发布求助
文献互助 智能选刊 最新文献

The Journal of Organic Chemistry最新文献

筛选
英文 中文
The Construction of Novel Spirocyclic Frameworks with Cyclobutane through Rh(III)-Catalyzed [3 + 2]-Annulation between Quinoxalines and Alkynylcyclobutanols. 通过 Rh(III)-Catalyzed [3 + 2]-Annulation between Quinoxalines and Alkynylcyclobutanols，用环丁烷构建新型螺环框架。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-03 DOI: 10.1021/acs.joc.4c00505
Yi-Chi Gang, Lin Dong
{"title":"The Construction of Novel Spirocyclic Frameworks with Cyclobutane through Rh(III)-Catalyzed [3 + 2]-Annulation between Quinoxalines and Alkynylcyclobutanols.","authors":"Yi-Chi Gang, Lin Dong","doi":"10.1021/acs.joc.4c00505","DOIUrl":"10.1021/acs.joc.4c00505","url":null,"abstract":"<p><p>An effective synthesis strategy for the preparation of 1'<i>H</i>-spiro[indene-1,2'-quinoxaline] has been developed. This involves a Rh(III)-catalyzed [3 + 2]-annulation of quinoxalines with alkynylcyclobutanols. The developed protocol offers a straightforward method for the preparation of versatile heterocyclic compounds with a four-membered ring and is compatible with a wide range of functional groups.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118370","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
Telluride-Based Pillar[5]arene: A Recyclable Catalyst for Alkylation Reactions in Aqueous Solution. 碲基支柱[5]炔：水溶液中烷基化反应的可循环催化剂。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-04 DOI: 10.1021/acs.joc.4c00997
Patrick C Nobre, Pâmella Cordeiro, Ingrid C Chipoline, Victor Menezes, Kaila V S Santos, Alix Y Bastidas Ángel, Eduardo E Alberto, Vanessa Nascimento
{"title":"Telluride-Based Pillar[5]arene: A Recyclable Catalyst for Alkylation Reactions in Aqueous Solution.","authors":"Patrick C Nobre, Pâmella Cordeiro, Ingrid C Chipoline, Victor Menezes, Kaila V S Santos, Alix Y Bastidas Ángel, Eduardo E Alberto, Vanessa Nascimento","doi":"10.1021/acs.joc.4c00997","DOIUrl":"10.1021/acs.joc.4c00997","url":null,"abstract":"<p><p>The syntheses of previously unknown sulfide- and telluride-pillar[<i>n</i>]arenes are reported here. These macrocycles, among others, were tested as catalysts for alkylation reactions in aqueous solutions. Telluride-pillar[5]arene (<b>P[5]-TePh</b>) showed the best performance, emulating the behavior of the methyltransferase enzyme cofactor <i>S</i>-adenosyl-l-methionine. Using 1.0 mol % of <b>P[5]-TePh</b>, benzyl bromides reacted with NaCN/NaN<sub>3</sub> in water, yielding organic nitriles/azides. The catalyst was recycled and efficiently reused for up to six cycles. <sup>1</sup>H NMR experiments indicate a possible interaction between the substrate and <b>P[5]-TePh</b>'s cavity.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131204","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
Microbial Biotransformation of 1-Methyl-L-tryptophan into Herbicidal Indole Alkaloids by Endophytic Fungus Nigrospora chinensis GGY-3. 内生真菌 Nigrospora chinensis GGY-3 将 1-甲基-L-色氨酸经微生物生物转化为具有除草作用的吲哚生物碱。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01514
Biao Wang, Bo He, Chen Zuo, Yu Li, Ping Chen, Hao Li, Yonghao Ye, Wei Yan
{"title":"Microbial Biotransformation of 1-Methyl-L-tryptophan into Herbicidal Indole Alkaloids by Endophytic Fungus <i>Nigrospora chinensis</i> GGY-3.","authors":"Biao Wang, Bo He, Chen Zuo, Yu Li, Ping Chen, Hao Li, Yonghao Ye, Wei Yan","doi":"10.1021/acs.joc.4c01514","DOIUrl":"10.1021/acs.joc.4c01514","url":null,"abstract":"<p><p>Indole alkaloids are privileged secondary metabolites, and their production may be achieved by the microbial biotransformation of tryptophan analogues. By feeding 1-methyl-L-tryptophan (1-MT) into the culture of endophytic <i>Nigrospora chinensis</i> GGY-3, six novel (<b>1</b>-<b>6</b>) and seven known indole alkaloids (<b>7</b>-<b>13</b>) were generated. Their structures were elucidated by means of NMR spectroscopy, experimental electronic circular dichroism (ECD) spectra, and X-ray crystallography analysis. A Friedel-Crafts reaction was proposed as the key reaction responsible for the formation of the new compounds. Racemates <b>4</b> and <b>6</b> were separated into isomers by chiral HPLC, with their absolute configurations determined by X-ray and ECD calculation. Compounds <b>3</b>, <b>4</b>, and <b>8</b> display good herbicidal activity against dicotyledon weed <i>Eclipta prostrata</i>, of which <b>4</b> and <b>8</b> exhibited 88.50% and 100% inhibition rates on the radicle at 200 μg/mL, respectively, a similar effect compared to the positive control penoxsulam.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138620","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
Theoretical Study on the Biosynthesis of the Mandapamates: Mechanistic Insights Using Density Functional Theory. Mandapamates 生物合成的理论研究：使用密度泛函理论的机理认识。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-09 DOI: 10.1021/acs.joc.4c00859
Di Wang, Gerald Pattenden, Kam Loon Fow, Michael J Stocks, Jonathan D Hirst, Bencan Tang
{"title":"Theoretical Study on the Biosynthesis of the Mandapamates: Mechanistic Insights Using Density Functional Theory.","authors":"Di Wang, Gerald Pattenden, Kam Loon Fow, Michael J Stocks, Jonathan D Hirst, Bencan Tang","doi":"10.1021/acs.joc.4c00859","DOIUrl":"10.1021/acs.joc.4c00859","url":null,"abstract":"<p><p>Density functional theory (B3LYP-D3(BJ) and ωB97XD) calculations have been used to assess the stereochemical outcomes of the proposed transannular [4 + 2] cycloaddition pathway for the biosynthesis of mandapamate and isomandapamate from macrocyclic intermediates. Calculations reveal that the topological shift between macrocyclic conformers is vital in controlling the stereoselectivity of the downstream steps toward the isomeric mandapamates. A stepwise 4 + 2 type process is energetically favored over a concerted [4 + 2] pathway at room temperature, and is consistent with the stereochemistries found in the natural products.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152470","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
Synthesis of Sulfoxides by Palladium-Catalyzed Arylation of Sulfenate Anions with Aryl Thianthrenium Salts. 通过钯催化硫酸根阴离子与芳基噻蒽盐的芳基化反应合成氧化硫。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-03 DOI: 10.1021/acs.joc.4c01418
Feifei Jin, Qianqian Hu, Qiang Wang, Jing Sun, Kun Huang, Chao-Guo Yan, Ying Han, Haiyang Fei, Lei Wang
{"title":"Synthesis of Sulfoxides by Palladium-Catalyzed Arylation of Sulfenate Anions with Aryl Thianthrenium Salts.","authors":"Feifei Jin, Qianqian Hu, Qiang Wang, Jing Sun, Kun Huang, Chao-Guo Yan, Ying Han, Haiyang Fei, Lei Wang","doi":"10.1021/acs.joc.4c01418","DOIUrl":"10.1021/acs.joc.4c01418","url":null,"abstract":"<p><p>A novel and highly efficient Pd-catalyzed arylation of sulfenate anions with aryl thianthrenium salts is demonstrated. This procedure provides a practical protocol to synthesize various diaryl and alkyl aryl sulfoxides in moderate-to-good yields. The new approach shows mild reaction conditions, broad substrate scope, and good functional group tolerance.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118369","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
Asymmetric Remote Aldol Cyclization Reaction to Synthesize Trifluoromethylated Heterospirocyclic Frameworks. 不对称远程醛醇环化反应合成三氟甲基异螺环框架。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-05 DOI: 10.1021/acs.joc.4c01839
José Trujillo-Sierra, José Miguel Sansano, Jorge Pardos, Tomás Tejero, Pedro Merino, María de Gracia Retamosa
{"title":"Asymmetric Remote Aldol Cyclization Reaction to Synthesize Trifluoromethylated Heterospirocyclic Frameworks.","authors":"José Trujillo-Sierra, José Miguel Sansano, Jorge Pardos, Tomás Tejero, Pedro Merino, María de Gracia Retamosa","doi":"10.1021/acs.joc.4c01839","DOIUrl":"10.1021/acs.joc.4c01839","url":null,"abstract":"<p><p>The highly enantioselective organocatalytic synthesis of dihydropyran spirocyclic compounds bearing di- and trifluoromethyl groups by aldol cyclization reaction via trienamine using cyclic 2,5-dienones and different di- and trifluoromethylketones is described. Using a bifunctional aminothiourea catalyst, trifluoromethyl-functionalized dihydropyran spirocyclic products were obtained with good yields and enantioselectivities. Subsequent transformation with H<sub>2</sub> and Pd/C has allowed the synthesis of the tetrahydropyran structure with three stereocenters. The plausible reaction mechanism was investigated by computational methods.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131198","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
Carbon-Fluorine Activation in the Gas Phase: The Reactions of Benzyl C-F Bonds and Silyl Cations. 气相中的碳氟活化：苄基 C-F 键与硅基阳离子的反应。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01775
Damon J Hinz, Allison E Krajewski, Jeehiun K Lee
{"title":"Carbon-Fluorine Activation in the Gas Phase: The Reactions of Benzyl C-F Bonds and Silyl Cations.","authors":"Damon J Hinz, Allison E Krajewski, Jeehiun K Lee","doi":"10.1021/acs.joc.4c01775","DOIUrl":"10.1021/acs.joc.4c01775","url":null,"abstract":"<p><p>The activation of C-F bonds figures largely in both fundamental and applied chemical processes. Herein the activation of benzyl C-F bonds by silyl cations is examined both computationally and experimentally in the gas phase. The experimental rate constant values obtained herein have not heretofore been measured and provide insight into the intrinsic ability of silyl cations to activate C-F bonds. Trends in reactivity and correlations between theoretical and experimental data are discussed in the context of C-F bond cleavage.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138617","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
Triflic Anhydride-Mediated Approach to Furo[3,2-b]furans from Diacetonide Protected Furanoses. 三酸酐介导的从二丙酮保护呋喃糖制备呋喃并[3,2-b]呋喃的方法。
IF 3.3 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-09-06 DOI: 10.1021/acs.joc.4c01067
Tariq Ahmad Dar, Mohammad Yaqoob Bhat, Norein Sakander, Qazi Naveed Ahmed
{"title":"Triflic Anhydride-Mediated Approach to Furo[3,2-<i>b</i>]furans from Diacetonide Protected Furanoses.","authors":"Tariq Ahmad Dar, Mohammad Yaqoob Bhat, Norein Sakander, Qazi Naveed Ahmed","doi":"10.1021/acs.joc.4c01067","DOIUrl":"10.1021/acs.joc.4c01067","url":null,"abstract":"<p><p>Trifluoromethanesulfonic anhydride (Tf<sub>2</sub>O) exhibits excellent reactivity as an electrophile, serving as a highly versatile reagent in diverse chemical transformations. Herein, we report an operationally simple, efficient, unique, and practical one-step strategy for synthesizing diverse valuable structures bearing furo[3,2-<i>b</i>]furans core leveraging Tf<sub>2</sub>O's promoted reactivity of nitriles with diacetonide protected furanose. Furthermore, we demonstrate the potential of furo[3,2-<i>b</i>]furan as a precursor for complex structures through 1,3-dipolar cycloaddition.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138625","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
Leap from Diradicals to Tetraradicals by Topological Control of π-Conjugation 通过拓扑控制π共轭实现从二元杂环到四元杂环的飞跃
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1021/acs.joc.4c01375
Sergi Betkhoshvili, Jordi Poater, Ibério de P. R. Moreira, Josep Maria Bofill
{"title":"Leap from Diradicals to Tetraradicals by Topological Control of π-Conjugation","authors":"Sergi Betkhoshvili, Jordi Poater, Ibério de P. R. Moreira, Josep Maria Bofill","doi":"10.1021/acs.joc.4c01375","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01375","url":null,"abstract":"In this work, we explore the series of diradical(oid)s based on 2,2′-(5,11-dihydroindolo[3,2-<i>b</i>]carbazole-3,9-diyl)dimalononitrile (further referred to as <b>PH</b>). Hydrogen atoms in the central benzenoid (CB) ring of <b>PH</b> are substituted by the series of substituents with various lengths of π-conjugated chain and electron-donating or electron-withdrawing properties to study how they modulate the diradical character of the parent compound. The diradical character of molecules increases up to 88–89% by two groups doubly bonded to both sides of the CB ring of <b>PH</b> in <i>para</i> relative positions. This breaks the direct π-conjugation between unpaired electrons that gives rise to two radical centers and restricts the minimal polyradical identity of the compound to diradical. We show that diradicals and tetraradicals can be designed, and their polyradical character can be modulated by controlling the topology of π-conjugation as long as there is sufficient aromatic stabilization. Henceforth, the bridge between diradicals and tetraradicals is established, leading to the tetraradical(oid) molecule, which has been predicted to have narrow low-spin to high-spin energy gaps in our recent Letter.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142247225","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
Probing the Influence of Alkyne Substitution on the Electronic and Magnetic Properties of Diindeno[1,2-b;1',2'-i]anthracenes. 探究炔取代对二茚并[1,2-b;1',2'-i]蒽电子和磁性能的影响。
IF 4.354 2区 化学
The Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1021/acs.joc.4c01500
Efrain Vidal,Lev N Zakharov,Carlos J Gómez-García,Michael M Haley
{"title":"Probing the Influence of Alkyne Substitution on the Electronic and Magnetic Properties of Diindeno[1,2-b;1',2'-i]anthracenes.","authors":"Efrain Vidal,Lev N Zakharov,Carlos J Gómez-García,Michael M Haley","doi":"10.1021/acs.joc.4c01500","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01500","url":null,"abstract":"To further the ability to manipulate the properties of open-shell molecules, logical and incremental modifications to molecular structure are key steps that provide fine-tuning of established diradicaloid scaffolds. We report the synthesis of an electronically \"pure\" diradicaloid based on a 2,6-anthroquinoidal core where the once necessary ethynyl \"wings\" are removed. Through the simplification of the overall electronic structure, the singlet-triplet energy gap increases by 0.3-0.4 kcal mol-1 in the reported diradicaloids while avoiding significant disruption to their optoelectronic properties.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142273422","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
首页 上一页 下一页 尾页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术官方微信