55099-47-3Relevant academic research and scientific papers
Formal hydration of non-activated terminal olefins using tandem catalysts
Yang, Yongsheng,Guo, Jiayi,Ng, Huimin,Chen, Zhiyong,Teo, Peili
supporting information, p. 2608 - 2611 (2014/03/21)
The hydration of terminal olefins to secondary alcohols has been achieved using a Pd(ii)/Ru(ii) catalyst combination with high regioselectivity and yields. Both vinyl arenes and aliphatic olefins can be hydrated easily with the tandem catalyst system using a low catalyst loading of 1 mol%. The Royal Society of Chemistry 2014.
Candida antarctica lipase B-catalyzed synthesis of polyesters: Starting from ketones via a tandem BVO/ROP process
Zhong, Jiaren,Xu, Fan,Wang, Jianfeng,Li, Yanyan,Lin, Xianfu,Wu, Qi
, p. 8533 - 8540 (2014/03/21)
A novel enzymatic tandem procedure for the synthesis of substituted polyesters starting from ketones has been developed. Candida antarctica lipase B (CAL-B) was used as a catalyst for the whole procedure consisting of the Baeyer-Villiger oxidation (BVO) o
Progress toward the development of a safe and effective agent for treating reentrant cardiac arrhythmias: Synthesis and evaluation of ibutilide analogues with enhanced metabolic stability and diminished proarrhythmic potential
Hester,Gibson,Buchanan,Cimini,Clark,Emmert,Glavanovich,Imbordino,LeMay,McMillan,Perricone,Squires,Walters
, p. 1099 - 1115 (2007/10/03)
A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.
Antiarrhythmic (S)-enantiomers of methanesulfonamides
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, (2008/06/13)
Compounds of formula (I) and pharmacologically acceptable salts thereof wherein: n is 1 to 3, R is an alkyl, R1 is hydrogen or alkyl, R2 is alkyl, R3 is an alkyl; b) alkyl substituted with an aryl, heteroaryl or cycloalkyl
A practical method for alcohol oxidation with aqueous hydrogen peroxide under organic solvent- and halide-free conditions
Sato, Kazuhiko,Aoki, Masao,Takagi, Junko,Zimmermann, Klaus,Noyori, Ryoji
, p. 2287 - 2306 (2007/10/03)
A catalytic system consisting of sodium tungstate and methyltrioctylammonium hydrogensulfate effects oxidation of simple secondary alcohols to ketones using 3 - 30% H2O2 without any organic solvents. The oxidation can be conducted under entirely halide-free, mildly acidic conditions. A combination of tungstic acid and an appropriate quaternary ammonium salt also effects the alcohol dehydrogenation. The organic/aqueous biphasic reaction allows easy product/catalyst separation. The turnover number, defined as tools of product per mol of catalyst, approaches 77700 (2- octanol) or 179000 (1-phenylethanol), two orders of magnitude higher than any previously reported. Ester, alkyl and t-butyldimethylsilyl ether, epoxy, carbonyl, N-alkyl carboxamide, and nitrile groups are tolerated under the reaction conditions. Secondary alcohols are preferentially oxidized over terminal olefins. Primary alkanols are oxidized directly to carboxylic acids in a moderate to high yield. Benzylic alcohols are selectively oxidized to benzaldehydes or benzoic acids under suitable conditions. This method is high-yielding, clean, safe, operationally simple, and cost-effective, and therefore suitable for practical organic synthesis. The mechanistic origin of the catalytic efficiency is discussed.
Hydroxylation of prostanoids by fungi. Synthesis of (-)-15-deoxy-19-(R)-hydroxy-PGE1 and (-)-15-deoxy-18-(S)-hydroxy-PGE1
Holland,Brown,Chenchaiah,Rao
, p. 282 - 293 (2007/10/02)
A series of racemic substituted cyclopentanones, with alkyl groups corresponding to the upper prostanoid side chain and (or) the lower prostanoid side chain without the C-15 alcohol, has been synthesized. Using a steroid template for the prostanoid molecule as a basis for selection, fungi capable of hydroxylating steroids have been used to biotransform the prostanoid substrates. The predominant products were hydroxylated at the prostanoid C-18 and C-19 positions. The hydroxylations were enantioselective, with excesses in the range 10-60%, and in most cases the predominant configuration corresponded to that of the natural prostanoids. The sterochemistry of the C-19 hydroxyl group was found to be R by degradation of products to methyl 6-acetoxyheptanoate and comparison of that material with a resolved sample, obtained via crystallization of the brucine salt of ethyl 6-phthaloxyheptanoate. Hydroxylation at C-18 gave the S configuration of alcohol. Hydroxylation at prostanoid C-15 was observed, but in all cases this was accompanied by other reactions. Hydroxylation of Rhizopus arrhizus has been used in a preparation of (-)-15-deoxy-19-(R)-hydroxy-PGE1 and (-)-15-deoxy-18-(S)-hydroxy-PGE1.
