817201-06-2

Upstream product

• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 

Downstream Products

• 130156-82-0 (1R*,2R*,3S*,4S*)-2,3-bis(benzyloxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene 
• 1227078-72-9 (1R*,2R*,3S*,4S*)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diylbis(methylene) dibenzoate 
• 1267636-00-9 (1R,2R,8S,9S)-4,6,12-trioxa-5,5-diphenyl-5-silatricyclo[7,2,1,0(2,8)]undec-10-ene 
• 139928-66-8 2,3-bis(benzoylthiomethyl)-7-oxabicyclo<2.2.1>hept-5-ene 

Relevant academic research and scientific papers

Molecular design of biologically active compounds based on platelet activating factor (PAF): 7-Oxabicyclo[2.2.1]heptane system as a strong antagonist of PAF

7-Oxabicyclo[2.2.1]heptane system was designed based on the PAF structure. Among four stereoisomers synthesized, the diexo derivative turned out to be a new and strong antagonist of PAF.

Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles

Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.

ANTICANCER AGENTS AND PROCESS OF MAKING THEREOF

Provided herein are compositions and processes of making of anticancer compounds useful for cancer treatments. These cyclohexenone compounds show an unexpected result against certain cancer cells compared to their known analogs.

Method for Preparing Curable Bicyclic Compound Derived from Biomass

The present invention relates to a curable bicyclic compound derived from biomass, solvent-free curable composition and a method for preparing thereof. The curable compound derived from biomass according to the invention comprises a bicycle structure, to which one of two epoxide functional groups are bonded.

Synthesis of thermally degradable epoxy adhesives

We have developed a new strategy for the synthesis of epoxide-containing polymers where the pendant reactive groups are connected to the main backbone via thermally labile oxonorbornene groups. The polymers were synthesized by radical 1,4-polymerization of the appropriate bicyclic diene monomer. The produced polymers can be crosslinked in the presence of a diamine and de-crosslinked by thermal treatment at 160 °C, which induces retro-Diels-Alder reaction and cleaves pendant groups from the polymer backbone, as confirmed by differential scanning calorimetry. The potential for the utilization of this polymer as a thermally removable adhesive was demonstrated by a simple adhesion test. This method provides access to thermally cleavable epoxy networks that can be quickly and irreversibly disintegrated into nonvolatile components upon heating to a specified temperature. Copyright

Convenient synthesis of meso-cyclohexa-1,3-dienes by one-pot two-step deoxygenation of 7-oxabicyclo[2.2.1]hept-2-enes

Iron(III) hydroxide oxide was found to be an efficient catalyst for the ring-opening reaction of 5,6-cis-disubstituted 7-oxabicyclo[2.2.1]hept-2-enes with acetyl bromide in dichloromethane at room temperature to give cyclohexene derivatives with leaving groups (acetoxy or bromo groups) disposed on each allylic position. A successive one-pot treatment of the reaction mixture with zinc powder and tetrahydrofuran successfully induced reductive 1,4-elimination to afford synthetically useful 5,6-disubstituted mesocyclohexa-1,3-dienes in good-to-high yields. Georg Thieme Verlag Stuttgart.

Copper-catalysed meso-bislactone ring opening using Grignard and mixed triorganozinc reagents

An efficient copper-mediated SN2′ ring-opening reaction of a meso-bislactone has been developed using Grignard reagents and, for the first time, mixed triorganozinc reagents.

Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo-[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2- ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.

An Investigation of the Retro Diels-Alder Reaction as a Method for the Generation of Diatomic Sulfur

The cyclic disulfides 2,3-dithiabicyclooct-5-ene 5, 1,4-dihydro-2,3-benzodithin 6 and hexahydro-5,8-epoxy-2,3-benzodithiin 7 have been prepared by oxidation of the corresponding dithiols.Each of these compounds has been subjected to vapour phase pyrolysis in order to determine whether a retro Diels-Alder reaction occurs, leading to the formation of diatomic sulfur (S2) and a diene.Compounds 5 and 7 both appeared to decompose in this way; in each case the expected diene was detected in the pyrolysate together with sulfur (S8).Attempts to intercept S2 and thus to obtain direct evidence for its formation were not successful.The benzodithiin 6 underwent an analogous loss of sulfur on vapour phase pyrolysis, but only as a minor reaction pathway, and this decomposition pathway was not detectable in solution pyrolyses.Solution pyrolysis of 6 in the presence of N-phenylmaleinimide gave N-phenyl-2,3-naphthalimide 21 in low yield. cis-Cyclopentene-3,5-dithiol 9 has also been prepared but no evidence could be obtained for the formation of disulfide 4 on oxidation.Reaction of the dithiol 9 with aldehydes and ketones in the presence of acids led to the formation of adducts (such as 12 and 13 from acetone) which were rapidly interconverted in acidic media.

Synthesis and Pharmacological Evaluation of 5,6-exo-Epoxy-7-oxabicycloheptane Derivatives

-7-hept-2-yl>-5-heptenoic acid (31) and -7--7-oxabicyclohept-2-yl>-5-heptenoic acid (37) were found to be selective TxA2 antagonists at the platelet and pulmonary thromboxane receptors.An efficient stereospecific synthesis of these compounds and a series of structural analogues is described.Compounds 31 and 37 both inhibited the bronchoconstriction induced by arachidonic acid in the anesthetized guinea pig.