• 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

由丙二酸二乙酯或β-溴-α-羟基亚氨基甲酸乙酯制备的非天然α-氨基乙酯。

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate.

作者信息

Coutant Eloi P, Hervin Vincent, Gagnot Glwadys, Ford Candice, Baatallah Racha, Janin Yves L

机构信息

Unité de Chimie et Biocatalyse, Département de Biologie Structurale et Chimie, Institut Pasteur, 28 rue du Dr. Roux, 75724 Paris Cedex 15, France.

Unité Mixte de Recherche 3523, Centre National de la Recherche Scientifique, 28 rue du Dr. Roux, 75724 Paris Cedex 15, France.

出版信息

Beilstein J Org Chem. 2018 Nov 16;14:2853-2860. doi: 10.3762/bjoc.14.264. eCollection 2018.

DOI:10.3762/bjoc.14.264
PMID:30498536
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6244313/
Abstract

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.

摘要

我们在此探索了基于丙二酸二乙酯的古老方法制备α-氨基酯的范围，该方法涉及丙二酸二乙酯与醛的Knoevenagel缩合反应、所得亚烷基丙二酸酯的还原反应、相应α-羟基亚氨基酯的制备及其最终还原反应。尽管遇到了一些意外的限制，但这条合成途径被证明具有通用性。在进行肟化步骤之前，对一些中间体进行合成修饰——使用铃木-宫浦偶联反应或环加成反应——为制备更多α-氨基酯提供了途径。此外，还探索了其他制备α-羟基亚氨基酯的途径，包括尝试改进β-溴-α-羟基亚氨基羧酸乙酯与各种烷基呋喃之间的环加成反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/b1d38fa13839/Beilstein_J_Org_Chem-14-2853-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/9e33f18dcc0a/Beilstein_J_Org_Chem-14-2853-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/3364c8d718f1/Beilstein_J_Org_Chem-14-2853-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/3ab1decc5402/Beilstein_J_Org_Chem-14-2853-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/ad8a4f89959d/Beilstein_J_Org_Chem-14-2853-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/b1d38fa13839/Beilstein_J_Org_Chem-14-2853-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/9e33f18dcc0a/Beilstein_J_Org_Chem-14-2853-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/3364c8d718f1/Beilstein_J_Org_Chem-14-2853-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/3ab1decc5402/Beilstein_J_Org_Chem-14-2853-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/ad8a4f89959d/Beilstein_J_Org_Chem-14-2853-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/6244313/b1d38fa13839/Beilstein_J_Org_Chem-14-2853-g006.jpg

相似文献

1
Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate.由丙二酸二乙酯或β-溴-α-羟基亚氨基甲酸乙酯制备的非天然α-氨基乙酯。
Beilstein J Org Chem. 2018 Nov 16;14:2853-2860. doi: 10.3762/bjoc.14.264. eCollection 2018.
2
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions.使用硝基乙酸乙酯并通过缩合或环加成反应合成非天然α-氨基酸酯。
Beilstein J Org Chem. 2018 Nov 15;14:2846-2852. doi: 10.3762/bjoc.14.263. eCollection 2018.
3
Rational Design of an Iron-Based Catalyst for Suzuki-Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles.基于铁的催化剂用于涉及杂芳基硼酸酯和叔烷基亲电试剂的铃木-宫浦交叉偶联反应的合理设计。
Angew Chem Int Ed Engl. 2020 Mar 23;59(13):5392-5397. doi: 10.1002/anie.201914315. Epub 2020 Feb 25.
4
Catalytic Asymmetric Reactions with -Metallated Azomethine Ylides.手性催化不对称反应与 -金属化亚胺叶立德。
Acc Chem Res. 2020 May 19;53(5):1084-1100. doi: 10.1021/acs.accounts.0c00113. Epub 2020 Apr 22.
5
Stereoselective enol tosylation: preparation of trisubstituted alpha,beta-unsaturated esters.立体选择性烯醇对甲苯磺酰化：三取代α,β-不饱和酯的制备
Org Lett. 2005 Jan 20;7(2):215-8. doi: 10.1021/ol047854z.
6
Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters.钯催化的五氟苯基酯的铃木-宫浦交叉偶联反应。
Molecules. 2018 Nov 29;23(12):3134. doi: 10.3390/molecules23123134.
7
High yielding synthesis of N-ethyl dehydroamino acids.高产合成 N-乙基脱氢氨基酸。
Amino Acids. 2012 Oct;43(4):1643-52. doi: 10.1007/s00726-012-1240-z. Epub 2012 Feb 15.
8
Synthesis of 1-Amino-1H-Indenes via a Sequential Suzuki-Miyaura Coupling/Petasis Condensation Sequence.通过Suzuki-Miyaura 偶联/Petasis 缩合序列合成 1-氨基-1H-茚。
J Org Chem. 2017 Feb 3;82(3):1803-1811. doi: 10.1021/acs.joc.6b02549. Epub 2017 Jan 23.
9
Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: synthesis of 2-aroylbenzoate derivatives.羰基Suzuki-Miyaura 偶联反应：空间位阻芳基卤代物的合成。
Org Biomol Chem. 2020 Mar 4;18(9):1754-1759. doi: 10.1039/d0ob00044b.
10
One-step preparation of enantiopure L- or D-amino acid benzyl esters avoiding the use of banned solvents.避免使用禁用溶剂一步法制备对映体纯的L-或D-氨基酸苄酯
Amino Acids. 2017 May;49(5):965-974. doi: 10.1007/s00726-017-2400-y. Epub 2017 Mar 3.

引用本文的文献

1
Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications.用于DNA编码化学库应用的基于根岸偶联反应合成α-杂芳基-α-氨基酸构建单元
Beilstein J Org Chem. 2024 Aug 8;20:1922-1932. doi: 10.3762/bjoc.20.168. eCollection 2024.
2
Synthetic Chameleon Turns into Oximes, Nitrones, and Hydroxylamines when Exposed to Blue Light.合成变色龙在蓝光照射下会转化为肟、硝酮和羟胺。
ACS Omega. 2024 Mar 14;9(12):14262-14268. doi: 10.1021/acsomega.3c10041. eCollection 2024 Mar 26.
3
Catalyst-Free Transfer Hydrogenation of Activated Alkenes Exploiting Isopropanol as the Sole and Traceless Reductant.

本文引用的文献

1
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions.使用硝基乙酸乙酯并通过缩合或环加成反应合成非天然α-氨基酸酯。
Beilstein J Org Chem. 2018 Nov 15;14:2846-2852. doi: 10.3762/bjoc.14.263. eCollection 2018.
2
Synthetic Routes to Coelenterazine and Other Imidazo[1,2-a]pyrazin-3-one Luciferins: Essential Tools for Bioluminescence-Based Investigations.腔肠素及其他咪唑并[1,2-a]吡嗪-3-酮荧光素的合成路线：基于生物发光研究的重要工具。
Chemistry. 2015 Nov 23;21(48):17158-71. doi: 10.1002/chem.201501531. Epub 2015 Sep 25.
3
Improved Julia-Kocienski conditions for the methylenation of aldehydes and ketones.
利用异丙醇作为唯一无痕还原剂对活性烯烃进行无催化剂转移氢化反应。
Green Chem. 2023 Jan 21;25(2):746-754. doi: 10.1039/d2gc04315g. Epub 2023 Jan 4.
4
Preparation of mono-substituted malonic acid half oxyesters (SMAHOs).单取代丙二酸半酯（SMAHOs）的制备
Beilstein J Org Chem. 2021 Aug 18;17:2085-2094. doi: 10.3762/bjoc.17.135. eCollection 2021.
5
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions.使用硝基乙酸乙酯并通过缩合或环加成反应合成非天然α-氨基酸酯。
Beilstein J Org Chem. 2018 Nov 15;14:2846-2852. doi: 10.3762/bjoc.14.263. eCollection 2018.
用于醛和酮亚甲基化的改进的Julia-Kocienski条件。
J Org Chem. 2006 Jan 6;71(1):360-3. doi: 10.1021/jo051693a.
4
An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem "Pincer" Diels-Alder Reaction.利用串联“钳形”狄尔斯-阿尔德反应立体选择性构建桥连多杂环体系的便捷方法。
J Org Chem. 1997 Jun 27;62(13):4418-4427. doi: 10.1021/jo9701593.
5
Generation, Microwave Spectrum, and Ab Initio MO Calculation of trans-1-Nitrosopropene, CH3CH&dbond;CH-NO (syn form).反式-1-亚硝基丙烯（CH3CH&dbond;CH-NO，顺式结构）的生成、微波光谱及从头算分子轨道计算
J Mol Spectrosc. 1999 Mar;194(1):79-86. doi: 10.1006/jmsp.1998.7774.
6
[On the ingredients of the green amanita. 28. Syntheses of beta-methyl-gamma-hydroxy-leucine and beta-methyl-gamma-delta dihydroxy-leucine, two assumed amantine-elements].[关于绿蝇鹅膏菌的成分。28. β-甲基-γ-羟基亮氨酸和β-甲基-γ,δ-二羟基亮氨酸的合成，两种假定的鹅膏氨酸成分]
Justus Liebigs Ann Chem. 1966 Dec;700:133-48. doi: 10.1002/jlac.19667000117.
7
Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis.二苯基磷酰叠氮化物。一种用于改良库尔提斯反应和肽合成的新型便捷试剂。
J Am Chem Soc. 1972 Aug 23;94(17):6203-5. doi: 10.1021/ja00772a052.
8
Amino acids and peptides. XII. Phosphorus in organic synthesis. VIII. Reaction of malonic acid half esters with diphenyl phosphorazidate.氨基酸与肽。十二。有机合成中的磷。八。丙二酸半酯与二苯基磷酰叠氮化物的反应。
Chem Pharm Bull (Tokyo). 1974 Jun;22(6):1398-404. doi: 10.1248/cpb.22.1398.