Journal of Organic Chemistry最新文献_第2页

Development of a Carbonyl Cyclopentannulation Reagent Based on a 1,4-Dithiane-Fused Nazarov Reaction 基于1,4-二硫烷熔合Nazarov反应的羰基环戊烷试剂的研制

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c01924

Ellen Demeyere,Kristof Van Hecke,Johan M. Winne

引用次数: 0

Conformational Lability of Bispidine as a Route to New Polycyclic Compounds 比斯必定作为合成新多环化合物途径的构象稳定性

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c01744

Aleksei V. Medved’ko,Sergey Z. Vatsadze

引用次数: 0

Deciphering the Mechanistic Origin of Divergent Radical Annulation Reactions of ortho-Cyanoaryl Acrylamides 正氰基丙烯酰胺歧化自由基环化反应的机理起源

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c01863

Meryem Fıstıkçı,Yunus Zozik,Selçuk Eşsiz

{"title":"Deciphering the Mechanistic Origin of Divergent Radical Annulation Reactions of ortho-Cyanoaryl Acrylamides","authors":"Meryem Fıstıkçı,Yunus Zozik,Selçuk Eşsiz","doi":"10.1021/acs.joc.6c01863","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01863","url":null,"abstract":"The divergent radical annulation reactions of ortho-cyanoaryl acrylamides involving cyanomethyl and α-oxyalkyl radicals were investigated using density functional theory (DFT) combined with DLPNO-CCSD(T) single-point computations. The calculations provide a detailed mechanistic comparison of the experimentally observed reaction pathways and reveal distinct downstream reactivity of the corresponding radical intermediates. Activation strain model (ASM) analyses show that the competing cyclization and C–C bond cleavage via β-scission pathways are characterized by different balances between structural distortion and interfragment interactions. For the cyanomethyl-radical-derived system, the cyclization pathway is associated with a substantially lower distortion energy, whereas for the α-oxyalkyl-radical-derived system, the cleavage pathway benefits from stronger stabilizing interfragment interactions that compensate for the larger distortion penalty. Noncovalent interaction (NCI) analyses provide qualitative structural support for these energetic trends. Overall, these computations provide a detailed mechanistic comparison of the competing downstream pathways of the cyanomethyl- and α-oxyalkyl-radical-derived intermediates.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218951","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

Sodium Borohydride Reduction of Esters in Toluene Using the All-at-Once Addition Method with an Alcohol Activator 溴氢化钠用醇活化剂一次性加成法还原甲苯中的酯类

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c01934

Toshinobu Korenaga,Reito Endo,Mayu Ishida,Mizuki Nakagawa,Yuto Honma

引用次数: 0

Second-Generation Synthesis of the Male Contraceptive YCT-529 第二代男性避孕药YCT-529的合成

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c01804

Naresh Gantasala,Narsihmulu Cheryala,Gunda I. Georg

引用次数: 0

Mechanochemistry-Enabled One-Pot Formation of 1,2,4-Triazoles toward the Sustainable Penipanoid A Synthesis 机械化学一锅法合成1,2,4-三唑类化合物的研究

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c02087

Sachin Balu Chavan,Dipali Rao,Sushila Dilraj Joshi,Mangala Phadte

引用次数: 0

Sequential Relay Catalysis in a Multicomponent [4 + 1] Cycloaddition for the Synthesis of Highly Functionalized Pyrazoles 多组分[4 + 1]环加成序继电催化合成高功能化吡唑

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-20 DOI: 10.1021/acs.joc.6c01662

Qin Luo,Yi-Ting Wang,Meng-Zhen Wei,Zhi-Bo Xie,Cong-Hai Zhang,Sheng-Jiao Yan

{"title":"Sequential Relay Catalysis in a Multicomponent [4 + 1] Cycloaddition for the Synthesis of Highly Functionalized Pyrazoles","authors":"Qin Luo,Yi-Ting Wang,Meng-Zhen Wei,Zhi-Bo Xie,Cong-Hai Zhang,Sheng-Jiao Yan","doi":"10.1021/acs.joc.6c01662","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01662","url":null,"abstract":"We report a Sc(OTf)3/AgOAc relay-catalyzed multicomponent [4 + 1] cycloaddition cascade for the efficient synthesis of polysubstituted pyrazoles 5–6 from sulfoxonium ylides, vinyl diazo esters, and vinylene carbonates or maleimides. Although vinyl diazo esters have been widely used as C1 and three-atom synthons, their application as four-atom (C2N2) building blocks remains underexplored. This bimetallic relay strategy features well-defined and complementary catalytic roles: Sc(III) promotes pyrazole ring assembly, whereas Ag(I) facilitates sequential alkene functionalization while suppressing undesired side reactions. The one-pot cascade proceeds under ambient conditions with excellent step economy, forms three new chemical bonds in a single operation, and affords structurally diverse pyrazoles with good functional-group tolerance. Mechanistic studies support the proposed relay catalytic pathway. The reaction is readily scalable to gram scale, providing a modular and practical approach to the rapid synthesis and late-stage diversification of biologically valuable pyrazole derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218919","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

Visible-Light Photoredox-Catalyzed Sp3 C-H Sulfonylation of Oxime Ester. 可见光光氧化催化肟酯的Sp3 C-H磺化反应。

IF 3.3 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c01729

Zijie Zhang, Yuejie Sun, Jie Huang, Yiqi Yan, Yujie Zhi, Ying Han, Shaoqun Zhu

引用次数: 0

Synthesis of o-Carborane Amides from o-Carborane Carboxylic Acids via Acyloxyphosphonium Ion 酰基氧磷离子催化邻碳硼烷羧酸合成邻碳硼烷酰胺

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c00728

Zi-Teng Yang,Huifen Ma,Shi-Chao Li,Xu Guo,Xinling Wang,Jing Yang,Li-Xin Li

引用次数: 0

Conjugated and Side-Chain Cationic Peptide Nucleic Acids (PNAs): Synthesis and Enhanced Cell Uptake of Cationic PNAs and Their DNA Duplexes into Cells 共轭和侧链阳离子肽核酸（PNAs）：合成和增强阳离子PNAs的细胞摄取及其DNA双链进入细胞

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2026-10-19 DOI: 10.1021/acs.joc.6c01245

Rajat H. Sudarshana,Madhu Ramesh,Ramjayakumar Venkatesh,Krishna N. Ganesh

{"title":"Conjugated and Side-Chain Cationic Peptide Nucleic Acids (PNAs): Synthesis and Enhanced Cell Uptake of Cationic PNAs and Their DNA Duplexes into Cells","authors":"Rajat H. Sudarshana,Madhu Ramesh,Ramjayakumar Venkatesh,Krishna N. Ganesh","doi":"10.1021/acs.joc.6c01245","DOIUrl":"https://doi.org/10.1021/acs.joc.6c01245","url":null,"abstract":"Peptide nucleic acids are neutral analogues of DNA with an aminoethyl glycine polyamide backbone, which renders a higher binding affinity to complementary DNA but reduces cell permeability due to increased hydrophobicity. We have conjugated aeg-PNA with the cationic amino acids lysine (lys), arginine (arg), and the dipeptides lys-lys and arg-arg at the N/C-terminus and introduced cationic S-aminomethylene (S-am) and S-methylene guanidine (S-mgd) side chains at Cα in 8-mer PNAs. The thermal stability of cationic PNA:DNA duplexes was enhanced due to electrostatic interactions between the cationic PNA substitutions and the anionic DNA in the range of 6–11 °C and in the following order: PNA 12-S-am2 >PNA 9-S-mgd >PNA 10-lys2 >PNA 5-S-mgd >PNA 4 S-am)∼PNA 8-arg>PNA 11-arg2, and the rest were < 3.0 °C. The side-chain-modified substitutions were generally better than the end-conjugated amino acids. The single-stranded C-terminus cationic PNAs showed 1.4–1.7-fold higher cell uptake than aeg-PNA in SH-SY5Y cells, in the following order: S-am2>S-mgd >arg2>lys> lys2>arg>S-am>aeg-PNA. FRET experiments of cationic PNA hybridized with fluorescently labeled DNA within cells exhibited increased cellular uptake of PNA:DNA duplexes, with the CF-PNA 12-S-am2 up by 12.7-fold, suggesting significantly improved cell uptake of cationic PNA:DNA duplexes. FRET imaging indicated the uptake of intact cationic PNA:DNA duplexes into the cells, suggesting their application potential for transporting DNA into cells.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"45 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2026-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149218913","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