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(S,Z)-1,4-Bis(benzyloxy)hexa-3,5-dien-2-ol (S,Z)-1,4-双(苄氧基)己-3,5-二烯-2-醇
Molbank Pub Date : 2024-07-10 DOI: 10.3390/m1848
Akihiro Iyoshi, Yoshinori Miyazaki, Masakazu Tanaka, Atsushi Ueda
{"title":"(S,Z)-1,4-Bis(benzyloxy)hexa-3,5-dien-2-ol","authors":"Akihiro Iyoshi, Yoshinori Miyazaki, Masakazu Tanaka, Atsushi Ueda","doi":"10.3390/m1848","DOIUrl":"https://doi.org/10.3390/m1848","url":null,"abstract":"Naturally occurring carbohydrates serve as useful building blocks, and various derivatives have been employed in natural product syntheses. For instance, some aldoses can be converted to 1,3-dienes via the Wittig reaction at the anomeric carbon, accompanied by the E2 elimination of the C3-alkoxy group. However, there are few examples of terminal 1,3-diene synthesis. We report the synthesis of (S,Z)-1,4-bis(benzyloxy)hexa-3,5-dien-2-ol, featuring a terminal 1,3-diene and chiral secondary alcohol, derived from 2,3,5-tri-O-benzyl-d-arabinofuranose with methyltriphenylphosphonium bromide and potassium tert-butoxide in a single step. The synthesized terminal 1,3-diene demonstrated effective reactivity in a cross-metathesis reaction with cis-1,4-diacetoxy-2-butene.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"48 17","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141659968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Methyl and Benzyl (Ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-d-glucopyranosyl)uronate 3,4-二-O-苄基-2-O-苯甲酰基-1-硫代-β-d-吡喃葡萄糖基）脲酸甲酯和苄酯
Molbank Pub Date : 2024-07-09 DOI: 10.3390/m1847
Hannah S. Wootton, Gavin J. Miller
{"title":"Methyl and Benzyl (Ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-d-glucopyranosyl)uronate","authors":"Hannah S. Wootton, Gavin J. Miller","doi":"10.3390/m1847","DOIUrl":"https://doi.org/10.3390/m1847","url":null,"abstract":"Methyl and benzyl (ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-glucopyranosyl)uronate were synthesised from a protected thioglycoside in three steps. A regioselective ring opening of the benzylidene acetal with BH3.THF generated C6-OH material, which was subsequently oxidised using biphasic TEMPO/BAIB conditions. The resultant uronic acid was esterified with either a methyl or benzyl moiety. The products were obtained on a multigram scale and fully characterised by 1H, 13C and 2D NMR, alongside MS and IR analysis.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"101 49","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141666465","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A (2-(Pyrrolidin-1-yl)ethan-1-olate)(1-oxo-3-phenyl-1,4-dihydronaphthalen-2-olate) μ-Oxo-Bridged Dicopper(II) Dimeric Complex 一种(2-(吡咯烷-1-基)乙烷-1-醇)(1-氧代-3-苯基-1,4-二氢萘-2-醇)μ-氧桥双铜(II)二聚体络合物
Molbank Pub Date : 2024-07-05 DOI: 10.3390/m1846
Rylan Artis, Clifford W. Padgett, Kennedy Musso, Nathaniel Shank, Allison Marks, Brandon P. Quillian
{"title":"A (2-(Pyrrolidin-1-yl)ethan-1-olate)(1-oxo-3-phenyl-1,4-dihydronaphthalen-2-olate) μ-Oxo-Bridged Dicopper(II) Dimeric Complex","authors":"Rylan Artis, Clifford W. Padgett, Kennedy Musso, Nathaniel Shank, Allison Marks, Brandon P. Quillian","doi":"10.3390/m1846","DOIUrl":"https://doi.org/10.3390/m1846","url":null,"abstract":"The reaction of 2-(1H-pyrrol-1-yl)ethanol with 3-hydroxyflavone in the presence of copper(II) bromide yielded a dimeric copper(II) complex, [μ-O-(κ2-O,O-flav)(κ2-N,O-2PEO)Cu]2 (1) (flav = 3-hydroxyflavonolate; 2PEO = 2-(1H-pyrrol-1-yl)ethanolate) with both the flav and 2PEO ligands bound to the copper(II) atom in a κ2-bonding mode. The dimer is held electrostatically by bridging oxygen atoms between two copper atoms. Complex 1 was characterized by single-crystal X-ray diffraction, infrared, and UV-Vis spectroscopy, elemental analysis, and melting point determination. The complex crystallizes in the monoclinic space group P21/n (14) with cell values of a = 11.85340(10) Å, b = 8.51480(10) Å, c = 23.8453(2) Å; β = 99.3920(10)°.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":" 8","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141675061","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
trans-catena-Poly[[(bis-(µ-N,N′-bis[(pyridin-3-yl)methyl]ethanediamide))-diaqua-cadmium(II)] bis(nitrate) tetrahydrate)] 反式-卡泰纳-多[[(双(µ-N,N′-双[(吡啶-3-基)甲基]乙二酰胺))-二夸父镉(II)]双（硝酸）四水合物]]
Molbank Pub Date : 2024-07-03 DOI: 10.3390/m1845
Anna Caria, E. Podda, M. Aragoni, Riccardo Lai, Anna Pintus, M. Arca
{"title":"trans-catena-Poly[[(bis-(µ-N,N′-bis[(pyridin-3-yl)methyl]ethanediamide))-diaqua-cadmium(II)] bis(nitrate) tetrahydrate)]","authors":"Anna Caria, E. Podda, M. Aragoni, Riccardo Lai, Anna Pintus, M. Arca","doi":"10.3390/m1845","DOIUrl":"https://doi.org/10.3390/m1845","url":null,"abstract":"The reaction between cadmium nitrate tetrahydrate and N,N′-bis(pyridin-3-ylmethyl)oxalamide (L) in a 1:3 molar ratio in a water/acetonitrile (1:6 v/v) mixture afforded single crystals of compound 1 suitable for X-ray diffraction analysis. Compound 1 consists of the coordination polymer (CP) [[Cd(L)2(OH2)2](NO3)2·4H2O]∞, in which CdII ions are bridged by neutral L antiperiplanar N-ligands in a wavy ribbon fashion developed along the c-axis. Two trans-disposed water molecules complete the pseudo-octahedral coordination geometry of the metal ion. The crystal packing of 1 revealed the interplay between π–π stacking interactions and an intricate hydrogen-bonded network involving oxalamides, nitrates, and water molecules. The donor properties of L and the intermolecular interactions in compound 1 are interpreted based on hybrid-DFT calculations.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"104 s410","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141682809","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Introducing Bis(5-(Trifluoromethyl)pyridin-2-yl)amine Chelating Unit via Pd-Catalyzed Amination 通过钯催化胺化引入双(5-(三氟甲基)吡啶-2-基)胺螯合单元
Molbank Pub Date : 2024-06-04 DOI: 10.3390/m1831
Nikolay A. Korinskiy, A. Abel, Violetta A. Ionova, S. Bezzubov, A. Averin, Irina P. Beletskaya
{"title":"Introducing Bis(5-(Trifluoromethyl)pyridin-2-yl)amine Chelating Unit via Pd-Catalyzed Amination","authors":"Nikolay A. Korinskiy, A. Abel, Violetta A. Ionova, S. Bezzubov, A. Averin, Irina P. Beletskaya","doi":"10.3390/m1831","DOIUrl":"https://doi.org/10.3390/m1831","url":null,"abstract":"We report a one-step synthesis of trifluoromethyl-substituted di(pyridin-2-yl)amine-based ligands. N-(hetero)aryl-substituted bis(5-(trifluoromethyl)pyridin-2-yl)amines were obtained from 2-bromo-5-(trifluoromethyl)pyridine and corresponding aromatic amines via Pd-catalyzed amination reaction in the presence of a Pd(dba)2/BINAP catalytic system. Four new ligands were prepared in good to high yields and characterized by NMR, IR spectroscopies and mass spectrometry. The structure of one of the products was additionally supported by X-ray analysis.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"17 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141266405","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
(±)-R,S-2-Chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide (±)-R,S-2-Chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide
Molbank Pub Date : 2024-06-03 DOI: 10.3390/m1830
D. Dimitrova, S. Manolov, D. Bojilov, I. Ivanov, P. Nedialkov
{"title":"(±)-R,S-2-Chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide","authors":"D. Dimitrova, S. Manolov, D. Bojilov, I. Ivanov, P. Nedialkov","doi":"10.3390/m1830","DOIUrl":"https://doi.org/10.3390/m1830","url":null,"abstract":"In this study, we report the synthesis of (±)-2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide through the reaction of 7-amino-4-methyl-2H-chromen-2-one with (±)-2-chloro-2-phenylacetyl chloride. The in vitro anti-inflammatory activity of the new compound was evaluated, and the results indicated that it exhibited superior activity compared to the standard, ibuprofen. The bio-functional hybrid compound underwent thorough detailed characterization utilizing 1H and 13C NMR, UV, and mass spectral analysis.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"33 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141273019","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
2S-(1RS-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine 2S-(1RS-苄氧基-己-5-烯基)-2,3-二氢-1,4-苯并二恶烷
Molbank Pub Date : 2024-04-24 DOI: 10.3390/m1812
Angelica Artasensi, L. Fumagalli
{"title":"2S-(1RS-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine","authors":"Angelica Artasensi, L. Fumagalli","doi":"10.3390/m1812","DOIUrl":"https://doi.org/10.3390/m1812","url":null,"abstract":"In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling 1H and 2D Nuclear Overhauser Effect NMR techniques, the configuration of the two diastereomers 2S-(1R-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine and 2S-(1S-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine, which are useful to synthetize analogs of the potent and highly selective dipeptidyl peptidase IV and carbonic anhydrase inhibitor recently published.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"26 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140661849","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
5,5′-Thiobis(3-bromoisothiazole-4-carbonitrile) 5,5′-硫代双(3-溴异噻唑-4-甲腈)
Molbank Pub Date : 2024-04-24 DOI: 10.3390/m1813
Andreas S. Kalogirou, P. A. Koutentis
{"title":"5,5′-Thiobis(3-bromoisothiazole-4-carbonitrile)","authors":"Andreas S. Kalogirou, P. A. Koutentis","doi":"10.3390/m1813","DOIUrl":"https://doi.org/10.3390/m1813","url":null,"abstract":"The reaction of sodium 2,2-dicyanoethene-1,1-bis(thiolate) with bromine (2 equiv.) in CCl4 gave 3,5-dibromoisothiazole-3-carbonitrile and 5,5′-thiobis(3-bromoisothiazole-4-carbonitrile) in 7% and 18% yields, respectively. The latter novel compound was fully characterized.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"51 25","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140662156","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chloro(η2,η2-cycloocta-1,5-diene){1-benzyl-3-[(S)-2-hydroxy-1-methylethyl]benzimidazol-2-ylidene}rhodium(I) 氯(η2,η2-环辛烷-1,5-二烯){1-苄基-3-[(S)-2-羟基-1-甲基乙基]苯并咪唑-2-亚基}铑(I)
Molbank Pub Date : 2024-04-19 DOI: 10.3390/m1811
S. Sakaguchi, Shogo Matsuo
{"title":"Chloro(η2,η2-cycloocta-1,5-diene){1-benzyl-3-[(S)-2-hydroxy-1-methylethyl]benzimidazol-2-ylidene}rhodium(I)","authors":"S. Sakaguchi, Shogo Matsuo","doi":"10.3390/m1811","DOIUrl":"https://doi.org/10.3390/m1811","url":null,"abstract":"Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl2(p-cymene)]2 and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag2O method. In this study, we successfully synthesized [RhX(cod)(NHC)] complexes through a one-pot deprotonation route. The hydroxyalkyl-substituted benzimidazolium salt reacted with [Rh(OH)(cod)]2 in THF at room temperature, affording the corresponding monodentate NHC/Rh(I) complex in nearly quantitative yield. The rhodium complex was characterized using NMR, HRMS measurement, and elemental analysis.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":" 84","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140683718","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chloro(η2,η2-Cycloocta-1,5-Diene){1-[(2-[(S)-1-(Hydroxymethyl)-3-Methylbutyl]Amino)-2-Oxoethyl]-3-(1-Naphthalenylmethyl)Benzimidazol-2-Ylidene}Rhodium(I) 氯(η2,η2-环辛烷-1,5-二烯){1-[(2-[(S)-1-(羟甲基)-3-甲基丁基]氨基)-2-氧代乙基]-3-(1-萘甲基)苯并咪唑-2-亚基}铑(I)
Molbank Pub Date : 2024-04-19 DOI: 10.3390/m1810
S. Sakaguchi, Shogo Matsuo
{"title":"Chloro(η2,η2-Cycloocta-1,5-Diene){1-[(2-[(S)-1-(Hydroxymethyl)-3-Methylbutyl]Amino)-2-Oxoethyl]-3-(1-Naphthalenylmethyl)Benzimidazol-2-Ylidene}Rhodium(I)","authors":"S. Sakaguchi, Shogo Matsuo","doi":"10.3390/m1810","DOIUrl":"https://doi.org/10.3390/m1810","url":null,"abstract":"Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]2 (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H bond of the azolium ring in the hydroxyamide-substituted benzimidazolium salt 1. This reaction between 1 and 2 proceeded in THF at room temperature without temperature control, affording the desired NHC/Rh complex 3 in excellent yield. The characterization of complex 3 was accomplished through NMR and HRMS analyses, revealing its existence as a diastereomeric mixture of two NHC/Rh complexes. Furthermore, its catalytic performance was briefly evaluated in the reaction between 2-naphthaldehyde (5) and phenylboronic acid (6).","PeriodicalId":509184,"journal":{"name":"Molbank","volume":" 77","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140683649","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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