98922-98-6

Upstream product

• 3282-30-2 pivaloyl chloride 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 138459-91-3 3-pivaloyl-1,3-thiazolidine-2-thione 
• 67-56-1 methanol 
• 132540-70-6 C₁₂H₁₇NO₂ 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 1253778-81-2 N-(2-(benzyloxy)-4-methylphenyl)pivalamide 
• 1253778-79-8 N-(2-ethoxy-4-methylphenyl)pivalamide 
• 74510-47-7 {2-Chloro-3-methoxy-5-[2-methyl-2-(1-methyl-1H-imidazol-2-ylsulfanyl)-but-3-enyl]-phenyl}-methyl-carbamic acid methyl ester 
• 74510-51-3 {(E)-4-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-3-methyl-but-2-enyl}-phosphonic acid diethyl ester 
• 74510-50-2 [2-Chloro-5-((E)-4-iodo-2-methyl-but-2-enyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester 
• 74510-41-1 2-(2,2-Dimethyl-propionylamino)-3-methoxy-5-methyl-benzoic acid 
• 74510-46-6 (5-Bromomethyl-2-chloro-3-methoxy-phenyl)-methyl-carbamic acid methyl ester 
• 74510-45-5 (2-Chloro-3-methoxy-5-methyl-phenyl)-methyl-carbamic acid methyl ester 
• 74510-44-4 (2-Chloro-3-methoxy-5-methyl-phenyl)-carbamic acid methyl ester 
• 74510-43-3 2-Chloro-3-methoxy-5-methyl-benzoic acid 
• 90605-50-8 [5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester 
• 90605-47-3 [2-Chloro-5-((E)-4-hydroxy-2-methyl-but-2-enyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester 
• 80389-40-8 3-methoxy-5-methyl anthranilic acid 
• 869554-52-9 methyl 2-(2-benzenesulfonylvinyl)-3-methoxy-5-methylbenzoate 

Relevant academic research and scientific papers

Highly chemoselective acylation of substituted aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione

A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acetylated products 7 and 10a-h were prepared by treating the aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF in 70-100% yield. The esters 8 and 13d,b,j of 3- and 4-amino phenols could be obtained in 70-94% yield by treating with NaH and 1.

A brief and convergent synthetic route to defucogilvocarcin M chromophore: The formal synthesis of WS-5995 A and C

Densely substituted styryl sulfone 20 is shown to undergo double annulation with phthalide 21 to give, in one-pot operation and in excellent yield, the benzonaphthopyranone scaffold 22 of gilvocarcins.

Mechanism of the Reaction of Carbon and Nitrogen Nucleophiles with the Model Carcinogens O-Pivaloyl-TV-arylhydroxylamines: Competing SN2 Substitution and SN1 Solvolysis

The reaction of N,N-dimethylaniline (4) and aniline (5) with the O-pivaloyl-N-arylhydroxylamines 1a-f) in MeOH exhibits second-order kinetics and generates products of nucleophilic attack on the nitrogen of the hydroxylamine derivative. The characteristics of this reaction are not consistent with a nitrene or SET mechanism, an SN1 reaction with rate-limiting attack of the nucleophile, or nucleophile-assisted ionization. The only mechanism consistent with the available data, including substituent effects (ρ+ ≈ -3.0), cyclic voltammetry results, and product identifications, is an SN2 process. This reaction occurs in competition with an SN1 solvolysis that shows significant substituent dependence (ρ+ = -8.5). The reaction of 1 with 5 generates products of nucleophilic attack by both carbon (8, 9) and nitrogen (10). Competitive attack by carbon apparently occurs because of transition-state stabilization caused by the incipient C-N bond. The successful competition of the 8N2 reactions with SN1 solvolysis for the esters 1a and 1b, which are similar in reactivity to the putative carcinogens 2a-c, indicates that certain adducts isolated from in vivo experiments, including 3, may be formed via SN2 mechanisms.

Synthesis of maytansinoids: the aromatic moiety of maytansine

A simple and novel synthesis of the tetrasubstituted aromatic compound related to the "western-southern" region of maytansine has been achieved.