1515-21-5

Basic information

• Product Name: (3aS,7aS)-3a,4,7,7a-tetrahydro-4,7-(epoxymethano)-2-benzofuran-1,3,8-trione
• CAS NO: 1515-21-5
• Molecular Formula: C₉H₆O₅
• Molecular Weight: 194.1409
• Mol File: 1515-21-5.mol

Chemical Properties

• Boiling Point: 506.1°C at 760 mmHg
• Flash Point: 235.2°C
• Density: 1.59g/cm³
• Vapor Pressure: 2.29E-10mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: (3aS,7aS)-3a,4,7,7a-tetrahydro-4,7-(epoxymethano)-2-benzofuran-1,3,8-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,7aS)-3a,4,7,7a-tetrahydro-4,7-(epoxymethano)-2-benzofuran-1,3,8-trione(1515-21-5)
• EPA Substance Registry System: (3aS,7aS)-3a,4,7,7a-tetrahydro-4,7-(epoxymethano)-2-benzofuran-1,3,8-trione(1515-21-5)

Safety Data

• Hazardous Substances Data: 1515-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3aS,7aS)-3a,4,7,7a-tetrahydro-4,7-(epoxymethano)-2-benzofuran-1,3,8-trione is used as a pharmaceutical candidate for [application reason] due to its unique molecular structure and reactivity. Its potential applications in this industry are still under investigation, and more research is needed to fully understand its properties and therapeutic potential.
Used in Materials Science:
In the field of materials science, (3aS,7aS)-3a,4,7,7a-tetrahydro-4,7-(epoxymethano)-2-benzofuran-1,3,8-trione is used as a component in the development of new materials for [application reason]. Its specific role and contribution to material properties are currently being explored, and further research is required to optimize its use in this field.

Upstream product

• 108-31-6 maleic anhydride 
• 504-31-4 pyran-2-one 

Downstream Products

• 82324-72-9 exo-6-(4-Methoxybenzyloxycarbonyl)-3-oxo-2-oxa-bicyclo<2.2.2>oct-7-en-exo-5-carbonsaeure 
• 82324-71-8 exo-6-(Benzyloxycarbonyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-exo-5-carbonsaeure 
• 82313-06-2 exo-5-(tert-Butoxycarbonylamino)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-exo-6-carbonsaeure-4-methoxybenzylester 
• 82324-73-0 exo-5-(tert-Butoxycarbonylamino)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-exo-6-carbonsaeure-benzylester 

Relevant articles and documents

Structural studies on α-pyrone cycloadducts. Manifestation of the early stages of CO2 extrusion by retro hetero-DielsAlder reaction

Structures of the -pyrone (pyran-2-one) cycloadducts 48 show deviations of some bond distances from their normal values, consistent with manifestation of the early stages of the retro hetero-DielsAlder decarboxylation reaction in the ground state structures. Thus the bridgehead CO(CO) and CCO(O) bonds are lengthened and the bridging CO bond is shortened. The degree of lengthening of the CO(CO) and CCO(O) bonds is similar, whereas in the calculated transition state structure there is significant asymmetry in the extent of CCO(O) and CO(CO) bond breaking. CSIRO 2009.

Diels-Alder Reactions with 2H-Pyran-2-ones: Reactivity and Selectivity

2H-Pyran-2-ones 1 react with maleic anhydride (2) in a double Diels-Alder reaction to give bicyclooct-2-ene-5,6:7,8-tetracarboxylic dianhydrides 5; the syn/syn structure was established.As expected, the reactivity of 1 was increased by electron donor substituents (OR, alkyl) and diminished by electron withdrawing substituents (CO2R).The steric influence of substituents at C-6 also decrease the reactivity of 1. - Methyl propiolate (6) and phenylacetylene (9) react with 1 to form the Diels-Alder products 7 which suffer CO2 elimination to yield methyl benzoates 8 with low and biphenyls 10 with high regioselectivity, respectively.

Synthesis of Some 3-Oxo-2-oxabicyclooct-7-ene Derivatives and Attempts of their Conversion into 3-Oxo-2-oxabicycloocta-5,7-diene

Acryloyl chloride, 2-chloroacrylonitrile, and fumaric ethyl ester chloride react at high pressure (5-10 kbar) with 2H-pyran-2-one to give 1:1 adducts.With maleic anhydride and fumaroyl dichloride purer products in higher yields are obtained at high pressure.The constitution and configuration of the products are determined in most cases.Starting with these compounds we have synthesized a large number of 3-oxo-2-oxabicyclooct-7-ene derivatives.Elimination experiments lead to the conclusion that 3-oxo-2-oxabicycloocta-5,7-diene (I) is not stable above 0 deg C.