Journal of Organic Chemistry最新文献

Ligand Control of Geometric Selectivity in Protosilylation of Acyclic α-Substituted α,β-Unsaturated N-Sulfinyl Ketimines. 无环α-取代α，β-不饱和n -亚砜基酮胺原硅基化几何选择性的配体控制

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-05 DOI: 10.1021/acs.joc.5c01266

Jing-Wen Ma,Xiao-Ling Liu,Chong-Dao Lu

引用次数: 0

Bench-Stable Imine Surrogates for the Synthesis of α-Carbonylenamines. 合成α-羰基胺的稳定亚胺替代物。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-05 DOI: 10.1021/acs.joc.5c00574

Shun He,Jizhou Feng,Huan Yang,Jun Huang,Jilan Long,Huacheng Xu,Yun He

引用次数: 0

Practical Machine Learning Strategies 4: Using Neural Networks to Replicate Proton and 13C NMR Chemical Shifts Obtained from ωB97X-D/6-31G* Density Functional Calculations. 实用机器学习策略4：使用神经网络复制从ωB97X-D/6-31G*密度函数计算中获得的质子和13C NMR化学位移。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-05 DOI: 10.1021/acs.joc.5c00927

Thomas Hehre,Philip E Klunzinger,Bernard J Deppmeier,William Sean Ohlinger,Warren J Hehre

{"title":"Practical Machine Learning Strategies 4: Using Neural Networks to Replicate Proton and 13C NMR Chemical Shifts Obtained from ωB97X-D/6-31G* Density Functional Calculations.","authors":"Thomas Hehre,Philip E Klunzinger,Bernard J Deppmeier,William Sean Ohlinger,Warren J Hehre","doi":"10.1021/acs.joc.5c00927","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00927","url":null,"abstract":"Described are neural networks that accurately reproduce proton and 13C chemical shifts obtained from ωB97X-D/6-31G*//ωB97X-D/6-31G* density functional model GIAO calculations. They support uncharged, closed-shell molecules comprising H, C, N, O, F, S, Cl, and Br. Development involved training to ≈2.7 million equilibrium geometry and chemical shift calculations for a diverse collection of organic molecules (including synthetic drugs and natural products). Referenced to ωB97X-D/6-31G*//ωB97X-D/6-31G* calculations, chemical shifts from neural networks for 601 marine natural products show RMS errors of 0.05 ppm (proton) and 0.76 ppm (13C). RMS errors of 0.09 ppm (proton) and 1.02 ppm (13C) shifts result when equilibrium geometries from a previously described \"estimated ωB97X-D/6-31G*\" neural network model (trained to reproduce ωB97X-D/6-31G* geometries) are utilized. A second assessment of experimental 13C chemical shifts for 246 natural products is provided. Using neural network models to provide both geometries and chemical shifts: 45% of 13C shifts reproduce experimental values within 1 ppm, 73% within 2 ppm, and 86% within 3 ppm. Utilizing neural network models for both equilibrium geometries and chemical shifts reduces the computational time required for accurate proton and 13C chemical shifts from tens to hundreds of minutes to just a few seconds per molecule.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144777856","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

Palladium-Catalyzed Denitrogenative Carbonylation of Benzotriazinones in Batch and Flow: Divergent Synthesis of Phthalimides and Phthalic Diamides. 钯催化苯并三嗪酮的间歇和流动脱氮羰基化：邻苯二胺和邻苯二胺的发散合成。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-05 DOI: 10.1021/acs.joc.5c00891

Jorge García-Lacuna,Ángel Manu Martínez,Gema Domínguez,Javier Pérez-Castells

引用次数: 0

Accessing 3-Sulfonated Vinylsilanes via Sulfonylation of α-Bromoallylsilane Involving Photoinduced Radical Sulfur Dioxide Insertion. 光诱导二氧化硫自由基插入α-溴丙基硅烷磺化制备3-磺化乙烯基硅烷。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-04 DOI: 10.1021/acs.joc.5c01237

Jie Wang,Yang Luo,Shuo Gao,Xiaoqing Li,Xiangsheng Xu

引用次数: 0

Selective Functionalization of 2-Amino-Azoles with Methanol and Ethanol Using a Pincer-(NHC)Mn(I) Complex. 钳子-(NHC)Mn(I)配合物与甲醇和乙醇选择性功能化2-氨基偶氮。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-04 DOI: 10.1021/acs.joc.5c01191

Adarsha Mandal,Manoj Pradhan,Soumen Giri,Srabani Nandi,Sabuj Kundu

引用次数: 0

Brønsted Acid-Promoted Oxa-Pictet-Spengler Reaction for the Synthesis of Indole-Fused Pyran Derivatives. Brønsted酸促进Oxa-Pictet-Spengler反应合成吲哚-吡喃衍生物。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-04 DOI: 10.1021/acs.joc.5c01063

Zhuohao Chen,Yasheng Cao,Rong Huang,Xiangyuan Yao,Fuhong Xiao,Guo-Jun Deng

引用次数: 0

Optimizing the Catalytic Performance of Amine-Functionalized 4CzIPN Derivatives by Investigation of the Twisted Intramolecular Charge Transfer Effect. 通过研究分子内扭曲电荷转移效应来优化胺功能化4CzIPN衍生物的催化性能。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-04 DOI: 10.1021/acs.joc.5c00698

Angela Münch,Jonas Klopf,Laura Sojka,Laurin Brandhoff,Holger Helten,Bernd Engels,Juergen Seibel

{"title":"Optimizing the Catalytic Performance of Amine-Functionalized 4CzIPN Derivatives by Investigation of the Twisted Intramolecular Charge Transfer Effect.","authors":"Angela Münch,Jonas Klopf,Laura Sojka,Laurin Brandhoff,Holger Helten,Bernd Engels,Juergen Seibel","doi":"10.1021/acs.joc.5c00698","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00698","url":null,"abstract":"Amine-functionalized 4CzIPN derivatives exhibit extraordinary redox potentials in their excited state but are still often found to be ineffective in catalytic transformations. A possible reason for this disadvantage is the twisted intramolecular charge transfer (TICT) effect, which is known to affect the photophysical properties and thus the catalytic efficiency of such dyes. We have designed four amine-bearing triazole-linked 4CzIPN derivatives based on structural motifs that are known to enhance or suppress the transition into the TICT state through stereoelectronic properties in order to better understand and overcome the limitations possibly caused by this phenomenon. By applying these derivatives in challenging oxidative and reductive transformations, such as the bromination of anisole or the reductive dechlorination of methyl 4-chlorobenzoate, we demonstrated that some of the new compounds are more powerful catalysts than 4CzIPN. This seems to indicate that considerations about the TICT effect are a powerful tool for harnessing the outstanding redox powers of amine-functionalized organic photocatalysts in organic synthesis. However, quantum chemical investigations yield detailed insights into the photoelectronic features of the dyes, which modify the assumptions to some extent.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144769776","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

O-H Bond Energies of 1-Hydroxy-2,2,6,6-tetramethylpiperidine and Its Derivatives. 1-羟基-2,2,6,6-四甲基哌啶及其衍生物的O-H键能。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-04 DOI: 10.1021/acs.joc.5c00518

Xiao Zhao,Bing Zhong,Jin-Dong Yang,Jin-Pei Cheng

引用次数: 0

Axially Chiral 4,4'-Bithiopyran Atropisomer Dimerized by Thiopyran-Fused [4]Helicene: Synthesis, Chiral Properties, and Supramolecular Behaviors. 轴手性4,4'-双硫代吡喃-螺旋烯二聚体：合成、手性和超分子行为。

IF 4.354 2区化学

Journal of Organic Chemistry Pub Date : 2025-08-04 DOI: 10.1021/acs.joc.5c01048

Min Wang,Gang Zhou

{"title":"Axially Chiral 4,4'-Bithiopyran Atropisomer Dimerized by Thiopyran-Fused [4]Helicene: Synthesis, Chiral Properties, and Supramolecular Behaviors.","authors":"Min Wang,Gang Zhou","doi":"10.1021/acs.joc.5c01048","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01048","url":null,"abstract":"Despite the progress in atropisomers and helicenes with axial and helical chirality, the construction of axially chiral compounds by directly dimerizing two helicenes remains challenging. Herein, a thiopyran-fused [4]helicene NCT is dimerized to 4,4'-bithiopyran atropisomer BNCT with axial and helical chirality. The variable-temperature 1H NMR and UV-vis spectroscopies indicate that atropisomer BNCT rotates around the axis upon temperature changes. The enantiomeric interconversion pathway of atropisomer BNCT is systematically investigated by density functional theory calculation. Although the dihedral angle between the two thiopyran rings is 63.0° revealed by single-crystal analysis, the dichloromethane solution of BNCT displays a significant bathochromic shift of 56 nm for the absorption maximum in comparison to that for NCT, suggesting the effective conjugation extension along the atropisomer axis. The R- and S-enantiomers of BNCT have been successfully separated, and their electronic circular dichroism spectra exhibit a mirror-image relationship. Most interestingly, octafluoronaphthalene (OFN) can be inserted between the BNCT molecules to form supramolecular interactions with a host-guest ratio of 1:1. The single cocrystal of BNCT and OFN suggested that the supramolecular behaviors originate from the donor-acceptor interactions between BNCT and OFN molecules, although BNCT presents a twisted molecular skeleton.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"58 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-08-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144777864","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