76665-83-3Relevant academic research and scientific papers
Highly enantioselective conjugate addition of thioglycolate to chalcones catalyzed by lanthanum: Low catalyst loading and remarkable chiral amplification
Hui, Yonghai,Jiang, Jun,Wang, Wentao,Chen, Weiliang,Cai, Yunfei,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
supporting information; experimental part, p. 4290 - 4293 (2010/08/19)
(Figure Presented) Ramping it up: The titled reaction has been developed using a chiral N, N′-dioxide-LaIII complex as the catalyst. The reaction proceeded with high yield and enantioselectivity, Remarkably, a high asymmetric amplification was observed, as 98% ee was achieved using 1 mol% L/ La(OTf)3 in which the ee value of L was 2% ee. Tf= trifluoromethanesulfonyl.
2-Arylthiomorpholine derivatives as potent and selective monoamine oxidase B inhibitors
Lühr, Susan,Vilches-Herrera, Marcelo,Fierro, Angélica,Ramsay, Rona R.,Edmondson, Dale E.,Reyes-Parada, Miguel,Cassels, Bruce K.,Iturriaga-Vásquez, Patricio
experimental part, p. 1388 - 1395 (2010/05/17)
2-Arylthiomorpholine and 2-arylthiomorpholin-5-one derivatives, designed as rigid and/or non-basic phenylethylamine analogues, were evaluated as rat and human monoamine oxidase inhibitors. Molecular docking provided insight into the binding mode of these inhibitors and rationalized their different potencies. Making the phenylethylamine scaffold rigid by fixing the amine chain in an extended six-membered ring conformation increased MAO-B (but not MAO-A) inhibitory activity relative to the more flexible α-methylated derivative. The presence of a basic nitrogen atom is not a prerequisite in either MAO-A or MAO-B. The best Ki values were in the 10-8 M range, with selectivities towards human MAO-B exceeding 2000-fold.
Pesticidal and parasiticidal use of 1-aryl-1-(substituted thio, sulfinyl and sulfonyl)-2-nitroethane compounds
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, (2008/06/13)
The present invention relates to the pesticidal use of 1-aryl-1-(substituted thio, sulfinyl and sulfonyl)-2-nitroethane compounds having the structural formula I
Kinetics of Reversible Thiolate Ion Addition to Substituted β-Nitrostyrenes in Water. Radicaloid Transition State or Principle of Nonperfect Synchronization?
Bernasconi, Claude F.,Schuck, David F.
, p. 2365 - 2373 (2007/10/02)
The kinetics of reversible nucleophilic thiolate ion (RS- with R = n-Bu, HOCH2CH2, MeO2CCH2CH2 and MeO2CCH2) addition to Z-substituted β-nitrostyrenes (Z = 4-Me2N, 4-MeO, 4-MeS, 4-Me, H, 3-Cl, 4-Cl, 3-CN, 4-CN, and 3-NO2), to form ArCH(RS)CH=NO2-, have been measured in water at 20 deg C.Rate constants in the forward (k1) and reverse direction (k-1) and equilibrium constants (K1) correlate reasonably well with Hammett ?-constants for the non-?-donor substituents but show deviations for the ?-donors 4-Me2N, 4-MeO, and 4-MeS.These deviations are negativefor K1 but positive for k1 and k-1; the positive deviations for the ?-donor substituents are also observed when plotting log k1 vs log K1 (Broensted plots).The negative deviations of K1 are a consequence of resonance stabilization of the olefin.The positive deviations are attributed to a transition-state stabilization stemming from a preorganization created by the ?-donor which leads to a better delocalization of the negative charge into the nitro group.An alternative interpretation of the rate acceleration in terms of a radicaloid transition state (Gross, Z.; Hoz, S.J.Am.Chem.Soc. 1988, 110, 7489) cannot be ruled out but is shown to be less attractive and unnecessary.Broensted parameters such as βnuc, βeq, βnnuc, and βnlg, and intrinsic rate constants (k0 = k1 = k-1 when K1 = 1) were determined from the dependence on the RS- basicity for β-nitrostyrene and 3-cyano-β-nitrostyrene. βeq is low (0.5), indicating that the carbon basicity of RS- is less sensitive to electronic effects in R than its proton basicity. βnuc (βnnuc) is very low, suggesting a transition state withvery little C-S bond formation.The low βnnuc (0.22) contrasts with a large αnnuc = d log k1/d log K1 = 0.74 (variation of Z), indicating a large transition-state imbalance (αnnuc - βnnuc), as previously observed in the reaction of RS- with α-nitrostilbenes.The intrinsic rate constant (log k0 = 3.5) is also similar to that for the reaction of RS- with α-nitrostilbenes and significantly higher than for the reaction of amines with β-nitrostyrenes.Most of these features can, at least in part, be attributed to the soft acid-soft base interactions of RS- with the nitroolefins.Rate constants for carbon protonation of several of the ArCH(RS)CH=NO2- adducts by acetic acid (kHAp were also determined.They display the unusual, but for nitronate ions typical, acceleration when Ar and/or R is made more electron withdrawing.
