2.6- Dimethylphenyl ester

This stereoselectivity can be improved by use of a very bulky group. 2,6-Dimethylphenyl esters give F-enolates and anti aldol adducts.38... 

Phosphorohydrazidous acid, 2-[bis(2,6-dime thylphenoxy)phosphino]-1,2-dimethyl-, bis(2,6-dimethylphenyl) ester, 32 135-36... 

Paterson et al. achieved the convergent synthesis of the immunosuppressive agent discodermolide 205 by using a lithium-mediated aldol reaction with a chiral aldehyde (Scheme 8.31). The 2,6-dimethylphenyl ester 200 was derived to -enolate 201 by employing lithium 2,2,6,6-... 

SYNS 4-(DIMETHYLAMIN0)-3,5-DLMETHYLPHEN0L METHYLCARBAMATE (ESTER) 4-piMETHYL-amino)-3,5-dimethylphenyl ester, METHYLCARBAMIC ACID 4-piMETHYLAMINO)-3,5-DIMETHYLPHENYL-N-METHYLCARBAMATE 4-(DIMETHYLAMIN0)-3,5-XYLEN0L METHYLCARBAMATE (ESTER) 4-piMETHYLAMINO)-3,5-XYLYL ESTER... 

DIMETHYLPHENYL ESTER see ARQ600 BENZOIC ACID, 2-HYDROXY-, 4-(l,l-DIMETHYLETHYL)PHENYL ESTER see BSHIOO BENZOIC ACID, 2-HYDROXY-3,5-DINITRO-(9CI) see HKE600... 

Jackman, L. M., Petrei, M. M., and Smith, B. D. 1991. Degenerate transesterification of 3,5-dimethylphenolate/3,5-dimethylphenyl esters in weakly polar, aprotic solvents. Reactions of aggregates and complex-induced proximity effects. /. Am. Chem. Soc. 113 3451-3458. 

Synonyms 3-formyl-2,4-dihydroxy-5-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester atranoric acid Uses Component in extracts of oak moss used as fragrance Cross oak moss. PA A... 

C20H19O4P phosphoric acid diphenyl dimethylphenyl ester... 

The 3-(2-hydroxy-4,6-dimethylphenyl)-3-methylbutanoic acid shown in Fig. 8.23, as well as another phenylpropanoic derivative presented below, have been used as pro-moieties to prepare a number of prodrugs of therapeutic peptides [169] [238], Of interest here is that the pro-moiety is linked to the peptide by both amide and ester bonds to form a cyclic, double prodrug, the two-step activation of which is schematized in Fig. 8.24. Briefly, enzymatic hydrolysis of the ester bond unmasks a nucleophile (in this case, a phenol) that carries out an intramolecular attack on the amide bond, resulting in cy-clization of the pro-moiety and elimination of the peptide. [Leu5]enkephalin was one of the therapeutic peptides used to validate the concept, as illustrated in Fig. 8.25 [241],... 

Mepivacaine Mepivacaine is iV-(2,6-dimethylphenyl)-l-methyl-2-piperindincarboxam-ide (2.2.3). Two primary methods of synthesis have been suggested. According to the first, mepivacaine is synthesized by reacting the ethyl ester of l-methylpiperindine-2-carboxylic acid with 2,6-dimethylanilinomagnesium bromide, which is synthesized from 2,6-dimethylaniline and ethytmagnesium bromide [12-14]. 

A. 3,5-Dimethylphenyl 1-bromo-2-naphthoate (3). Under a nitrogen atmosphere, a 250-mL, oven-dried, round-bottomed flask containing anhydrous dichloromethane (100 mL) is charged with 1-bromo-2-naphthoic acid (1, 2.51 g, 10.0 mmol), 3,5-dimethylphenol (2, 1.23 g, 10.1 mmol), dicyclohexylcarbodiimide (DCC, 2.26 g. 11.0 mmol), and 4-(dimethylamino)pyridine (DMAP, 244 mg, 2.00 mmol) (Note 1). After the mixture is stirred for 12 hr at room temperature, the white precipitate that forms (Note 2) is discarded by filtration through a Buchner funnel. From the clear filtrate, the solvent is removed by rotary evaporation (35°C, 720 mbar, 540 mm) to give a colorless solid. RItration through a short silica gel column (5 x 40-cm column, silica gel 0.063 - 0.2 mm, 150 g eluent hexane / diethyl ether 5 1) delivers 3.35 g (94%) of the ester 3, which Is recrystallized from diethyl ether / hexane to give 3.28 g (92%) of a colorless solid (Note 3). 

Fishbein and McClelland examined the roles of ion pairs in the decomposition of 0-aroyl-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines (90, Scheme 42). These esters give rise to a nitrenium ion that has an estimated lifetime of ca. 0.25-0.50 ns based on the lifetime of 75m (1.5 ns) and an assumed 3- to 6-fold decrease in that lifetime caused by substituting NAc... 

C2H,N, Pyridine, 3,5-dimethyl-palladium complex, 26 210 CbHsNO, Benzoyl isocyanide chromium com-C HbO, Ethanone, 1-phenyl-manganese complex, 26 156-158 CBH, 02, Methyl benzoate chromium complex, 26 32 C H i, o-Xylylene magnesium complex, 26 147 ChH P, Phosphine, dimethylphenyl-iron complex, 26 61 ruthenium complex, 26 273 ChH12, 1,5-Cyclooctadiene iridium complex, 26 122 ruthenium complexes, 26 69-72, 253-256 ChH OjPS, 2-Butenedioic acid, 2-(dimethylphosphinothioyl)-dimethyl ester, manganese complex, 26 163... 

A three-component one-pot coupling of 2,6-dimethylphenyl isocyanide, methyl 2,4-dioxopentanoate and alkynoic esters leads to the isatin-like compounds (or fused pyrans) 20 (Scheme 5). The reaction proceeds by initial formation of the zwitterionic intermediate 21, which is protonated by methyl 2,4-dioxopentanoate. Attack of the newly generated nucleophile then forms the intermediate 22. The pyrrolidinone ring is formed upon loss of methanol and electrocyclization then occurs to afford the desired 2//-pyrans (Scheme 5) <2005S1049>. 

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