Journal of Organic Chemistry最新文献_第2页

Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02320

Suman K. Saha, Anupriya Bera, Akanksha Kumari, Khyati Shukla, Nirmal K. Rana

引用次数: 0

Formal Dearomative Hydroamination of 2-Arylphenols

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02654

Robert E. Wiley, Michael C. Eng, Aidan J. Clarkson, Jeffrey S. Johnson

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Copper-Catalyzed Regioselective Annulation of β-Keto Esters and Propargyl Acetates: Access to Polysubstituted Furans

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02408

Yuchen Yang, Hongke Xu, Fei Li, Yuzhu Yang

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Synthesis and Properties of Thermostable Energetic Benzotriazines 热稳定性高能苯并三嗪的合成及其特性

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02292

Chunhui Chen, Mingjie Tang, Zhiwei Zeng, Yuji Liu, Wei Huang, Yongxing Tang

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Cobalt-Catalyzed Regioselective C8-H Sulfoxamination of 1-Naphthylamine Derivatives with NH-Sulfoximines. 钴催化的 1-萘胺衍生物与 NH-亚磺酰亚胺的 Regioselective C8-H Sulfoxamination。

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 Epub Date: 2024-11-18 DOI: 10.1021/acs.joc.4c02318

Nileshkumar B Rathod, Raj N Patel, Sachinkumar D Patel, Dharmik M Patel, Mahesh A Sonawane, Dinesh Gopichand Thakur, Subhash Chandra Ghosh

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Synthesis, Reactivity and Aromatic Characteristics of Porphyrinoids Derived from N-Alkylcarbaporphyrin-2-Carbaldehydes: Isolation of Nickel(II) and Palladium(II) Complexes, Weakly Diatropic 21-Oxycarbaporphyrins and Strongly Aromatic Trioxycarbaporphyrins

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02145

Kimberly Le, Deyaa I. AbuSalim, Timothy D. Lash

{"title":"Synthesis, Reactivity and Aromatic Characteristics of Porphyrinoids Derived from N-Alkylcarbaporphyrin-2-Carbaldehydes: Isolation of Nickel(II) and Palladium(II) Complexes, Weakly Diatropic 21-Oxycarbaporphyrins and Strongly Aromatic Trioxycarbaporphyrins","authors":"Kimberly Le, Deyaa I. AbuSalim, Timothy D. Lash","doi":"10.1021/acs.joc.4c02145","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02145","url":null,"abstract":"Acid catalyzed condensation of N-alkyltripyrranes with trialdehydes derived from 1,3-cyclopentadiene or methyl-1,3-cyclopentadiene, followed by oxidation with aqueous ferric chloride solutions, gave 23-alkyl-21-carbaporphyrin-2-carbaldehydes in 22–27% yield together with weakly aromatic oxycarbaporphyrins. The carbaporphyrins reacted with palladium(II) acetate or nickel(II) acetate to give organometallic complexes but in both cases alkyl group migration took place to generate 21-alkyl derivatives. Although this type of reactivity had been observed previously for palladium complexes, this is the first time the phenomenon has been seen in nickel(II) carbaporphyrins. Reactions with nickel(II) acetate in refluxing DMF for longer time periods primarily led to decomposition but unusual byproducts were identified. These could be obtained in higher yields by reacting the carbaporphyrin aldehydes with 5 equiv of (bis(trifluoroacetoxy)iodo)benzene in the presence of grade 3 alumina. Decarbonylation and oxidation generate a trioxocyclopentane moiety that is embedded in the porphyrinoid macrocycle. The new system has strongly aromatic properties that are evident from the proton NMR spectra, nucleus independent chemical shift (NICS) calculations and anisotropy of induced ring current plots.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857749","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Generation and Application of All Possible Conformations of Cyclic Tryptophan within and beyond Post-translational Modification

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02532

Akitomo Kasahara, Ryo Yamada, Tadashi Hyodo, Kentaro Yamaguchi, Yuko Otani, Shimpei Sumimoto, Masahiro Okada, Tomohiko Ohwada

{"title":"Generation and Application of All Possible Conformations of Cyclic Tryptophan within and beyond Post-translational Modification","authors":"Akitomo Kasahara, Ryo Yamada, Tadashi Hyodo, Kentaro Yamaguchi, Yuko Otani, Shimpei Sumimoto, Masahiro Okada, Tomohiko Ohwada","doi":"10.1021/acs.joc.4c02532","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02532","url":null,"abstract":"Isoprenylation of the indole C3-position of tryptophan accompanied by cyclization (c-Trp) is one of the most attractive post-translational modifications because of C–C bond formation and drastic conformational alteration. As the modification generates two stereoisomers of the 6/5/5-fused ring system and consequently, a mixture of four possible conformations as considered in proline, it is expected to influence the biological activity in Bacillus quorum sensing pheromone ComX containing the c-Trp residue. In this study, the simultaneous control of the amide cis–trans equilibrium and pyrrolidine ring puckering was achieved by utilizing an N-carbamoylated and α-methylated 6/5/5-fused ring system. Furthermore, the conformationally defined tripeptides containing the c-Trp residue were utilized to examine the relationship between the biological activity and the conformation of the ComX pheromone. Several mimics showed high bioactivity, and more biologically active ComX mimics were created to reinforce the CH-π interaction of the c-Trp and the adjacent aromatic residue.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857752","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1021/acs.joc.4c02363

Liang-Chen Ren, Min Wang, Xiao Zha, Yu-Rui Jian, Li-Ren Zhang, Jia-Jing Tan, Bao-Dong Cui, Yun Zhang, Xue-Qing Mou, Yong-Zheng Chen

引用次数: 0

Competing Photocleavage on Boron and at the meso-Position in BODIPY Photocages

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c02226

Ivan Ljubić, Igor Sviben, Vedran Brusar, Katarina Zlatić, Silvije Vdović, Nikola Basarić

{"title":"Competing Photocleavage on Boron and at the meso-Position in BODIPY Photocages","authors":"Ivan Ljubić, Igor Sviben, Vedran Brusar, Katarina Zlatić, Silvije Vdović, Nikola Basarić","doi":"10.1021/acs.joc.4c02226","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02226","url":null,"abstract":"BODIPY photocages (photocleavable protective groups) have stirred interest because they can release biologically active cargo upon visible light excitation. We conducted combined theoretical and experimental investigations on selected BODIPY photocages to elucidate the mechanism of the competing photocleavage at the boron and meso-position. Based on the computations, the former reaction involves elongation of the B–C bond, yielding a tight borenium cation and methyl anion. These ions are intercepted by CH3OH, enabling an efficient proton-coupled electron transfer (PCET) to produce the methane and isolated ether photoproducts. Singlet and triplet excited-state lifetimes were measured in CH3OH and CD3OD to probe the kinetic isotope effects (KIEs). The resulting KIEs are small, implying that the kinetic bottleneck is due to the C–B bond scission rather than the subsequent PCET. The introduction of a methoxy group in the meso-phenoxy substituent redirects the photosubstitution toward the meso-position. The corresponding regiochemistry was explained computationally. On elongating the C–O bonds in the S1 state, it is found that the unproductive conical intersection is encountered much earlier for the alkyl–O bond than for the phenyl–O bond. The current findings are valuable for the rational design of new BODIPY photocages with tailored biological applications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142857755","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

A Protocol for the Synthesis of Organophosphorus(V) Compounds with P–N and P–O Bonds by Umpolung Strategy Using Hydroxymethylphosphine Sulfides

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2024-12-19 DOI: 10.1021/acs.joc.4c01832

Hidetoshi Ohta, Ryosuke Asahara, Ryusei Ikeda, Tateyuki Sakamoto, Minoru Hayashi

引用次数: 0