17498-71-4Relevant academic research and scientific papers
Chromato-mass-spectrometric identification using partition coefficients in the system of hexane-2,2,2-Trifluoroethanol
Zenkevich
, p. 1391 - 1399 (2012)
An additional characteristic of organic compounds, the partition coefficients in the heterophase solvent system n-hexane-2,2,2-trifluoroethanol, is shown to be useful for refining the results of chromatographic and gas chromatography-mass spectrometric identification. This opportunity is the most important for compounds that were not yet characterized by either mass spectra or chromatographic retention indices. Pleiades Publishing, Ltd., 2012.
Contra-Thermodynamic Positional Isomerization of Olefins
Zhao, Kuo,Knowles, Robert R.
supporting information, p. 137 - 144 (2022/01/19)
A light-driven method for the contra-thermodynamic positional isomerization of olefins is described. In this work, stepwise PCET activation of a more substituted and more thermodynamically stable olefin substrate is mediated by an excited-state oxidant an
Electrochemical fluorosulfonylation of styrenes
Jiang, Yi-Min,Yu, Yi,Wu, Shao-Fen,Yan, Hong,Yuan, Yaofeng,Ye, Ke-Yin
supporting information, p. 11481 - 11484 (2021/11/16)
An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.
Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes
Jiang, Yimin,Shi, Zhaojiang,Wu, Jinnan,Wu, Shaofen,Ye, Keyin,Yu, Yi,Yuan, Yaofeng
supporting information, (2021/11/17)
Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.
Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy
Guo, Pan,Sun, Wangbin,Liu, Yu,Li, Yong-Xin,Loh, Teck-Peng,Jiang, Yaojia
supporting information, p. 5978 - 5983 (2020/08/05)
A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.
OPIOID RECEPTOR MODULATORS AND PRODUCTS AND METHODS RELATED THERETO
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Page/Page column 128-129, (2019/10/29)
Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, B, L, R3, R4, R5, R6, R8, m and n are as defined herein. Such compounds modulate the opioid receptor, particulare the mu-opioid receptor (MOR) and/or the kappa-opioid receptor (KOR), and/or the delta-opioid receptor (DOR). Products containing such compounds, as well as methods for their use and preparation, are also provided.
Copper-Catalyzed 1,2-Methoxy Methoxycarbonylation of Alkenes with Methyl Formate
Budai, Balázs,Leclair, Alexandre,Wang, Qian,Zhu, Jieping
supporting information, p. 10305 - 10309 (2019/06/27)
Reported here is a copper-catalyzed 1,2-methoxy methoxycarbonylation of alkenes by an unprecedented use of methyl formate as a source of both the methoxy and the methoxycarbonyl groups. This reaction transforms styrene and its derivatives into value-added β-methoxy alkanoates and cinnamates, as well as medicinally important five-membered heterocycles, such as functionalized tetrahydrofurans, γ-lactones, and pyrrolidines. A ternary β-diketiminato-CuI-styrene complex, fully characterized by NMR spectroscopy and X-ray crystallographic analysis, is capable of catalyzing the same transformation. These findings suggest that pre-coordination of electron-rich alkenes to copper might play an important role in accelerating the addition of nucleophilic radicals to electron-rich alkenes, and could have general implications in the design of novel radical-based transformations.
Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones
Chen, Jie,Guo, Pan,Zhang, Jianguo,Rong, Jiaxin,Sun, Wangbin,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 12674 - 12679 (2019/08/07)
An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.
Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes
Zhang, Liangliang,Oestreich, Martin
supporting information, p. 14304 - 14307 (2019/11/13)
A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C?Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes.
Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Ganiu, Moshood O.,Cleveland, Alexander H.,Paul, Jarrod L.,Kartika, Rendy
, p. 5611 - 5615 (2019/08/01)
The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.
