Journal of Organic Chemistry最新文献_第4页

Rapid Chemical Synthesis of Neuroprotective Hi1a. 神经保护Hi1a的快速化学合成。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-13 DOI: 10.1021/acs.joc.5c01533

Stephen A Byrne,Giulio Fittolani,Elee Shimshoni,Charlotte E Farquhar,Julien Couture-Senécal,Andrei Loas,Daniel G Anderson,Bradley L Pentelute

引用次数: 0

Chemical Synthesis of the Pentasaccharide Related to the Exopolysaccharide of Aeromonas veronii bv. Sobria Strain K49. 维罗氏气单胞菌胞外多糖相关五糖的化学合成索布里亚K49号。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-13 DOI: 10.1021/acs.joc.5c01883

Annesha Dutta,Balaram Mukhopadhyay

引用次数: 0

Synthesis of Indeno-Quinolones and Their Functionalization toward 5-HT3 Receptor. 吲哚诺酮类药物的合成及其对5-HT3受体的功能化。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-13 DOI: 10.1021/acs.joc.5c01433

Kapil Chahal,Vijaya Rani Potluri,Donamol Tomy,Kirti Vashishtha,Kallu Rajender Reddy

引用次数: 0

DFT Insights into the Mechanistic Switch from Carbene to Carbocation in B(C6F5)3-Catalyzed Coupling of Diazooxindoles and Difluoroenoxysilanes in HFIP. B(C6F5)3催化重氮唑啉与二氟烯氧基硅烷在HFIP中从碳正离子到碳正离子的转换机理的DFT研究。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-13 DOI: 10.1021/acs.joc.5c01257

Lizi Yang,Chengze Xin,Ran Fang

引用次数: 0

Investigation into the Stereoelectronics of the Thiol-Promoted Fragmentation of Ylidenenorbornadienes (YNDs). 巯基促进壬基二烯断裂的立体电子学研究。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-12 DOI: 10.1021/acs.joc.5c01885

Quinn E Williams,Scott J L'Heureux,Cameron J Fleischer,Danilo J Alamillo,Ashley N Freeman,Jacob Bellamah,Jono Moore,Joaquin Gonzalez,Erin Ituralde,Scott Borchers,Maya J Frey,Shawn D Larson,Sonia Patil,Jacob D Landa,Gisele P Guerrero,Philip J Costanzo,Daniel A Bercovici

{"title":"Investigation into the Stereoelectronics of the Thiol-Promoted Fragmentation of Ylidenenorbornadienes (YNDs).","authors":"Quinn E Williams,Scott J L'Heureux,Cameron J Fleischer,Danilo J Alamillo,Ashley N Freeman,Jacob Bellamah,Jono Moore,Joaquin Gonzalez,Erin Ituralde,Scott Borchers,Maya J Frey,Shawn D Larson,Sonia Patil,Jacob D Landa,Gisele P Guerrero,Philip J Costanzo,Daniel A Bercovici","doi":"10.1021/acs.joc.5c01885","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01885","url":null,"abstract":"A simplified synthesis of 6,6-diaryl-substituted fulvenes from substituted benzophenones is reported, providing excellent yields for all substrates except those with strong electron-donating substituents. Symmetric diaryl-ylidenenorbornadienes (YNDs) were prepared via the reaction between 6,6-diaryl-substituted fulvenes and dimethyl acetylenedicarboxylate (DMAD). These YNDs were then reacted with propanethiol (PT) to afford four isolable diastereomers of YND-PT adducts, with trends in diastereomer ratios being attributed to the directing capabilities of aryl substituents during thiolate addition and protonation steps. Linear-free energy correlations were obtained for the retro-[4 + 2] fragmentation of substituted diaryl-YND-PTs. Electron-donating groups on the phenyl substituents on the ylidene of YNDs increased fragmentation rates. The half-lives of fragmentation typically increased by approximately 10-fold from the most electron-donating substituent (NMe2) to the most electron-withdrawing (NO2). The individual diastereomers were observed to fragment at markedly different rates. In one substrate, the fastest diastereomer fragmented 100 times faster than the slowest. A series of thiophenols (TPs) were used as the nucleophiles with a model YND system and provided a separable mixture of three diastereomers of YND-TP adducts. Linear-free energy correlations were obtained for the retro-[4 + 2] fragmentation of YND-TPs. Electron-withdrawing substituents on thiophenyl ethers were observed to increase the fragmentation rates of all diastereomers.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"136 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145277276","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

Cobalt-Catalyzed Enantioselective Arylation of Isatin Derivatives with Arylboronic Acids. 钴催化Isatin衍生物与芳基硼酸的对映选择性芳基化。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-12 DOI: 10.1021/acs.joc.5c01349

Xiang Xu,Wenxin Lu,Zhihan Zhang,Xing-Wang Wang,Qinglei Chong,Fanke Meng

引用次数: 0

Short Synthesis of [10]Paracyclophanes from Strained [10]Paracyclopha-4,6-diynes Obtained via a Double Negishi Coupling Followed by an Intramolecular Glaser Cyclization. 由双根石偶联和分子内玻璃环化得到的[10]副环环-4,6-二炔短时间合成[10]副环环。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-12 DOI: 10.1021/acs.joc.5c01567

Yuki Kamata,Tsubasa Sugawara,Hajime Kikkawa,Ririka Hori,Yusuke Miyashita,Nobuhiro Kanomata,Ryutaro Ono,Masaki Kakinuma,Yuki Ono,Yuji Sato,Takumi Kashima,Yamato Kanetaka,Satoshi Maruyama,Hiroki Takizawa

引用次数: 0

Solvent-Mediated C- or N-Center Selective Syn-Hydroheteroarylation of Ynamides with N-Heteroaromatics: Access to a Solvatofluorochromic, Mechanofluorochromic, and Thermochromic Material 溶剂介导的与n-杂芳烃的酰胺的C-或n-中心选择性同步氢杂芳化：获得溶剂荧光变色、机械荧光变色和热变色材料

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c01325

Appanapalli N. V. Satyanarayana, Tanmay Chatterjee

{"title":"Solvent-Mediated C- or N-Center Selective Syn-Hydroheteroarylation of Ynamides with N-Heteroaromatics: Access to a Solvatofluorochromic, Mechanofluorochromic, and Thermochromic Material","authors":"Appanapalli N. V. Satyanarayana, Tanmay Chatterjee","doi":"10.1021/acs.joc.5c01325","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01325","url":null,"abstract":"We report a solvent (HFIP)-mediated, C- or N-center selective, and 100% atom-economic syn-hydroheteroarylation of ynamides with N-heteroaromatics to access a wide variety of stereodefined α-heteroarylenamides at room temperature in good to excellent yield of up to 98%. While indole, pyrrole, and furan underwent the reaction with ynamides via a C-center, other N-heterocycles, such as pyrazole, triazole, and phenothiazine, underwent the same via the N-center, selectively. This chemo-, regio-, and stereoselective transformation required only HFIP, which played a couple of crucial roles, such as Brønsted acid to protonate ynamide regioselectively to generate the reactive keteniminium intermediate and then stabilize the intermediate as an indispensable solvent through H-bonding. Notably, the reactions were very clean, and the products were obtained pure without requiring column chromatography in many cases. HFIP is recovered through distillation (∼90% recovery) and recycled for subsequent reactions without any compromise in the reaction outcome. The green chemistry metrics of this protocol were excellent. Significantly, this green protocol enabled the direct synthesis of highly substituted N-H carbazoles from N-H indoles via a one-pot, two-step strategy by using only a couple of solvents, i.e., HFIP and toluene. Interestingly, a synthesized product, i.e., (Z)-N-(1-(1H-indol-3-yl)-2-(4-nitrophenyl)vinyl)-N-benzylbenzenesulfonamide, exhibited interesting properties, such as solvatofluorochromism, mechanofluorochromism, and reversible thermochromism.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261487","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

Rapid Discovery of Guaiane-Type Sesquiterpenoids with Rare Ring Skeletons from Daphne aurantiaca using Molecular Networking Together with MS-DIAL and Self-Built Database 利用分子网络、MS-DIAL和自建数据库快速发现金牡丹稀有环骨架的瓜蓝型倍半萜类化合物

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c01969

Shu-Hui Dong, Zhi-Kang Duan, Mei-Ya Lian, Ming Bai, Xiao-Xiao Huang, Shao-Jiang Song

{"title":"Rapid Discovery of Guaiane-Type Sesquiterpenoids with Rare Ring Skeletons from Daphne aurantiaca using Molecular Networking Together with MS-DIAL and Self-Built Database","authors":"Shu-Hui Dong, Zhi-Kang Duan, Mei-Ya Lian, Ming Bai, Xiao-Xiao Huang, Shao-Jiang Song","doi":"10.1021/acs.joc.5c01969","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01969","url":null,"abstract":"Under the guidance of the approach that integrates molecular networking, MS-DIAL and self-built database, 11 undescribed guaiane-type sesquiterpenoids (1–11) along with four known analogs (12–15) were targeted and isolated from Daphne aurantiaca. Among these, dapurant A–B (1–2) were unusual guaiane-type sesquiterpenoid dimers consisting of two guaiane-type sesquiterpenoids with different ring skeletons, and dapurant C–D (3–4) represented rare chlorinated guaiacane-type sesquiterpenoids. Their chemical structures and configurations were established via NMR spectroscopy analysis, computer-assisted structure elucidation methods, density functional theory (DFT) NMR calculations with suitable analysis methods (custom DP4+ analysis, CP3 analysis, MAEΔΔδ), DU8+, electron-capture detector, detection (EC)D calculations, Rh2(OCOCF3)4-induced ECD analysis along with semisynthesis method. The network pharmacology analysis prompted us to explore the cholinesterase inhibitory activity and anti-Aβ aggregation activity of the isolates in vitro and in silico. The bioactivity evaluation results highlighted the prospects of 1, 13, and 14 as novel categories of neurological agents.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145261344","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

Aminocatalytic 1,6-Addition of 2-Benzyl-3-furaldehyde to 3-Cyano-4-styrylcoumarins: A Dearomative Approach for the Synthesis of Furan–Coumarin Hybrids 氨基催化1,6加成2-苄基-3-呋喃醛至3-氰基-4-苯乙烯香豆素：呋喃-香豆素杂化物的脱芳香合成方法

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-10-11 DOI: 10.1021/acs.joc.5c01406

Aleksandra Topolska, Artur Przydacz, Lesław Sieroń, Anna Skrzyńska, Alberto Fraile, Jose Alemán, Łukasz Albrecht

引用次数: 0