The Journal of Organic Chemistry最新文献_第10页

Stereoselective Synthesis of Maralixibat via VO(acac)2/Schiff Base-Catalyzed Asymmetric Oxidation of Its Sulfide Intermediate 通过 VO(acac)2/希夫碱催化硫化物中间体的不对称氧化作用立体选择性合成马拉利西巴特

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01443

Ziyu Peng, Mercy Mpofo, Zheng Jie, Long Ye

引用次数: 0

One Pot Synthesis of C3-Sulfurized Imidazolo [1,2-a] Pyridines 一锅合成 C3 硫化咪唑并 [1,2-a] 吡啶

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01524

Ya-Dan Zhang, Zhi-Peng Guan, Zhi-Bing Dong

引用次数: 0

Polynitro-1,2,4-triazole Energetic Materials with N-Amino Functionalization 具有 N-氨基官能团的多硝基-1,2,4-三唑高能材料

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01771

Xinyang Lu, Xiangyang Lin, Haifeng Huang, Jun Yang

{"title":"Polynitro-1,2,4-triazole Energetic Materials with N-Amino Functionalization","authors":"Xinyang Lu, Xiangyang Lin, Haifeng Huang, Jun Yang","doi":"10.1021/acs.joc.4c01771","DOIUrl":"https://doi.org/10.1021/acs.joc.4c01771","url":null,"abstract":"Trinitromethyl and N-amino groups were innovatively incorporated into the framework of 1,2,4-triazole, resulting in 1-amino-5-nitro-3-(trinitromethyl)-1,2,4-triazole (2). Ammonium and hydrazinium salts of 1-amino-5-nitro-3-(dinitromethyl)-1,2,4-triazole were synthesized by acidification, extraction, and neutralization with bases from the potassium salt. All of the newly prepared energetic compounds were comprehensively characterized by using infrared spectroscopy, elemental analysis, nuclear magnetic resonance spectroscopy, and single crystal X-ray diffraction. Compound 2 exhibits favorable properties such as positive oxygen balance (OBCO2 = 5.8%), high density (1.88 g cm–1), good detonation performances (vD = 8937 m s–1, P = 35.5 GPa), and appropriate friction sensitivity (FS = 144 N). The potassium salt 3 demonstrates good thermal decomposition temperature (181 °C) and high density (1.98 g cm–1), while the ammonium salt and hydrazinium salt also display good thermal decomposition temperatures of 183 and 176 °C, respectively. Among these compounds, the ammonium salt exhibits the lowest mechanical sensitivities (FS = 144 N, IS = 6 J).","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142237209","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

Copper-Catalyzed α-Alkylation of Aryl Acetonitriles with Benzyl Alcohols 铜催化的芳基乙腈与苄醇的α-烷基化反应

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01662

Marianna Danopoulou, Leandros P. Zorba, Athanasia P. Karantoni, Demeter Tzeli, Georgios C. Vougioukalakis

引用次数: 0

A DFT Mechanistic Study on the Aza-Aldol Reaction of Boron Aza-Enolates: Relative Stability of Six-Membered Transition State and Its Relevance to the Coordination Mode of the Leaving Group 硼氮杂环戊醇的氮杂环-醛醇反应的 DFT 力学研究：六元过渡态的相对稳定性及其与离去基团配位模式的相关性

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c00957

Sho Miyakawa, Ray Miyazaki, Tomoya Miura, Jun-ya Hasegawa

{"title":"A DFT Mechanistic Study on the Aza-Aldol Reaction of Boron Aza-Enolates: Relative Stability of Six-Membered Transition State and Its Relevance to the Coordination Mode of the Leaving Group","authors":"Sho Miyakawa, Ray Miyazaki, Tomoya Miura, Jun-ya Hasegawa","doi":"10.1021/acs.joc.4c00957","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00957","url":null,"abstract":"The mechanism of the aza-aldol reaction between boron aza-enolate and benzaldehyde is investigated by using density functional theory calculations. The result shows that the syn-E isomer is preferentially formed, consistent with experimental observations. The six-membered ring transition state (TS) with the boat form leads to the E isomer, while the more unstable chair TS does to the Z isomer. The preference of the syn isomer is determined by the interactions between the substituents of aza-enolate and benzaldehyde. Structural distortion and intrinsic reaction coordinate analyses of simplified model systems provide insights into the origin of the relative stability of the rate-determining TS with boat and chair forms. The boat TS is an early TS; thus, minimal structural distortions of the reactant are required to reach this TS. The Lewis pair interactions between the boron and imine groups during B–N elimination also influenced the relative stability of the TSs. This interaction involves the nitrogen lone pair in the boat TS, while the π(N═C) orbital is involved in the chair TS. The Lewis pair with the lone pair stabilizes the TS more than that with the π orbital. The boron aza-enolate with 9-BBN generates an ate complex and forms C–C bonds sequentially, whereas that with Bpin does not generate an ate complex and exhibits the concerted formation of B–O and C–C bonds. Thus, the higher electrophilicity of boron such as 9-BBN enhances the reactivity by facilitating the formation of the ate complex. A reaction design is proposed to reverse the syn/anti selectivity. Proof-of-concept DFT calculations suggested that the modification of the imine group would change the relative stability of the boat/chair TSs and give the anti-product.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142237062","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

Acid-Promoted Amination of Cyclohexenone for the Divergent Synthesis of p-Aminophenols and Tertiary Amines 对氨基苯酚和叔胺的歧化合成中的环己酮酸促胺化反应

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c00292

Li Liu, Jun Li, Ya Chen, Shanping Chen, Fuhong Xiao, Guo-Jun Deng

引用次数: 0

Synthesis of 2,3-Benzobicyclo[3.3.1]non-2-enes via a Cascade of Domino Carbocation Migration/Interrupted Ritter Reaction and Dienone-Phenol Rearrangement 通过多米诺碳位迁移/间断里特反应和二烯酮-苯酚重排的级联反应合成 2,3-苯并双环[3.3.1]壬-2-烯

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01516

Zhiwei Sun, Chuanjun Song, Yonggang Meng, Yingchao Dou

引用次数: 0

2-(1,1-Dicyanomethylene)rhodanine-Functionalized Oligothiophenes: A Structure-Property Investigation of Z/E Photoisomerization Behavior. 2-(1,1-二氰基亚甲基)罗丹宁官能化低聚噻吩：Z/E 光异构化行为的结构-性质研究。

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c00823

Cory T Kornman,Parag Das,Lei Li,Asmerom O Weldeab,Ion Ghiviriga,Ronald K Castellano

{"title":"2-(1,1-Dicyanomethylene)rhodanine-Functionalized Oligothiophenes: A Structure-Property Investigation of Z/E Photoisomerization Behavior.","authors":"Cory T Kornman,Parag Das,Lei Li,Asmerom O Weldeab,Ion Ghiviriga,Ronald K Castellano","doi":"10.1021/acs.joc.4c00823","DOIUrl":"https://doi.org/10.1021/acs.joc.4c00823","url":null,"abstract":"A series of oligothiophenes singly and doubly functionalized with dicyanorhodanine (RCN) units have been investigated to understand their Z/E photoisomerization behavior upon structural modulation. Monotopic RCN target molecules (1-Z-9-Z) were designed to observe the consequences of π-conjugation, solubilizing group substitution, and formylation of the thiophene units. In all cases, the Z isomer is obtained from synthesis as the thermodynamically stable isomer, whereas the E isomer is achieved through selective irradiation (including red light, λirr = 628 nm) as a Z/E mixture in solution. For the quarterthiophene entries, photoisomerization is inhibited, with photoirradiation resulting only in degradation. The result comports with concentration-dependent studies, which show that increasing π-conjugation results in greater aggregation and muted Z/E photoisomerization. Ditopic RCN targets (10-ZZ-12-ZZ), mimicking acceptor-donor-acceptor (A-D-A) oligomers relevant to OPV materials, also show evidence of photoisomerization in solution, with formation of Z,Z/Z,E mixtures at the photostationary state (PSS). Complementary ground- and excited-state DFT calculations show excellent agreement with the experimental findings. This comprehensive structure-property analysis is expected to both guide and caution the functional materials community with respect to the usage of photoisomerizable RCN-oligothiophenes for optoelectronic applications.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.354,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142245363","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

Base-Promoted One-Pot Strategy for Expeditious Assembly of Highly Functionalized Benzocoumarin Derivatives 快速组装高官能化苯并香豆素衍生物的碱催化单锅策略

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-18 DOI: 10.1021/acs.joc.4c01879

Fataneh Rakaee, Morteza Shiri, Behnaz Farajpour, Serveh Majedi, Mahsa Seraj, Fatemeh Moradkhani, Salman Taheri, Mohammad Reza Sadeghi-Dolatabadi, Soma Majedi

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Cu/Pd-Catalyzed Tandem Carbonylative Synthesis of Ester-Containing 3,4-Dihydroquinolin-2(1H)-one Derivatives from Alkyne-Tethered α-Bromocarbonyls 铜/钯催化的α-溴羰基串联羰基合成含酯的 3,4-二氢喹啉-2(1H)-酮衍生物

IF 4.354 2区化学

The Journal of Organic Chemistry Pub Date : 2024-09-17 DOI: 10.1021/acs.joc.4c01032

Jiajun Zhao, Jianwei Wang, Shangyuan Wang, Jun Ying

引用次数: 0