. 2020 Dec 16;10(72):44437-44441. doi: 10.1039/d0ra08906k. eCollection 2020 Dec 9.

DOI:10.1039/d0ra08906k
PMID:35517147
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9058437/
Abstract

A Ni(ii)-bis(oxazoline) complex and -TSOH are used to form enantioenriched 4-chromenes from -quinone methides (-QMs) and dicarbonyls, providing the desired products in up to 95% ee. The method is compatible with various β-ketoester substrates, and the products obtained could be converted into biologically active 4-chromene derivatives.

摘要

一种镍(II)-双恶唑啉配合物和对甲苯磺酸用于从醌甲基化物(-QMs)和二羰基化合物形成对映体富集的4-色烯,以高达95%的对映体过量提供所需产物。该方法与各种β-酮酯底物兼容,所得产物可转化为具有生物活性的4-色烯衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/4041601f7784/d0ra08906k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/39fdef4dfae4/d0ra08906k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/180ab0789473/d0ra08906k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/db07f112144e/d0ra08906k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/84f5d8a41a9e/d0ra08906k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/f6a719a170e0/d0ra08906k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/4041601f7784/d0ra08906k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/39fdef4dfae4/d0ra08906k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/180ab0789473/d0ra08906k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/db07f112144e/d0ra08906k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/84f5d8a41a9e/d0ra08906k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/f6a719a170e0/d0ra08906k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3bc/9058437/4041601f7784/d0ra08906k-s4.jpg

相似文献

1
Enantioselective one-pot synthesis of 4-chromene derivatives catalyzed by a chiral Ni(ii) complex.手性镍(II)配合物催化对映选择性一锅法合成4-色烯衍生物
RSC Adv. 2020 Dec 16;10(72):44437-44441. doi: 10.1039/d0ra08906k. eCollection 2020 Dec 9.
2
Brønsted acid catalyzed, conjugate addition of β-dicarbonyls to in situ generated ortho-quinone methides--enantioselective synthesis of 4-aryl-4H-chromenes.布朗斯特酸催化的β-二羰基化合物与原位生成的邻醌甲醚的共轭加成反应——4-芳基-4H-色烯的对映选择性合成。
Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7923-7. doi: 10.1002/anie.201403573. Epub 2014 Jun 18.
3
Vinylidene -Quinone Methides: Unique Chiral Reaction Intermediates in Catalytic Asymmetric Synthesis.亚乙烯基-醌甲基化物:催化不对称合成中独特的手性反应中间体
Chimia (Aarau). 2018 Dec 19;72(12):892-899. doi: 10.2533/chimia.2018.892.
4
Enantioselective one-pot synthesis of 2-amino-4-(indol-3-yl)-4H-chromenes.对映选择性一锅法合成 2-氨基-4-(吲哚-3-基)-4H-色烯。
Org Lett. 2011 Sep 16;13(18):4910-3. doi: 10.1021/ol2019949. Epub 2011 Aug 22.
5
Catalytic asymmetric addition of Meldrum's acid, malononitrile, and 1,3-dicarbonyls to ortho-quinone methides generated in situ under basic conditions.在碱性条件下,丙二酸亚异丙酯、丙二腈和1,3-二羰基化合物对原位生成的邻醌甲基化物的催化不对称加成反应。
Chemistry. 2015 Apr 13;21(16):6037-41. doi: 10.1002/chem.201500710. Epub 2015 Mar 12.
6
Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β-Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation.接力催化:锰(III)磷酸盐催化β-二羰基化合物对通过催化有氧氧化生成的邻醌甲醚的不对称加成。
Org Lett. 2017 Sep 1;19(17):4588-4591. doi: 10.1021/acs.orglett.7b02185. Epub 2017 Aug 15.
7
Copper-catalyzed asymmetric 1,6-conjugate addition of generated -quinone methides with β-ketoesters.铜催化不对称 1,6-共轭加成生成的 -醌甲川与β-酮酯。
Chem Commun (Camb). 2022 Jun 8;58(46):6653-6656. doi: 10.1039/d2cc00146b.
8
C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes.用于对映选择性合成官能化2-氨基-4H-色烯的碳-氢氧化/迈克尔加成/环化串联反应
Org Lett. 2015 Dec 18;17(24):6134-7. doi: 10.1021/acs.orglett.5b03148. Epub 2015 Dec 10.
9
Asymmetric Synthesis of Enantioenriched 2-Aryl-2,3-Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence.通过路易斯酸催化的环丙烷化/分子内重排序列对映体富集的2-芳基-2,3-二氢苯并呋喃进行不对称合成。
Angew Chem Int Ed Engl. 2019 Sep 16;58(38):13427-13432. doi: 10.1002/anie.201906954. Epub 2019 Aug 8.
10
Enantioselective Formal [4 + 2] Annulation of ortho-Quinone Methides with ortho-Hydroxyphenyl α,β-Unsaturated Compounds.邻醌甲基化物与邻羟基苯基α,β-不饱和化合物的对映选择性形式[4 + 2]环化反应
J Org Chem. 2018 Sep 7;83(17):10175-10185. doi: 10.1021/acs.joc.8b01425. Epub 2018 Jul 31.

引用本文的文献

1
One-pot multicomponent green LED photoinduced synthesis of chromeno[4,3-]chromenes catalyzed by a new nanophotocatalyst histaminium tetrachlorozincate.一种新型纳米光催化剂四氯锌酸组胺催化一锅多组分绿色LED光诱导合成色烯并[4,3 - ]色烯类化合物。
RSC Adv. 2021 Jun 1;11(32):19723-19736. doi: 10.1039/d1ra00189b. eCollection 2021 May 27.

本文引用的文献

1
Formal [4 + 2] Annulation of Oxindole-Embedded ortho-Quinone Methides with 1,3-Dicarbonyls: Synthesis of Spiro[Chromen-4,3'-Oxindole] Scaffolds.吲哚并[4,3-b]喹喔啉-2,3-二酮与 1,3-二羰基化合物的[4 + 2]环化反应:螺[色烯-4,3'-吲哚啉]骨架的合成。
J Org Chem. 2019 Apr 5;84(7):3990-3999. doi: 10.1021/acs.joc.8b03260. Epub 2019 Mar 15.
2
Catalytic Asymmetric Hydrophosphination of ortho-Quinone Methides.邻醌甲叉的催化不对称氢膦化反应。
Org Lett. 2018 Nov 16;20(22):7229-7233. doi: 10.1021/acs.orglett.8b03158. Epub 2018 Nov 6.
3
Metal-Catalyzed Oxa-[4+2] Cyclizations of Quinone Methides with Alkynyl Benzyl Alcohols.
金属催化的醌亚甲醚与炔基苄醇的氧杂-[4+2]环化反应。
J Org Chem. 2018 Nov 16;83(22):13861-13873. doi: 10.1021/acs.joc.8b02186. Epub 2018 Nov 1.
4
Application of Naphthylindole-Derived Phosphines as Organocatalysts in [4 + 1] Cyclizations of o-Quinone Methides with Morita-Baylis-Hillman Carbonates.萘基吲哚衍生的膦作为有机催化剂在邻醌甲基化物与森田-贝利斯-希尔曼碳酸酯的[4 + 1]环化反应中的应用。
J Org Chem. 2018 Sep 7;83(17):10060-10069. doi: 10.1021/acs.joc.8b01390. Epub 2018 Aug 23.
5
Enantioselective Formal [4 + 2] Annulation of ortho-Quinone Methides with ortho-Hydroxyphenyl α,β-Unsaturated Compounds.邻醌甲基化物与邻羟基苯基α,β-不饱和化合物的对映选择性形式[4 + 2]环化反应
J Org Chem. 2018 Sep 7;83(17):10175-10185. doi: 10.1021/acs.joc.8b01425. Epub 2018 Jul 31.
6
Recent advances in the application of Diels-Alder reactions involving o-quinodimethanes, aza-o-quinone methides and o-quinone methides in natural product total synthesis.Diels-Alder 反应在天然产物全合成中涉及邻醌二甲烷、氮杂邻醌二甲烷和邻醌二甲烷的应用的最新进展。
Chem Soc Rev. 2018 Oct 29;47(21):7926-7953. doi: 10.1039/c8cs00274f.
7
A chiral scandium-complex-catalyzed asymmetric inverse-electron-demand oxa-Diels-Alder reaction of o-quinone methides with fulvenes.一种手性钪配合物催化的邻醌甲基化物与富烯的不对称逆电子需求氧杂-狄尔斯-阿尔德反应。
Chem Commun (Camb). 2017 Dec 19;54(1):74-77. doi: 10.1039/c7cc08124c.
8
Organocatalytic Phosphonylation of in Situ Formed o-Quinone Methides.有机催化原位生成的邻醌甲亚胺的膦酰化反应。
Org Lett. 2017 Nov 3;19(21):5988-5991. doi: 10.1021/acs.orglett.7b03019.
9
Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho-Quinone Methides and Benzofurans.有机催化的原位生成的乙烯基烯丙基邻醌甲亚胺与苯并呋喃的分子内[4+2]环加成反应。
Angew Chem Int Ed Engl. 2017 Oct 23;56(44):13722-13726. doi: 10.1002/anie.201707523. Epub 2017 Sep 27.
10
Relay Catalysis: Manganese(III) Phosphate Catalyzed Asymmetric Addition of β-Dicarbonyls to ortho-Quinone Methides Generated by Catalytic Aerobic Oxidation.接力催化:锰(III)磷酸盐催化β-二羰基化合物对通过催化有氧氧化生成的邻醌甲醚的不对称加成。
Org Lett. 2017 Sep 1;19(17):4588-4591. doi: 10.1021/acs.orglett.7b02185. Epub 2017 Aug 15.