122-35-0Relevant articles and documents
Synthesis process of 2-phenoxypropionyl chloride
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Paragraph 0030, (2018/05/16)
The invention discloses a synthesis process of 2-phenoxypropionyl chloride. The synthesis process comprises the following steps: (1) under conditions of water and alkali, by taking phenol and 2-chloropropionic acid as raw materials, carrying out reaction, adding acid at the end of the reaction to adjust the pH till the solution is in a faintly acid state, and carrying out suction filtering to obtain 2-phenoxypropionic acid; (2) dissolving the 2-phenoxypropionic acid in an organic solvent, adding an acyl chlorinating agent for reaction, removing the organic solvent at the end of the reaction, and collecting a fraction with temperature of 80 DEG C, so as to obtain the 2-phenoxypropionyl chloride, wherein a mole ratio of the phenol to the 2-chloropropionic acid is 1 to 1.2-1.5; a mole ratio of the phenol and the alkali is 1 to 1.2-5.0; a mole ratio of solid powder a and the acyl chlorinating agent is 1 to 1.2-2.0. The method disclosed by the invention is easy to operate; selected reactionconditions are mild (0 to 80 DEG C); selected reagents are readily available; the amount of waste gas, wastewater and solid wastes is small; the synthesis process is environmentally friendly and lowin harm to a human body.
Synthesis and Caco-2 cell permeability of N-substituted anthranilamide esters as ADP inhibitor in platelets
Kim, Sohee,Shin, Beom Soo,Ma, Eunsook
, p. 1147 - 1156 (2015/02/19)
Twelve N-substituted anthranilamide esters (1-5, 8, 9, 12, 13, and 15-17) were synthesized and evaluated for their ability to inhibit the in vitro aggregation by washed human platelets induced by adenosine 5′-diphosphate (10 μM). The antiplatelet activity of DL-n-butyl 5-hydroxy-N-(2-phenoxypropionyl)anthranilate (9, IC50 = 10.5 μM) was most active among the tested compounds and ethyl ester 8 (IC50 = 11.2 μM) showed the second most activity. DL-Ethyl and DL-n-butyl 5-(p-toluenesulfonyloxy)-N-(2-phenoxypropionyl)anthranilate (12, IC50 = 13.1 μM and 13, IC50 = 14.0 μM), DL-methyl N-(2-phenoxybutyryl)anthranilate (2, IC50 = 12.7 μM), DL-N-(2-phenoxypropionyl)anthranilic acid (5, IC50 = 13.7 μM) displayed lower antiplatelet activity than 8 and 9. Compound 5 was more active than methyl ester prodrug 1. n-Butyl 5-hydroxy-N-(4′-acetoxybenzoyl)anthranilate (15, IC50 = 28.3 μM) showed moderate activity. Compounds 1 (IC50 = 42.8 μM), 4 (IC50 = 56.7 μM), 16 (IC50 = 51.0 μM), and 17 (IC50 = 49.8 μM) exhibited low antiplatelet activity. Methyl N-phenoxyacetylanthranilate (3, IC50 = 78.0 μM) showed the lowest antiplatelet activity. The compounds with branched alkyl chain (2 and 5) were more active than compounds with straight chain (3 and 4). The apparent permeability coefficient (Papp, cm/s) values of compounds 2 and 9 were determined as 45.34 ± 4.67 and 33.17 ± 5.15 × 10-6 cm/s by Caco-2 cell permeability assay.
Base-catalyzed bifunctional addition to amides and imides at low temperature. A new pathway for carbonyl hydrogenation
John, Jeremy M.,Takebayashi, Satoshi,Dabral, Nupur,Miskolzie, Mark,Bergens, Steven H.
supporting information, p. 8578 - 8584 (2013/07/27)
Mono- or dideprotonation at the N-H groups of the Noyori ketone hydrogenation catalyst trans-[RuH2((R)-BINAP)((R,R)-dpen)] (1a) yields trans-M[RuH2((R,R)-HNCH(Ph)CH(Ph)NH2)((R)-BINAP)], where M = K+(8-K) or Li+ (8-Li), or trans-M 2[RuH2((R,R)-HNCH(Ph)CH(Ph)NH)((R)-BINAP)], where M = Li+ (8-M′2), which have unprecedented activity toward the hydrogenation of amide and imide carbonyls at low temperatures in THF-d8. Details of the origins of the enantioselection for the desymmetrization of meso-cyclic imides by hydrogenation with 8-K are also described herein.
