14309-54-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2098, 1986 DOI: 10.1021/jo00361a031

InChI:InChI=1/C10H12O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-4H,5-6H2,1-2H3

Upstream product

• 106-99-0 buta-1,3-diene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 5680-13-7 dimethyl 3-vinyl-1,2-dichlorocyclobutane-1,2-dicarboxylate 
• 67969-82-8 tetrafluoroboric acid diethyl ether 
• 314082-92-3 [Os(k1-OC(O)CH₃)(-C=CHCH₂C(CO₂Me)=C(CO₂Me)CH₂-)(CO)2(P(i-Pr)3)2] 
• 18668-68-3 4-bromo-buta-1,2-diene 
• 4773-89-1 1,4-cyclohexadiene-1,2-dicarboxylic anhydride 
• 6012-81-3 (1S,2R)-1,2-Dichloro-3-vinyl-cyclobutane-1,2-dicarboxylic acid 
• 101774-07-6 dimethyl 3-vinylcyclobutene-1,2-dicarboxylate 
• 77-79-2 3-Sulfolene 
• 186581-53-3 diazomethane 
• 610-13-9 cyclohexa-1,4-diene-1,2-dicarboxylic acid 

Downstream Products

• 90295-61-7 (±)-dimethyl cyclohexa-2,4-diene-1,2-dicarboxylate 
• 4336-19-0 1,2-dimethyl cyclohex-1-ene-1,2-dicarboxylate 
• 4773-89-1 1,4-cyclohexadiene-1,2-dicarboxylic anhydride 
• 610-11-7 2,4-cyclohexadiene-1,2-dicarboxylic acid 
• 1515-23-7 cyclohexa-2,5-diene-1,2-dicarboxylic acid 
• 65774-75-6 1,2-bis(hydroxymethyl)-3,6-dihydrobenzene 

Relevant academic research and scientific papers

METHOD OF RETARDING AN ETHYLENE RESPONSE

A compound of Formula I, wherein R1, R2, R3, R4, R5 and R6 are independently hydrogen, halogen, an unsubstituted alkyl, alkenyl, alkynyl, cydoalkyi, cydoalkylalkyi, aryl, phenyl, or naphthyl group, and a substituted alkyl, alkenyl, alkynyl, cydoalkyi, cydoalkylalkyi, aryl, phenyl, or naphthyl group having as a substituent a halogen, alkoxy, substituted phenoxy, unsubstituted phenoxy group or a heteroatom such as oxygen, sulfur, nitrogen, phosphorus and boron.

PYRIDAZINONE-BASED BROAD SPECTRUM ANTI-INFLUENZA INHIBITORS

The present invention relates to compounds of formula (I): (I) or pharmaceutically acceptable salts thereof, as well as processes for their manufacture, pharmaceutical compositions comprising them, and their use as medicaments.

Tandem Diels-Alder/cross-coupling reactions of generated in situ organoindium reagents in a one-pot process

[Chemical equation presented] Tandem Diels-Alder/ cross-coupling reactions with organoindium reagents generated in situ from 1-bromo-2,3-butadiene and indium were developed in a one-pot process. [4 + 2] Cycloaddition reactions using organoindium reagents and subsequent Pd-catalyzed cross-coupling reactions provided the rapid synthesis of six-membered carbocycles starting from 1-bromo-2,3-butadiene.

The dihydride-osmium(IV) complex [OsH2(/c2-O2CCH3)(H2O)(PiPr3)2]BF4 as a precursor for carbon-carbon coupling reactions

The dihydride-osmium(IV) complex [OsH2(/c2-O2CCH3)(H2O)(PiPr3)2]BF4 (1) reacts with acetylene (1 atm) at 0 °C to give polyacetylene and the vinyl-carbyne derivative [Os(CH= CH2)(2-02CCH3)(=CCH3)(PiPr3)2]BF4 (2). Both polyacetylene and 2 can also be obtained by reaction of [OsH(K2-O2CCH3XCCH3XPiPr3)2]BF4 (3) with acetylene. Under an acetylene atmosphere, complex 2 yields polyacetylene in a slow but constant manner. Complex 2 reacts with carbon monoxide to give initially the carbene derivative [Os(/t2-O2CCH3){=C(CH= CH2)CH3}(CO)(PiPr3)2]BF4 (4), by migratory insertion of the carbyne ligand of 2 into the Os-vinyl bond. Under a carbon monoxide atmosphere, complex 2 is unstable and evolves into [Os(K2-O2CCH3)(CO)2(PiPr3)2]BF4 (5). Treatment of 2 with KOH in methanol produces the deprotonation of the carbyne ligand and the formation of the vinyl-vinylidene derivative Os(CH=CH2)(/c2-O2CCH3)(=C=CH2)(PiPr3)2 (6), which reacts with carbon monoxide to give the butadienyl compound Os{C(CH=CH2)=CH2}{1-OC(O)CH3}(CO)2(PiPr3)2 (7) by migratory insertion of the vinylidene ligand into the Os-vinyl bond. The structure of 7 has been determined by X-ray diffraction analysis. The geometry around the osmium atom can be rationalized as a distorted octahedron with the phosphine ligands occupying opposite positions. The remaining perpendicular plane is formed by the butadienyl ligand, the acetate, and the carbonyl groups mutually cis disposed. The Os-butadienyl distance is 2.195(5) A, whereas the torsion angle in the diene is 50.7(8)°. The butadienyl ligand of 7 acts as a diene in Diels-Alder reactions. Thus, the addition of dimethyl acetylenedicarboxylate and maleic anhydride to benzene solutions of 7 affords the corresponding cycloaddition products Os-{C=CHCH2C(CO2Me)=C(C02Me)CH2{1-OC(O)CH3}(CO)2(PiPr3)2 (8) and Os{C=CHCH2CH-[C(O)OC(0)]CHCH2}{1-OC(O)CH3}(CO)2(PiPr3)2 (9). Treatment of 8 with HBF4-OEt2 gives i 5 and dimethyl l,4-cyclohexadiene-l,2-dicarboxylate.

The Nickel Promoted 1,3-Migration of an sp2 Center: Ring Expansion of a Vinylcyclobutene

The nickel tetracarbonyl promoted rearrangement if dimethyl 3-vinyl-1,2-dichlorocyclobutane-1,2-dicarboxylate (1) to dimethyl 1,4-cyclohexadiene-1,2-dicarboxylate (2) proceeds in two distinct steps involving dimethyl 3-vinylcyclobutene-1,2-dicarboxylate (

A CYCLOPENTANE, CYCLOPENTENE AND CYCLOPENTANONE ANNULATION METHODOLOGY

The chemistry derived from the dienolates of 1,2-dicarboxylic acid esters is described.New methods for preparing cyclopentane, cyclopentene and cyclopentanone rings affixed to the diesters are discussed.