38066-16-9Relevant academic research and scientific papers
Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D-π-A compounds
Mon?alves, Matias,Zanotto, Gabriel M.,Toldo, Josene M.,Rampon, Daniel S.,Schneider, Paulo H.,Gon?alves, Paulo F. B.,Rodembusch, Fabiano S.,Silveira, Claudio C.
, p. 8832 - 8842 (2017)
New vinyl sulfides and sulfoxides were obtained in good yields using the Horner-Wadsworth-Emmons (HWE) reaction. The vinyl sulfides and sulfoxides presented preferentially the E-stereochemistry. The respective vinyl sulfones were obtained in good yields from the vinyl sulfides by a simple oxidation step using mCPBA, solely as the E isomers. These derivatives presented absorption maxima in the UV-A region with molar absorptivity coefficients and radiative rate constant values ascribed to spin and symmetry-allowed 1π-π* electronic transitions. Experimentally, a small solvatochromic effect indicated an almost absent charge transfer character in the ground-state. A fluorescence emission in the violet-green region with a significative redshift on the maxima with increasing solvent polarity was observed, which could be related to a better electron delocalization in the excited state, as a result of an intramolecular charge transfer state. DFT and TD-DFT calculations were performed at the PBE1PBE and CAM-B3LYP levels of theory. No solvatochromic effect was observed in the ground state, but a bathochromic effect was detected in the emission maxima. Starting from sulfides to sulfones, the addition of oxygen atoms improved the charge separation, enabling an ICT state, mainly in P3 and P5. This charge separation was more efficient in the triphenylamino derivatives than among the pyrene derivatives since the first one has a better electron-donating character.
Organic material with high photoelectric property and preparation method thereof
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Paragraph 0058; 0066-0068, (2021/09/21)
The invention provides an organic material with high photoelectric property, wherein the organic material is a gem-cyclopentane benzothiophene compound, and can be applied to organic electronic devices. Organic light-emitting material and battery cathode material and the like. The structural general formula is as follows. In-flight C1 An aliphatic five-membered or six-membered ring, a geminally-substituted aliphatic five-membered or six-membered ring, or the like is absent. Ar1 Aryl or absent. Ar2 Aryl or absent. The invention provides a gem-cyclopentane-substituted benzothiophene compound with excellent performance, thereby solving the problem of starvation of organic small molecule photoelectric materials, and providing a simple and effective synthetic method for synthesizing substituted benzothiophene based on the novel material.
Synthesis of gem-Dimethylcyclopentane-Fused Arenes with Various Topologies via TBD-Mediated Dehydro-Diels-Alder Reaction
Zhang, Liyan,Jin, Tengda,Guo, Yingjie,Martin,Sun, Keju,Dudley, Gregory B.,Yang, Jingyue
, p. 16716 - 16724 (2021/11/16)
The development of efficient methods for the synthesis of substituted polycyclic arenes with various topologies is in high demand due to their excellent electrical and optical properties. In this work, a series of gem-dimethylcyclopentane-fused arenes with more than ten topologies were synthesized via a 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-mediated dehydro-Diels-Alder reaction with moderate to good yields. The introduction of the near-planar gem-dimethylcyclopentane moiety not only impacts the molecular conjugative system but also regulates the intermolecular π-πinteractions and crystal packing, which are critical for the photoelectric performance of arenes. The photophysical properties, molecular geometry, molecular packing of these compounds, and electrochemical properties were investigated by UV-vis absorption, fluorescence emission spectra, DFT calculations, single-crystal X-ray structure analysis, and cyclic voltammetry study.
Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection
Song, Zi-Long,Hou, Yanan,Bai, Feifei,Fang, Jianguo
, (2020/12/21)
Oxidative stress is constantly involved in the etiopathogenesis of an ever-widening range of neurodegenerative diseases. As a consequence, effective repression of cellular oxidative stress to a redox homeostatic condition is a promising and feasible strategy to treat, or at least retard the progression of, such disorders. Nrf2, a primary orchestrator of cellular antioxidant response machine, is responsible for detoxifying and compensating for deleterious oxidative stress via transcriptional activation of a diverse array of antioxidant biomolecules. In the framework of our persistent interest in disclosing small molecules that interfere with cellular redox-regulating machinery, we report herein the synthesis, optimization, and biological assessment of 47 vinyl sulfone scaffold-bearing small molecules, most of which exhibit robust neuroprotective effect against H2O2-mediated lesions to PC12 cells. After initial screening, the most potent neuroprotective compounds 9b and 9c with marginal cytotoxicity were selected for the follow-up studies. Our results demonstrate that their neuroprotective effects are attributed to the up-regulation of a panel of antioxidant genes and corresponding gene products. Further mechanistic studies indicate that Nrf2 is indispensable for the cellular performances of 9b and 9c, arising from the fact that silence of Nrf2 gene drastically nullifies their protective action. Taken together, 9b and 9c discovered in this work merit further development as neuroprotective candidates for the treatment of oxidative stress-mediated pathological conditions.
Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessinggem-P-containing methanes
Touqeer, Saad,Ielo, Laura,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 2425 - 2429 (2021/04/02)
The direct transfer of different α-substituted methyllithium reagents to chlorinated phosphorous electrophiles of diverse oxidation state (phosphates, phosphine oxides and phosphines) is proposed as an effective strategy to synthesize geminal P-containing
Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides
Collins, Niall,Connon, Robert,Evans, Paul,Sánchez-Sanz, Goar
supporting information, p. 6228 - 6235 (2020/10/02)
Reported is the construction, and facile base-mediated conversation of ten differently substituted 3-azido E-vinyl sulfones (γ-azido-α,β-unsaturated sulfones) into their isomeric vinyl azide counterparts. The requisite 3-azido E-vinyl sulfones were prepared from 3-bromo E-vinyl sulfones, which in turn were accessed from allyl sulfones via a bromination-elimination sequence. In relation to this a one-pot azidation-isomerisation sequence was developed which enabled the direct formation of the vinyl azides from the corresponding 3-bromo E-vinyl sulfones. Similarly, a convenient one-pot Horner–Wadsworth–Emmons olefination-isomerisation approach was utilised in order to prepare some of the allylic sulfones used in this study. The vinyl azide forming process typically proceeded with high levels of Z-selectivity, although this was dependent on the vinyl sulfone substitution pattern. Thus, with either no substituent or a methyl group in the γ- or β-position, relative to the sulfone, good, to high levels of Z-selectivity (Z/E = 85:15 to ≥ 95:5) were obtained. However, incorporation of an α-sulfonyl methyl substituent led to an E-selective process (Z/E = 20:80). A non-bonding interaction between the azido group and the α-sulfonyl vinylic proton is proposed, which acts as a conformational control mechanism to help guide the stereochemical outcome.
ISOTHIOCYANATE COMPOUND AND APPLICATION THEREOF
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Paragraph 0063; 0064, (2018/02/28)
The present invention provides an isothiocyanate compound and its application. The compound is an aryl-substituted isothiocyanate compound that has a structure of the general formula I. The isothiocyanate compound of the present invention has very good solubility in water, far better inhibitory activity for XPO1 protein than other non-aryl substituted congeneric compounds, little side effects, and good biological safety and bioavailability, and is quite suitable for clinical application. Therefore, the isothiocyanate compound would have tremendous potential market space and economic benefits.
Thermal Cycloisomerization of Putative Allenylpyridines for the Synthesis of Isoquinoline Derivatives
Morrison, Alec E.,Hrudka, Jeremy J.,Dudley, Gregory B.
supporting information, p. 4104 - 4107 (2016/08/30)
A cascade (cyclo)isomerization/elimination process produces novel isoquinoline derivatives of potential interest for pharmaceutical, biomedical, and energy-related research. Mechanistic experiments support a putative allenylpyridine (reminiscent of the Garratt-Braverman cyclization) as a key intermediate in the cascade process.
An Efficient Protecting-Group-Free Synthesis of Vinylic Sulfoximines via Horner-Wadsworth-Emmons Reaction
Chinthakindi, Praveen K.,Nandi, Ganesh Chandra,Govender, Thavendran,Kruger, Hendrik G.,Naicker, Tricia,Arvidsson, Per I.
supporting information, p. 1423 - 1427 (2016/05/24)
Herein, we report a convenient synthesis of aryl-substituted (E)-vinylic NH-sulfoximines via the Horner-Wadsworth-Emmons reaction without the use of protection-deprotection group strategies.
Wittig–Horner mediated synthesis of 4-vinyl sulfide derivatives of pyrazoles
Padilha, Gustavo,Kaufman, Teodoro S.,Silveira, Claudio C.
, p. 3349 - 3353 (2016/07/12)
The synthesis of a series of 4-vinyl sulfide derivatives of 1,3-diarylpyrazoles, including their corresponding sulfoxides and sulfones, is reported. Access to the target vinyl sulfides was stereoselectively achieved, in moderate to good yields, by the n-BuLi-mediated Wittig–Horner reaction of 4-formylpyrazoles with arylthiophosphonates and α-chloroarylthiophosphonates in dimethoxyethane. Their oxidation with H2O2in AcOH and mCPBA in CH2Cl2afforded satisfactory yields of the expected vinyl sulfoxides and vinyl sulfones, respectively. Enrichment in the more stable isomers during both oxidation processes was detected and a plausible general mechanistic explanation was given to these observations.
