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高效区域和立体选择性地获得新型氟化 β-氨基环己烷羧酸酯。

Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates.

机构信息

University of Szeged, Institute of Pharmaceutical Chemistry, Szeged, Hungary.

出版信息

Beilstein J Org Chem. 2013 Jun 17;9:1164-9. doi: 10.3762/bjoc.9.130. Print 2013.

DOI:10.3762/bjoc.9.130
PMID:23843909
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3701410/
Abstract

A regio- and stereoselective method has been developed for the synthesis of novel fluorinated 2-aminocyclohexanecarboxylic acid derivatives with the fluorine attached to position 4 of the ring. The synthesis starts from either cis- or trans-β-aminocyclohex-4-enecarboxylic acids and involves regio- and stereoselective transformation of the ring C-C double bond through iodooxazine formation and hydroxylation, followed by hydroxy-fluorine or oxo-fluorine exchange.

摘要

已开发出一种区域和立体选择性方法，用于合成新型氟化 2-氨基环己烷羧酸衍生物，其中氟原子连接在环的 4 位。合成从顺式或反式-β-氨基环己-4-烯羧酸开始，通过碘噁嗪形成和羟化，然后通过羟基-氟或羰基-氟交换，实现环 C-C 双键的区域和立体选择性转化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/e8c8ce187f0d/Beilstein_J_Org_Chem-09-1164-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/7a8d0eef4f34/Beilstein_J_Org_Chem-09-1164-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/4b055d6d723c/Beilstein_J_Org_Chem-09-1164-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/0ebd9c255443/Beilstein_J_Org_Chem-09-1164-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/cef8d9b7f7ea/Beilstein_J_Org_Chem-09-1164-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/68de50cc4573/Beilstein_J_Org_Chem-09-1164-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/6370d5f4904f/Beilstein_J_Org_Chem-09-1164-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/5a8f9448b881/Beilstein_J_Org_Chem-09-1164-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/e8c8ce187f0d/Beilstein_J_Org_Chem-09-1164-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/7a8d0eef4f34/Beilstein_J_Org_Chem-09-1164-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/4b055d6d723c/Beilstein_J_Org_Chem-09-1164-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/0ebd9c255443/Beilstein_J_Org_Chem-09-1164-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/cef8d9b7f7ea/Beilstein_J_Org_Chem-09-1164-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/68de50cc4573/Beilstein_J_Org_Chem-09-1164-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/6370d5f4904f/Beilstein_J_Org_Chem-09-1164-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/5a8f9448b881/Beilstein_J_Org_Chem-09-1164-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f14d/3701410/e8c8ce187f0d/Beilstein_J_Org_Chem-09-1164-g009.jpg

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本文引用的文献

1
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2
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Bioorg Med Chem. 2012 Aug 1;20(15):4716-26. doi: 10.1016/j.bmc.2012.06.006. Epub 2012 Jun 15.
3
3-Fluoro-N-methyl-D-aspartic acid (3F-NMDA) stereoisomers as conformational probes for exploring agonist binding at NMDA receptors.
Beilstein J Org Chem. 2020 Oct 16;16:2562-2575. doi: 10.3762/bjoc.16.208. eCollection 2020.
4
Fluorination of some highly functionalized cycloalkanes: chemoselectivity and substrate dependence.一些高度官能化环烷烃的氟化反应：化学选择性与底物依赖性
Beilstein J Org Chem. 2017 Nov 6;13:2364-2371. doi: 10.3762/bjoc.13.233. eCollection 2017.
5
Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives.外亚甲基环己烷β-氨基酸衍生物的立体和区域选择性合成
Molecules. 2015 Nov 27;20(12):21094-102. doi: 10.3390/molecules201219749.
3-氟-N-甲基-D-天冬氨酸（3F-NMDA）立体异构体作为构象探针，用于探索 NMDA 受体激动剂结合。
Chemistry. 2012 Jul 9;18(28):8813-9. doi: 10.1002/chem.201200071. Epub 2012 Jun 12.
4
Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids.有机碱催化的立体发散合成（R）-和（S）-3-氨基-4,4,4-三氟丁酸。
Chem Commun (Camb). 2012 Apr 28;48(34):4124-6. doi: 10.1039/c2cc30627a. Epub 2012 Mar 19.
5
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6
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Angew Chem Int Ed Engl. 2012 Feb 27;51(9):2208-12. doi: 10.1002/anie.201107702. Epub 2012 Jan 26.
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Org Biomol Chem. 2012 Jan 28;10(4):861-8. doi: 10.1039/c1ob06575k. Epub 2011 Dec 1.
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Chem Soc Rev. 2012 Mar 21;41(6):2135-71. doi: 10.1039/c1cs15241f. Epub 2011 Nov 30.
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Self-association-driven transition of the β-peptidic H12 helix to the H18 helix.β-肽 H12 螺旋向 H18 螺旋的自缔合驱动转变。
Org Biomol Chem. 2012 Jan 14;10(2):255-9. doi: 10.1039/c1ob06627g. Epub 2011 Nov 23.