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通过姜黄素与亚芳基丙二酸酯的共轭加成实现高取代环己酮和四氢色烯-4-酮的非对映选择性合成。

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates.

作者信息

Nair Deepa, Tiwari Abhishek, Laha Banamali, Namboothiri Irishi N N

机构信息

Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400 076, India.

出版信息

Beilstein J Org Chem. 2024 Aug 15;20:2016-2023. doi: 10.3762/bjoc.20.177. eCollection 2024.

DOI:10.3762/bjoc.20.177
PMID:39161707
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11331540/
Abstract

A cascade inter-intramolecular double Michael strategy for the synthesis of highly functionalized cyclohexanones from curcumins and arylidenemalonates is reported. This strategy works in the presence of aqueous KOH using TBAB as a suitable phase transfer catalyst at room temperature. The functionalized cyclohexanones are formed as major products in moderate to excellent yields with complete diastereoselectivity in most cases. A triple Michael adduct, tetrahydrochromen-4-one, is also formed as a side product in a few cases with excellent diastereoselectivity.

摘要

报道了一种从姜黄素和芳亚甲基丙二酸酯合成高度官能化环己酮的级联分子间-分子内双迈克尔策略。该策略在室温下使用四丁基溴化铵作为合适的相转移催化剂，在氢氧化钾水溶液存在下有效。官能化环己酮作为主要产物以中等至优异的产率形成，在大多数情况下具有完全的非对映选择性。在少数情况下，还会形成具有优异非对映选择性的副产物三迈克尔加成物四氢色原酮-4-酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/e481ff7549e2/Beilstein_J_Org_Chem-20-2016-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/137ce55401a9/Beilstein_J_Org_Chem-20-2016-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/bf9834cb2bcf/Beilstein_J_Org_Chem-20-2016-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/d8d618c43a00/Beilstein_J_Org_Chem-20-2016-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/c5921e7540e8/Beilstein_J_Org_Chem-20-2016-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/ff507a87c351/Beilstein_J_Org_Chem-20-2016-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/e481ff7549e2/Beilstein_J_Org_Chem-20-2016-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/137ce55401a9/Beilstein_J_Org_Chem-20-2016-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/bf9834cb2bcf/Beilstein_J_Org_Chem-20-2016-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/d8d618c43a00/Beilstein_J_Org_Chem-20-2016-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/c5921e7540e8/Beilstein_J_Org_Chem-20-2016-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/ff507a87c351/Beilstein_J_Org_Chem-20-2016-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d35/11331540/e481ff7549e2/Beilstein_J_Org_Chem-20-2016-g007.jpg

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本文引用的文献

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Longevity and anti-aging effects of curcumin supplementation.姜黄素补充剂的长寿和抗衰老作用。
Geroscience. 2024 Jun;46(3):2933-2950. doi: 10.1007/s11357-024-01092-5. Epub 2024 Feb 27.
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The Michael donor-acceptor reactivity of curcumins in the synthesis of diverse multi-functional scaffolds.姜黄素在多种多功能支架合成中的迈克尔供体-受体反应活性。
Org Biomol Chem. 2024 Feb 14;22(7):1346-1359. doi: 10.1039/d3ob01734f.
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Regio- and stereoselective synthesis of functionalized tetrahydro-benzochromenes and hexahydrochromenochromenones [4 + 2] annulation of curcumins with nitrochromenes.
具有功能化四氢苯并色烯和六氢色烯色烯酮的区域和立体选择性合成 [4 + 2] 环加成姜黄素与硝色烯。
Org Biomol Chem. 2023 Mar 1;21(9):1872-1877. doi: 10.1039/d2ob02211g.
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Stereoselective synthesis of hydrazinodihydrofurans via cascade Michael addition-substitution involving the reaction of curcumin and other β-dicarbonyls with α-hydrazinonitroalkenes.通过涉及姜黄素和其他β-二羰基化合物与α-氮杂腙硝基烯烃的反应的级联 Michael 加成-取代反应立体选择性合成二氢呋喃肼。
Org Biomol Chem. 2019 Dec 18;18(1):140-153. doi: 10.1039/c9ob01974j.
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A Review of Curcumin and Its Derivatives as Anticancer Agents.姜黄素及其衍生物作为抗癌剂的研究进展。
Int J Mol Sci. 2019 Feb 27;20(5):1033. doi: 10.3390/ijms20051033.
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Immunomodulators Inspired by Nature: A Review on Curcumin and Echinacea.受自然启发的免疫调节剂：姜黄素和紫锥菊的综述。
Molecules. 2018 Oct 26;23(11):2778. doi: 10.3390/molecules23112778.
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Metal complexes of curcumin for cellular imaging, targeting, and photoinduced anticancer activity.姜黄素的金属配合物用于细胞成像、靶向和光诱导抗癌活性。
Acc Chem Res. 2015 Jul 21;48(7):2075-83. doi: 10.1021/acs.accounts.5b00127. Epub 2015 Jul 9.
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