• 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

通过烯丙基醚进行醇官能化一步法通用合成不对称炔丙基缩醛

General one-step access to unsymmetric propargylic acetals alcohol functionalization with allenyl ethers.

作者信息

Long Ai, Li Di, Yan Bo, Yuan Yue, Liu Haoqi, Yang Lan, Chen Yang, He Shuzhong

机构信息

School of Pharmaceutical Sciences, Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University Guiyang Guizhou 550025 China

出版信息

RSC Adv. 2025 Apr 15;15(15):11770-11773. doi: 10.1039/d5ra01533b. eCollection 2025 Apr 9.

DOI:10.1039/d5ra01533b
PMID:40236580
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11997750/
Abstract

We report a straightforward and robust protocol for synthesizing unsymmetric propargylic acetals through single-step alkoxypropargylation of aliphatic alcohols. This method employs allenyl ethers and hypervalent iodine reagents to achieve direct functionalization under mild conditions, producing 26 distinct acetals in 60-94% yields. The reaction's broad substrate compatibility accommodates diverse hydroxyl-containing molecules, offering a versatile and scalable platform for installing alkynyl moieties in complex molecular architectures.

摘要

我们报道了一种通过脂肪醇的单步烷氧基炔丙基化反应合成不对称炔丙基缩醛的简单且稳健的方法。该方法使用烯丙基醚和高价碘试剂在温和条件下实现直接官能团化，以60 - 94%的产率生成26种不同的缩醛。该反应广泛的底物兼容性适用于多种含羟基分子，为在复杂分子结构中引入炔基部分提供了一个通用且可扩展的平台。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/d22b89a0ce01/d5ra01533b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/fe9e8d19ca7f/d5ra01533b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/509bf8039000/d5ra01533b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/d210e03bda72/d5ra01533b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/356e0ece0f66/d5ra01533b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/d22b89a0ce01/d5ra01533b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/fe9e8d19ca7f/d5ra01533b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/509bf8039000/d5ra01533b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/d210e03bda72/d5ra01533b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/356e0ece0f66/d5ra01533b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab9d/11997750/d22b89a0ce01/d5ra01533b-s5.jpg

相似文献

1
General one-step access to unsymmetric propargylic acetals alcohol functionalization with allenyl ethers.通过烯丙基醚进行醇官能化一步法通用合成不对称炔丙基缩醛
RSC Adv. 2025 Apr 15;15(15):11770-11773. doi: 10.1039/d5ra01533b. eCollection 2025 Apr 9.
2
Synthesis of Allenyl-Bdan via the Cu(I)-Catalyzed Borylation of Propargylic Alcohols with the Unsymmetric Diboron Reagent (Bpin-Bdan).通过铜（I）催化的炔丙醇与不对称二硼试剂（Bpin-Bdan）的硼氢化反应合成烯丙基-Bdan。
J Org Chem. 2020 Feb 21;85(4):2823-2831. doi: 10.1021/acs.joc.9b03319. Epub 2020 Jan 22.
3
Hydride-Abstraction-Initiated Catalytic Stereoselective Intermolecular Bond-Forming Processes.氢化物消除引发的催化立体选择性分子间成键过程。
Acc Chem Res. 2022 Dec 6;55(23):3537-3550. doi: 10.1021/acs.accounts.2c00638. Epub 2022 Nov 17.
4
Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts.碱介导脂肪醇与不对称二芳基碘鎓盐反应合成烷基芳基醚
J Org Chem. 2015 Jun 19;80(12):6456-66. doi: 10.1021/acs.joc.5b00907. Epub 2015 Jun 9.
5
Zinc-mediated formation of trifluoromethyl ethers from alcohols and hypervalent iodine trifluoromethylation reagents.锌介导的由醇类和高价碘三氟甲基化试剂形成三氟甲基醚的反应。
Angew Chem Int Ed Engl. 2009;48(24):4332-6. doi: 10.1002/anie.200900974.
6
Adaptive alcohols-alcohols cross-coupling via TFA catalysis: access of unsymmetrical ethers.通过三氟乙酸催化的适应性醇-醇交叉偶联：不对称醚的合成
BMC Chem. 2025 Jan 12;19(1):13. doi: 10.1186/s13065-025-01379-4.
7
Reductive coupling of allenyl/allyl carbonate with alkyne under dual cobalt-photoredox catalysis.双钴-光氧化还原催化下烯丙基/烯丙基碳酸酯与炔烃的还原偶联反应
Nat Commun. 2024 Nov 29;15(1):10421. doi: 10.1038/s41467-024-54718-9.
8
An Organometallic Umpolung Approach for Iron-Mediated Propargylic C-H Etherification.一种用于铁介导的炔丙基C-H醚化反应的有机金属极性反转方法。
Angew Chem Int Ed Engl. 2024 Dec 20;63(52):e202413017. doi: 10.1002/anie.202413017. Epub 2024 Nov 20.
9
A General Access to Propargylic Ethers through Brønsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates .通过三氟硼酸盐催化缩醛和缩酮与炔的亲核加成反应，实现丙炔醚的普遍合成方法。
Chemistry. 2015 Sep 21;21(39):13535-8. doi: 10.1002/chem.201502797. Epub 2015 Aug 6.
10
Synthesis of Benzyl-, Allyl-, and Allenyl-boronates via Copper-Catalyzed Borylation of Alcohols.醇的铜催化硼化合成苄基、烯丙基和炔丙基硼酸酯。
Org Lett. 2017 Mar 3;19(5):1204-1207. doi: 10.1021/acs.orglett.7b00256. Epub 2017 Feb 16.

本文引用的文献

1
Divergent Synthesis of Scabrolide A and Havellockate via an -- Radical Cascade.通过自由基串联反应实现Scabrolide A和Havellockate的发散性合成。
J Am Chem Soc. 2024 May 29;146(21):14422-14426. doi: 10.1021/jacs.4c03995. Epub 2024 May 6.
2
Blue light photoredox-catalysed acetalation of alkynyl bromides.蓝光光氧化还原催化的炔基溴的缩醛化反应
RSC Adv. 2019 Nov 6;9(62):36213-36216. doi: 10.1039/c9ra06596b. eCollection 2019 Nov 4.
3
Total Synthesis of (-)-Indoxamycins A and B.(-)-Indoxamycins A 和 B 的全合成。
Angew Chem Int Ed Engl. 2019 May 13;58(20):6659-6662. doi: 10.1002/anie.201902043. Epub 2019 Apr 4.
4
Discovery of Cell-Permeable O-GlcNAc Transferase Inhibitors via Tethering in Situ Click Chemistry.通过原位连接点击化学发现细胞可渗透的O-连接N-乙酰葡糖胺转移酶抑制剂
J Med Chem. 2017 Jan 12;60(1):263-272. doi: 10.1021/acs.jmedchem.6b01237. Epub 2016 Dec 29.
5
CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: a general method for the synthesis of unsymmetrical propargylic acetals.碘化亚铜催化末端炔烃与二烷氧基卡宾的交叉偶联反应：一种合成不对称炔丙基缩醛的通用方法。
Org Biomol Chem. 2014 Aug 28;12(32):6215-22. doi: 10.1039/c4ob00614c.
6
An approach to cyclohepta[b]indoles through an allenamide (4 + 3) cycloaddition-Grignard cyclization-Chugaev elimination sequence.通过烯酰胺（4 + 3）环加成-格氏环化-楚加耶夫消除序列合成环庚[b]吲哚的方法。
Org Lett. 2014 Apr 18;16(8):2180-3. doi: 10.1021/ol5006455. Epub 2014 Apr 4.
7
Synthesis and SAR of benzamidine factor Xa inhibitors containing a vicinally-substituted heterocyclic core.含邻位取代杂环核心的苯甲脒类凝血因子Xa抑制剂的合成与构效关系
Bioorg Med Chem Lett. 2001 Mar 12;11(5):641-5. doi: 10.1016/s0960-894x(01)00029-4.