Formal synthesis of (±)-lycoramine was described. The key reaction features a dearomatization-Zn/AcOH promoted reductive elimination sequence, followed by a chemoselective reduction of the double bond in enone yielding compound 1, a key intermediate in the total synthesis of (±)- lycoramine.
2024 Elsevier Ltd. All rights reserved.
{"title":"Formal synthesis of (±)-Lycoramine via an acidic Dearomatization–Zn/AcOH reductive elimination sequence","authors":"Shan-Shan Chen, Xiao-Yang Bi, Bao-Yu Li, Jia-Jun Sui, Zhao-Nan Cai, Hong-Bo Qin","doi":"10.1016/j.tetlet.2025.155535","DOIUrl":"10.1016/j.tetlet.2025.155535","url":null,"abstract":"<div><div>Formal synthesis of (±)-lycoramine was described. The key reaction features a dearomatization-Zn/AcOH promoted reductive elimination sequence, followed by a chemoselective reduction of the double bond in enone yielding compound 1, a key intermediate in the total synthesis of (±)- lycoramine.</div><div>2024 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155535"},"PeriodicalIF":1.5,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143696656","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-25DOI: 10.1016/j.tetlet.2025.155562
Qing-Peng He, Rong Chi, Zhen-Ang Liu, Huai-Wei Wang
Herein, we have successfully developed an efficient catalytic protocol to proceed the arylation/esterification cascade reaction of aryl carboxylic acids with aromatic boronates. This catalytic methodology was compatible with various substrates and coupling partners well. This catalytic protocol could proceed the late-stage modification of roflumilast precursor, which offered the potential application of developing novel drug molecules.
{"title":"Rh(III)-catalyzed C(sp2)H arylation and esterification cascade reaction of aryl acids with organic boronates","authors":"Qing-Peng He, Rong Chi, Zhen-Ang Liu, Huai-Wei Wang","doi":"10.1016/j.tetlet.2025.155562","DOIUrl":"10.1016/j.tetlet.2025.155562","url":null,"abstract":"<div><div>Herein, we have successfully developed an efficient catalytic protocol to proceed the arylation/esterification cascade reaction of aryl carboxylic acids with aromatic boronates. This catalytic methodology was compatible with various substrates and coupling partners well. This catalytic protocol could proceed the late-stage modification of roflumilast precursor, which offered the potential application of developing novel drug molecules.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155562"},"PeriodicalIF":1.5,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143726033","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-23DOI: 10.1016/j.tetlet.2025.155555
Yi He , Jiajin Wu , Yuting Liu , Fuhao Liu , Qian Che , Guojian Zhang , Wenxue Wang , Tianjiao Zhu , Dehai Li
Chemical investigations of deep-sea derived fungus Cladosporium halotolerans HDN17-72 yield two new compounds, cladosporisteroid D (1) and cladosporimarin A (2), together with two new natural products (3 and 4), and six known compounds (5–10). Their planar structures were elucidated by detailed analysis of NMR and HRESIMS/MS spectroscopic data. Single-crystal X-ray diffraction analyses resolved the absolute configurations of 1. The absolute configuration of 2 was established by comparison of the specific optical rotation and ECD with that predicted by DFT-based quantum chemical calculation. Compound 2 is the first naturally occurring dihydroisocoumarin derivative linked to the furan ring through the C-4 position. The trihydroxybenzoate derivative 4 exhibited potent antioxidant activity in DPPH radical scavenging test, with an IC50 value of 11.48 μM, better than that of the positive control Vitamin C.
{"title":"New sterol and dihydroisocoumarin from the deep-sea derived fungus Cladosporium halotolerans HDN17-72","authors":"Yi He , Jiajin Wu , Yuting Liu , Fuhao Liu , Qian Che , Guojian Zhang , Wenxue Wang , Tianjiao Zhu , Dehai Li","doi":"10.1016/j.tetlet.2025.155555","DOIUrl":"10.1016/j.tetlet.2025.155555","url":null,"abstract":"<div><div>Chemical investigations of deep-sea derived fungus <em>Cladosporium halotolerans</em> HDN17-72 yield two new compounds, cladosporisteroid D (<strong>1</strong>) and cladosporimarin A (<strong>2</strong>), together with two new natural products (<strong>3</strong> and <strong>4</strong>), and six known compounds (<strong>5</strong>–<strong>10</strong>). Their planar structures were elucidated by detailed analysis of NMR and HRESIMS/MS spectroscopic data. Single-crystal X-ray diffraction analyses resolved the absolute configurations of <strong>1</strong>. The absolute configuration of <strong>2</strong> was established by comparison of the specific optical rotation and ECD with that predicted by DFT-based quantum chemical calculation. Compound <strong>2</strong> is the first naturally occurring dihydroisocoumarin derivative linked to the furan ring through the C-4 position. The trihydroxybenzoate derivative <strong>4</strong> exhibited potent antioxidant activity in DPPH radical scavenging test, with an IC<sub>50</sub> value of 11.48 <em>μ</em>M, better than that of the positive control Vitamin C.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155555"},"PeriodicalIF":1.5,"publicationDate":"2025-03-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143704727","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-22DOI: 10.1016/j.tetlet.2025.155548
Ayon Sengupta , Chhanda Mukhopadhyay
In view of the versatility of the Petasis reaction (PR) for the synthesis of different organic compounds with enormous applications in biology and pharmaceutics, this short review is intended to focus on the Petasis and associated reactions that produces multiple (more than one) stereogenic centres. The reactions were organised and categorized on the basis of the number of stereocenters centres generated in the overall process. The multicomponent reactions with dual PR sequences, asymmetric PRs, and build/couple/pair (B/C/P) strategies involving PR/IMDA(intramolecular Diels–Alder)/RCM(ring-closing metathesis)/ROM(ring-opening metathesis) cascades were captured in this review.
{"title":"Petasis reaction: An expeditious generation of multiple stereogenic centres","authors":"Ayon Sengupta , Chhanda Mukhopadhyay","doi":"10.1016/j.tetlet.2025.155548","DOIUrl":"10.1016/j.tetlet.2025.155548","url":null,"abstract":"<div><div>In view of the versatility of the Petasis reaction (PR) for the synthesis of different organic compounds with enormous applications in biology and pharmaceutics, this short review is intended to focus on the Petasis and associated reactions that produces multiple (more than one) stereogenic centres. The reactions were organised and categorized on the basis of the number of stereocenters centres generated in the overall process. The multicomponent reactions with dual PR sequences, asymmetric PRs, and build/couple/pair (B/C/P) strategies involving PR/IMDA(intramolecular Diels–Alder)/RCM(ring-closing metathesis)/ROM(ring-opening metathesis) cascades were captured in this review.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155548"},"PeriodicalIF":1.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714902","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-22DOI: 10.1016/j.tetlet.2025.155556
Shan-Shan Chen , Li Wang , Yi-Nong Wang , Bang-Yin Tan , Chang-Bin Wang , Yu Duan , Yun-Li Zhao , Xiao-Dong Luo
Toddamarin A, a new prenylated coumarin dimer with a new type of 1,3,4,4,5-pentasubstituted cyclohexene ring was isolated from the roots of Toddalia asiatica. Notably, it possessed both chiral centers and stereogenic axes, exhibiting atropisomeric property as evidenced by ROESY and variable temperature NMR experiment. Additionally, a plausible biosynthetic pathway was proposed. The finding enriched the chemical diversity of coumarins, and provided promising molecular template for stereoselective synthesis.
{"title":"Toddamarin A, a rare atropisomeric biscoumarin with multi-axis from Toddalia asiatica","authors":"Shan-Shan Chen , Li Wang , Yi-Nong Wang , Bang-Yin Tan , Chang-Bin Wang , Yu Duan , Yun-Li Zhao , Xiao-Dong Luo","doi":"10.1016/j.tetlet.2025.155556","DOIUrl":"10.1016/j.tetlet.2025.155556","url":null,"abstract":"<div><div>Toddamarin A, a new prenylated coumarin dimer with a new type of 1,3,4,4,5-pentasubstituted cyclohexene ring was isolated from the roots of <em>Toddalia asiatica</em>. Notably, it possessed both chiral centers and stereogenic axes, exhibiting atropisomeric property as evidenced by ROESY and variable temperature NMR experiment. Additionally, a plausible biosynthetic pathway was proposed. The finding enriched the chemical diversity of coumarins<em>,</em> and provided promising molecular template for stereoselective synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155556"},"PeriodicalIF":1.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-22DOI: 10.1016/j.tetlet.2025.155546
Jason Y. Wang , Flora Fan , Madeline E. Ruos , Leticia Adao Gomes , Mimi Lavin , Thomas J. O'Connor , Steven A. Lopez , Abigail G. Doyle
Herein, we describe the discovery and characterization of multiple N-(hetero)aryl, N-benzyl and N-alkyl derivatives of 9-mesityl-3,6-di-tert-butyl-10-phenyl acridinium photocatalyst. The catalytic performances of these catalysts as photo-oxidant or photo-reductant (via in situ generated acridine radical) were compared in three model reactions. We also identified improved catalytic conditions for a previous cyanoarene-catalyzed nucleophilic amination reaction using a synthesized N-cycloheptyl acridinium catalyst (up to 98 % yield).
{"title":"Diversification of acridinium photocatalysts: Property tuning and reactivity in model reactions","authors":"Jason Y. Wang , Flora Fan , Madeline E. Ruos , Leticia Adao Gomes , Mimi Lavin , Thomas J. O'Connor , Steven A. Lopez , Abigail G. Doyle","doi":"10.1016/j.tetlet.2025.155546","DOIUrl":"10.1016/j.tetlet.2025.155546","url":null,"abstract":"<div><div>Herein, we describe the discovery and characterization of multiple <em>N</em>-(hetero)aryl, <em>N</em>-benzyl and <em>N</em>-alkyl derivatives of 9-mesityl-3,6-di-<em>tert</em>-butyl-10-phenyl acridinium photocatalyst. The catalytic performances of these catalysts as photo-oxidant or photo-reductant (via <em>in situ</em> generated acridine radical) were compared in three model reactions. We also identified improved catalytic conditions for a previous cyanoarene-catalyzed nucleophilic amination reaction using a synthesized <em>N</em>-cycloheptyl acridinium catalyst (up to 98 % yield).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155546"},"PeriodicalIF":1.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143682059","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-21DOI: 10.1016/j.tetlet.2025.155553
Junyi Zheng , Siyi Li , Shunpeng Bai , Xiao Liu , Ruitao Sun , Shengzhen Xu , Wei Qu
In this study, a novel two-photon fluorescent probe, ZT1, leveraging the photoinduced electron transfer (PET) effect was designed and synthesized. The probe employs 4-trifluoromethyl coumarin as the fluorophore and 2,2′-dipicolylamine (DPA) as the Zn2+ recognition group, enabling non-destructive detection of Zn2+ in Arabidopsis thaliana. ZT1 demonstrated exceptional selectivity for Zn2+ in both in vitro and in vivo assays, maintained stability across a pH range of 6–8, featured a detection limit as low as 13.96 nM, and exhibited a large Stokes shift (177 nm). The probe facilitated high-resolution visualization of Zn2+ in the root tips and leaf tissues of Arabidopsis thaliana and demonstrated remarkable reversibility in cyclic experiments. This work establishes a robust toolkit that overcomes longstanding limitations in plant metal ion imaging, offering mechanistic insights into zinc-regulated physiological processes.
{"title":"An organic small molecule fluorescent probe for nondestructive detection of Zn2+ in plants","authors":"Junyi Zheng , Siyi Li , Shunpeng Bai , Xiao Liu , Ruitao Sun , Shengzhen Xu , Wei Qu","doi":"10.1016/j.tetlet.2025.155553","DOIUrl":"10.1016/j.tetlet.2025.155553","url":null,"abstract":"<div><div>In this study, a novel two-photon fluorescent probe, <strong>ZT1</strong>, leveraging the photoinduced electron transfer (PET) effect was designed and synthesized. The probe employs 4-trifluoromethyl coumarin as the fluorophore and 2,2′-dipicolylamine (DPA) as the Zn<sup>2+</sup> recognition group, enabling non-destructive detection of Zn<sup>2+</sup> in <em>Arabidopsis thaliana</em>. <strong>ZT1</strong> demonstrated exceptional selectivity for Zn<sup>2+</sup> in both <em>in vitro</em> and <em>in vivo</em> assays, maintained stability across a pH range of 6–8, featured a detection limit as low as 13.96 nM, and exhibited a large Stokes shift (177 nm). The probe facilitated high-resolution visualization of Zn<sup>2+</sup> in the root tips and leaf tissues of <em>Arabidopsis thaliana</em> and demonstrated remarkable reversibility in cyclic experiments. This work establishes a robust toolkit that overcomes longstanding limitations in plant metal ion imaging, offering mechanistic insights into zinc-regulated physiological processes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155553"},"PeriodicalIF":1.5,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776698","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A key intermediate in the enantioselective synthesis of (+)-neovibsanins A and B was synthesized from (E)-geranic acid in only six steps. Strategic asymmetric 1,4-addition and asymmetric aldol reactions were used to construct successive chiral centers adjacent to a chiral tetraalkylated (all‑carbon) quaternary center and ring closing metathesis using Grubbs catalyst, forming the A-ring moiety was effective in reducing the number of steps leading to the key intermediate.
{"title":"Improved approach to the enantioselective synthesis of (+)-neovibsanins A and B","authors":"Tomoyuki Esumi , Emi Matsuo , Mitsuki Tanahara , Tadashi Hyodo , Kentaro Yamaguchi , Hirofumi Yamamoto , Yoshinori Asakawa","doi":"10.1016/j.tetlet.2025.155552","DOIUrl":"10.1016/j.tetlet.2025.155552","url":null,"abstract":"<div><div>A key intermediate in the enantioselective synthesis of (+)-neovibsanins A and B was synthesized from (<em>E</em>)-geranic acid in only six steps. Strategic asymmetric 1,4-addition and asymmetric aldol reactions were used to construct successive chiral centers adjacent to a chiral tetraalkylated (all‑carbon) quaternary center and ring closing metathesis using Grubbs catalyst, forming the A-ring moiety was effective in reducing the number of steps leading to the key intermediate.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155552"},"PeriodicalIF":1.5,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143785060","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-19DOI: 10.1016/j.tetlet.2025.155529
Chibisree Elanchezhian , Diksha Bansal , Pooja Sivaganesan , Gokulprasanth Nataraj , Mrinal Kanti Das , Saikat Chaudhuri
Benzazepinoindoles are a promising class of compounds in the growing field of heterocyclic chemistry due to their intriguing pharmacological properties. The tetrahydro-benzazepinoindole scaffold, in particular, holds great promise as a versatile framework for drug discovery, especially in the development of antiproliferative and anti-inflammatory agents. In present work, we proposed the synthesis of tetrahydro-benzazepinoindoles starting from alkylated indole and benzaldehyde derivatives using NH4Cl, and methanol as solvent. This approach is designed to achieve high efficiency and good to excellent yields, while accommodating diverse functional groups to enhance structural diversity. The scalability of this method was demonstrated through successful gram-scale reactions, highlighting its utility in practical applications. The synthesized compounds were characterized using advanced techniques, including 1H NMR, 13C NMR, 19F NMR, DEPT-135, IR and mass spectrometry, confirming their structural integrity. This work provides a streamlined and reliable strategy for the synthesis of tetrahydro-benzazepinoindoles, contributing to advancements in synthetic methodology and paving the way for the development of novel bioactive molecules with significant therapeutic potential.
{"title":"A convenient ammonium chloride facilitated mild and efficient synthesis of Benzazepinoindole derivatives through a Pictet-Spengler reaction*","authors":"Chibisree Elanchezhian , Diksha Bansal , Pooja Sivaganesan , Gokulprasanth Nataraj , Mrinal Kanti Das , Saikat Chaudhuri","doi":"10.1016/j.tetlet.2025.155529","DOIUrl":"10.1016/j.tetlet.2025.155529","url":null,"abstract":"<div><div>Benzazepinoindoles are a promising class of compounds in the growing field of heterocyclic chemistry due to their intriguing pharmacological properties. The tetrahydro-benzazepinoindole scaffold, in particular, holds great promise as a versatile framework for drug discovery, especially in the development of antiproliferative and anti-inflammatory agents. In present work, we proposed the synthesis of tetrahydro-benzazepinoindoles starting from alkylated indole and benzaldehyde derivatives using NH<sub>4</sub>Cl, and methanol as solvent. This approach is designed to achieve high efficiency and good to excellent yields, while accommodating diverse functional groups to enhance structural diversity. The scalability of this method was demonstrated through successful gram-scale reactions, highlighting its utility in practical applications. The synthesized compounds were characterized using advanced techniques, including <sup>1</sup>H NMR, <sup>13</sup>C NMR, <sup>19</sup>F NMR, DEPT-135, IR and mass spectrometry, confirming their structural integrity. This work provides a streamlined and reliable strategy for the synthesis of tetrahydro-benzazepinoindoles, contributing to advancements in synthetic methodology and paving the way for the development of novel bioactive molecules with significant therapeutic potential.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155529"},"PeriodicalIF":1.5,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143654773","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-15DOI: 10.1016/j.tetlet.2025.155545
Pritesh Khobrekar , Sandesh Bugde
In this work, we demonstrate the use of rose-bengal derived carbon dots for C-3 thiocyanation of indoles. These carbon dots serve as an non-toxic, biocompatible and environmentally friendly catalysts for the C-3 thiocyanation reaction. To our best knowledge, this is the first report to use rose-bengal derived carbon dots for C-3 thiocyanation of indoles. The yield of the synthesized derivatives of indoles were found to be good to excellent in the range of 33 % to 84 %.
{"title":"Visible-light-induced aerobic C-3 thiocyanation of indoles using carbon dots as photoredox catalyst","authors":"Pritesh Khobrekar , Sandesh Bugde","doi":"10.1016/j.tetlet.2025.155545","DOIUrl":"10.1016/j.tetlet.2025.155545","url":null,"abstract":"<div><div>In this work, we demonstrate the use of rose-bengal derived carbon dots for C-3 thiocyanation of indoles. These carbon dots serve as an non-toxic, biocompatible and environmentally friendly catalysts for the C-3 thiocyanation reaction. To our best knowledge, this is the first report to use rose-bengal derived carbon dots for C-3 thiocyanation of indoles. The yield of the synthesized derivatives of indoles were found to be good to excellent in the range of 33 % to 84 %.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155545"},"PeriodicalIF":1.5,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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