10368-44-2Relevant articles and documents
Convenient and inexpensive synthesis of (1R,2R)-trans-1-amino-6-nitroindan- 2-ol
Kozhushkov, Sergei I.,Yufit, Dmitrii S.,De Meijere, Armin
, p. 255 - 265 (2005)
Racemic trans-1-amino-6-nitroindam-2-ol (rac-1) has been prepared in five steps from inexpensive indene (7) in 96% overall yield. The key step was a direct nitration of the known trans-1-aminoindan-2-ol (rac-9) which gave sulfuric acid mono-(rac-trans-1-amino-6-nitroindan-2-yl) ester (rac-10) in quantitative yield. The latter was quantitatively converted into rac-1 by treatment with aqueous 6 N HCl and then ammonia solutions. The same transformations of (1R,2R)-9 [prepared by deracemization of rac-9 with (-)-dibenzoyl-L-tartaric acid (DBT)] proceeded without loss of the optical activity. Deracemization of rac-1 applying (+)-(5)-L-mandelic acid (MA) furnished (1R,2R)-1 and (1s,2s)-1 in 34 and 17% yield, respectively, with e.e. ≥ 98 and 97.6%, respectively. Procedures for recycling of the chiral auxiliaries DBT and MA are also described. The structures of key intermediates were confirmed by X-ray crystal structure analysis.
Hydrogen bonding of hydroxy groups to carbanions in indenide and fluorenide derivatized alcohols directly observed by UV, IR, and NMR spectroscopy
Mc Ewen, Ian,R?nnqvist, Mats,Ahlberg, Per
, p. 3989 - 3996 (1993)
For investigation of hydrogen bonding to carbanions a number of carbanions containing hydroxy groups have been designed and synthesized. The carbanions were of the type R′-CR2-CHR-CR2-OH, with R′ being an indenide or a fluorenide group and R a methyl group or a hydrogen, and were generated from the corresponding indenes and fluorenes. Intramolecular hydrogen bonding was observed by UV, IR, and NMR spectroscopy in both polar [dimethyl sulfoxide (DMSO) and tetrahydrofuran (THF)] and apolar (benzene and toluene) non-hydrogen bond donor solvents with properly designed carbanions. In the latter solvents cryptand 211 was used for complexation of the counter Li+ cation. For some derivatives the presence of both intramolecular hydrogen bonding to the carbanion and intermolecular hydrogen bonding of the hydroxy group to the solvent was observed. The UV spectroscopy indicated the perturbation of the proton accepting carbanion and IR and NMR spectroscopy showed the effect of the hydrogen bonding on the proton donating OH group.
Synthesis of poly(indene carbonate) from indene oxide and carbon dioxide - A polycarbonate with a rigid backbone
Darensbourg, Donald J.,Wilson, Stephanie J.
, p. 18610 - 18613 (2011)
The catalytic coupling of carbon dioxide with indene oxide utilizing (salen)Co(III)-2,4-dinitrophenoxide in the presence of an onium salt is presented. X-ray structural data for indene oxide monomer as well as cisindene carbonate display near planarity of the fused cyclopentene and benzene rings. Low temperature (0 °C) is required to selectively afford copolymer vs cyclic carbonate from the coupling reactions of CO2 and indene oxide. The produced poly(indene carbonate) samples have molecular weights of up to 7100 Da, with corresponding glass transition temperatures of up to 134 °C, the highest yet reported for polycarbonates produced from CO2/epoxides coupling. Poly(indene carbonate) is thermally stable up to 249 °C. The polymerizations are well controlled, with PDI values ≤1.3.
Synthesis of new indanyl nucleoside analogues and their biological evaluation on hepatitis C virus (HCV) replicon
Gómez, Matías E.,Gentile, Emiliano A.,Florencia Martini,Cuestas, María L.,Mathet, Verónica L.,Moltrasio, Graciela Y.,Moglioni, Albertina G.
, (2019)
Here, we report a convenient synthetic procedure for the preparation of four novel indanyl carbanucleoside derivatives in the racemic form. The action of these compounds against hepatitis C virus was evaluated in vitro using the replicon cell line, Huh7.5 SG. Contrary to our expectations, all these compounds did not inhibit, but rather promoted HCV genotype 1b (HCVg1b) replication. Similar effects have been reported for morphine in the replicon cell lines, Huh7 and Huh8. Several biological experiments and computational studies were performed to elucidate the effect of these compounds on HCVg1b replication. Based on all the experiments performed, we propose that the increase in HCVg1b replication could be mediated, at least in part, by a similar mechanism to that of morphine on the enhancement of this replication. The presence of opioid receptors in Huh7.5 SG cells was indirectly determined for the first time in this work.
From simple organobromides or olefins to highly value-added bromohydrins: A versatile performance of dimethyl sulfoxide
Song, Song,Huang, Xiaoqiang,Liang, Yu-Feng,Tang, Conghui,Li, Xinwei,Jiao, Ning
, p. 2727 - 2731 (2015)
A novel and efficient direct transformation of secondary bromides or olefins to highly value-added bromohydrins has been disclosed. Dimethyl sulfoxide (DMSO), a cheap and common solvent, performs its versatile role as a solvent, an essential oxidant, and also as an oxygen source in this bromohydrin synthesis.
The absolute configuration of 2-bromo-2,3-dihydro-1H-inden-1-ols
Prysiazhnuk, Dmitry V.,Rusanov, Eduard B.,Kolodiazhnyi, Oleg I.
supporting information, p. 3023 - 3031 (2021/08/13)
All four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1H-inden-1-ols, which are important intermediates in the synthesis of biologically active compounds, were synthesized and their configurations were studied by enzymatic kinetic resoluti
Electrochemical bromofunctionalization of alkenes in a flow reactor
Seitz, Jakob,Wirth, Thomas
supporting information, p. 6892 - 6896 (2021/08/20)
The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.
Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides
Lee, Jeong Min,Bae, Dae Young,Park, Jin Yong,Jo, Hwi Yul,Lee, Eunsung,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 4608 - 4613 (2020/06/05)
A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.
Oxidative β-Halogenation of Alcohols: A Concise and Diastereoselective Approach to Halohydrins
Ai, Lingsheng,Wang, Weijin,Wei, Jialiang,Li, Qing,Song, Song,Jiao, Ning
, p. 437 - 441 (2019/02/26)
β-Halohydrins bearing transformable halo- and hydroxyl groups, are easily converted into various valuable blocks in organic and pharmaceutical synthesis. A diastereoselective β-halogenation of benzylic alcohols was achieved under simple and low-cost conditions, which provided a direct synthesis of β-halohydrins. The simple reaction conditions, easily available reagents, high diastereoselectivities, and additional oxidant-free make this reaction very attractive and practical.
Bromination of olefins with HBr and DMSO
Karki, Megha,Magolan, Jakob
, p. 3701 - 3707 (2015/04/22)
A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.
