20607-85-6

Usage

InChI:InChI=1/C8H12O2/c1-8(2,3)6-5-7(9)10-4/h1-4H3

Upstream product

• 67-56-1 methanol 
• 52418-50-5 4,4-dimethyl-2-pentynoic acid 
• 51067-54-0 Diazo(1,2,3-tri-tert-butyl-2-cyclopropen-1-yl)essigsaeure-methylester 
• 79-22-1 methyl chloroformate 
• 917-92-0 3,3-Dimethylbut-1-yne 

Downstream Products

• 27331-01-7 Methyl 2-tert.-butyl-1,4-cyclohexadien-1-carboxylat 
• 27330-99-0 2-tert.-Butyl-1-cyclohexen-1-carbonsaeure 
• 27331-00-6 Methyl 2-tert.-butyl-1-cyclohexen-1-carboxylat 
• 27392-15-0 cis-2-tert.-Butylcyclohexancarbonsaeure 
• 27392-15-0 trans-2-tert.-Butylcyclohexancarbonsaeure 
• 133189-66-9 trimethyl 2,4,6-tri(1,1-dimethylethyl)benzene-1,3,5-tricarboxylate 
• 52888-72-9 5-(tert-butyl)-2-hydroxybenzoic acid methyl ester 

Relevant academic research and scientific papers

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

Hydrostannylation-cross-coupling strategy for the stereoselective synthesis of alkylidenemalonates and related α,β-unsaturated esters

A method for the stereoselective synthesis of alkylidenemalonates and related α,β-unsaturated esters by a hydrostannylation-cross-coupling process has been developed. Pd-catalyzed and radical hydrostannylation of propiolate derivatives stereoselectively provided α-alkoxycarbonyl (E)- and (Z)-vinylstannanes, respectively, which were then converted into alkylidenemalonates by the Stille coupling reaction. A one-pot process was also realizable for the Pd-catalyzed reactions.

Regio- and stereoselective synthesis of 2,3,5-trienoates by palladium-catalyzed alkoxycarbonylation of conjugated enyne carbonates

Palladium-catalyzed carbonylation of 2,4-enyne carbonates in an alcohol and under balloon pressure of CO proceeds through 1,5-substitution to yield (E)-2,3,5-trienoates. The olefin geometry of the substrate is important to control the overall stereochemistry of this alkoxycarbonylation method. The reaction proceeds through successive formation of π-allylpalladium with an R3 group oriented syn and σ-allenyl palladium complexes.

Platinum-catalyzed hydrosilylations of internal alkynes: Harnessing substituent effects to achieve high regioselectivity

Rule of thumb: The high yielding title reaction is described with a focus on understanding the factors that govern the regioselectivity of the process (see scheme). Electronic, steric, and functional group properties all influence the selectivity, an understanding of which allows the selective formation of trisubstituted vinylsilanes, which are synthetically useful compounds for accessing stereodefined alkenes. Copyright

COMPETITIVE REARRANGEMENTS. I. NEOPENTYLIC VERSUS SKELETAL BICYCLOOCTANE -> BICYCLOOCTANE REARRANGEMENTS

Generation of a carbenium ion common to two systems which are able to undergo either a skeletal bicyclooctane --> bicyclooctane rearrangement or a neopentylic rearrangement conducts only to the latter reaction. Thus, 8-carbomethoxy-7-t-butyl-dibenzobicyclooctatriene (15) reacts with strong acids or bromine, yielding neopentyl rearranged products 17, respectively 21. Reaction mechanisms are proposed.

Carbenes, 28. tert-Butyl 2,3,4-Tri-tert-butylcyclobutadiene-1-carboxylate

The cyclopropenyldiazoacetate 3a - available from tri-tert-butylcyclopropenylium bromide (1) and the mercury bis(diazoacetate) 2a - is the starting material for the synthesis of the title compound 5a.The carbene 4a, generated photolytically from 3a, is responsible for the formation of both the cyclobutadiene 5a and the acetylenes 6 and 7a.Acetylene formation is also observed in the flash pyrolysis of 3a (formation of 6, 7a, 8, and 9) and 5a (formation of 6, 8, and 9).The extremely air sensitive cyclobutadiene 5a ( -> 16) shows a pronounced cycloaddition behaviour towards dienophiles.With dimethyl ac etylenedicarboxylate, maleic anhydride, cyclopentadiene, diethyl azodicarboxylate and 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts were isolated (17, 18, 19, 20, 21).The series of the diazadihydro Dewar benzenes is also entered by the reaction of the cyclopropenyldiazoacetates 3 with the triazolinedione; the betaines 22 and 24 are regarded to be intermediates of this reaction.