6265-30-1

Basic information

• Product Name: 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)-
• CAS NO: 6265-30-1
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.176
• Mol File: 6265-30-1.mol

Chemical Properties

• Boiling Point: 362.1°Cat760mmHg
• Flash Point: 177.1°C
• Density: 1.339g/cm³
• CAS DataBase Reference: 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)-(6265-30-1)
• EPA Substance Registry System: 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)-(6265-30-1)

Safety Data

• Hazardous Substances Data: 6265-30-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)is utilized as a key component in pharmaceutical research and drug development. Its unique chemical structure suggests potential applications as a therapeutic agent, which could be harnessed to address various medical conditions. 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)-'s properties are currently under investigation to determine its full range of therapeutic capabilities and safety profiles.
Used in the Development of New Materials:
Beyond its pharmaceutical applications, 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)may also find use in the development of new materials. Its cyclic structure and chemical properties could contribute to the creation of innovative materials with unique characteristics, potentially useful in various industrial applications.
Used as a Chemical Intermediate in Organic Synthesis:
In the realm of organic synthesis, 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)serves as a valuable chemical intermediate. Its reactivity and structural features make it a candidate for use in the synthesis of more complex organic compounds, which could have applications in a wide range of industries, including pharmaceuticals, agrochemicals, and materials science.
Further research is necessary to explore the full potential of 3a,4,7,7a-Tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione (3aalpha,4alpha,7alpha,7aalpha)-, including additional applications and benefits that may arise from its unique chemical properties. As our understanding of this compound grows, so too may the scope of its practical uses in various fields.

Upstream product

• 541-59-3 maleiimide 
• 542-92-7 cyclopenta-1,3-diene 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 42867-30-1 Silver maleimide 
• 61800-55-3 endo-5-carbamoylbicyclo[2.2.1]hept-2-ene-endo-6-carboxylic acid 

Downstream Products

• 5263-68-3 (1α,2α,6α,7α)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene 
• 936747-84-1 C₃₃H₃₂O₃N₂ 
• 78028-14-5 N-chloroacetyl-4-azatricyclo<5.2.1.0^2,6>dec-8-ene 
• 78087-47-5 (1S,2R,6S,7R)-4-Benzenesulfonyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene 
• 1187583-61-4 C₂₃H₂₈ClN₃O₂ 
• 1187583-62-5 C₂₃H₂₈ClN₃O₂ 
• 1187583-63-6 C₂₄H₃₁N₃O₂ 
• 1187583-64-7 C₂₄H₃₁N₃O₂ 
• 1187583-60-3 4-[4-(4-phenylpiperazin-1-yl)butyl]-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione 

Relevant articles and documents

Alicyclophanes: A new range of cyclophanes containing rigid alicyclic subunits in place of the aromatic rings

Norbornenosuccinimides have been coupled stereoselectively with 2,5- bis(trifluoromethyl-1,3,4-oxadiazole to prepare alicyclic scaffolds 5 and 20. Alkylations of the terminal succinimido-nitrogens of 5 with bis-alkylating agents have produced macrocyclic compounds in a short, high-yielding procedure. Alicyclophanes containing one scaffold subunit were obtained from 1,6-dibromohexane, 1,5-dichloro-3-oxapentane, 1,11-dibromo-3,6,9- trioxaundecane and 9,10-bis(chloromethyl)anthracene. Larger alicyclophanes incorporating two spacer subunits were formed by intermolecular cyclisation of 5 with 1,2-dibromoethane or 19 with m- or p-xylylene dibromide. Reaction of 5 with propargyl bromide, followed by oxidative coupling (CuCl) of the pendant acetylenes provided bis-acetylenic alicyclophane 13. (C) 2000 Elsevier Science Ltd.

Pyrrolidine synthesis on polystyrene supports: Development of a 'one-pot' dipolar cycloaddition strategy

Preparation of substituted pyrrolidines was achieved by solid-phase synthesis via a room temperature 1,3-dipolar cycloaddition of a silver-azomethine ylide, generated in situ, with a polymer-supported maleimide.

Inverse electron-demand Diels-Alder (iEDDA) bioorthogonal conjugation of half-sandwich transition metallocarbonyl entities to a model protein

Novel transition metallocarbonyl complexes carrying a norbornene or an oxanorbornene group were synthesized by [4 + 2] cycloaddition between the organometallic maleimide dienophiles and cyclopentadiene or furan, respectively. The oxanorbornene adduct was obtained as a mixture of endo and exo isomers as confirmed by X-ray diffraction and NMR spectroscopy. The (oxa)norbornene groups further provided convenient chemical reporters to carry out inverse electron demand Diels-Alder (iEDDA) reactions with tetrazine derivatives. Detailed kinetic studies with a model tetrazine revealed that faster rates of reaction were determined with both isomers of the oxanorbornene complex with respect to the norbornene complexes. Eventually, incorporation of metallocarbonyl entities into bovine serum albumin equipped with tetrazine handles was achieved as shown by IR spectroscopy of the protein conjugates.

IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts reactions

The first o-iodoxybenzoic acid (IBX) mediated oxidation of unactivated amines to imines is described. A range of meso-pyrrolidines were shown to be suitable substrates. The chemical space was further explored with one-pot oxidative Ugi-type and aza-Friedel-Crafts reactions, which proved to be highly diastereoselective.

PROCESS FOR THE INDUSTRIAL SYNTHESIS OF LURASIDONE

Disclosed is a process for the industrial synthesis of Lurasidone from (1R,2R)-cyclohexane-1,2-diyldimethanol (1), 3-(piperazin-1- yl)benzo[d]isothiazole (3) and (3aR,4R,7R,7aS)-3a,4,7,7a-tetrahydro-4,7- methanoisobenzofuran-1,3-dione (6).). Said process is optimised to obtain Lurasidone with high yields and high purities by preparing highly pure synthesis intermediates, using critical raw materials and reagents in amounts close to the stoichiometric amounts, increasing productivity and reducing the costs and environmental impact of the process.

Quinoline-functionalized norbornene for fluorescence recognition of metal ions

A quinoline-functionalized norbornene (1) and its homopolymer (P1) for metal ions recognition have been synthesized and characterized. In CH3CN solution, 1 exhibited fluorescence enhancement response toward Hg2+, Zn2+ and Cu2+, with Hg2+ resulting in a green emission at 465 nm, and Zn2+/Cu2+ increasing 1's original emission at 406 nm. NMR titrations and DFT calculations results indicated that 1 bound Hg2+ in an imidic acid tautomeric form of the amide quinoline receptor, while Zn2+ and Cu2+ were bound to 1 in an amide tautomeric form. In addition, owing to the strong imidic acid tautomeric binding mode of 1-Hg2+ complex, 1 can recognized Hg2+ from Zn2+/Cu2+ and other competitive metal ions. In contrast, the homopolymer P1, which was obtained by ring opening metathesis polymerization (ROMP) method, exhibited only fluorescence enhancement sensing to Hg2+ and Cu2+ in an amide tautomeric binding mode with increasing emission at 416 nm.

Synthesis of [1]benzothieno[3,2-b][1]benzothiophene pendant and norbornene random co-polymers via ring opening metathesis

2-Octyl-7-(11-(cis-5-norbornene-endo-2,3-dicarboxylicimide)undecane)[1] benzothienopheno[3,2-b] benzothienophene (1) was synthesised and co-polymerised with varying amounts of 1-decyl(cis-5-norbornene-endo-2,3-dicarboxylic) imide (2) or norbornene, using a ruthenium catalyst, to produce a series of random co-polymers.

AMIDOALKYLPIPERAZINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES

The invention relates to novel amidoalkylpiperazinyl derivatives of tricyclic heterocyclic systems of general formula (I), wherein Z represents -NH- and X represents -S-, or Z represents -S- and X represents >C=C1 represents H or -CH3, R6 and R7 both represent H, n is an integer from 0 to 4 inclusive, G represents a cyclic amide or imide moiety, and optical isomers, geometric isomers, and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of the central nervous system disorders.

Mechanochemical Diels-Alder cycloaddition reactions for straightforward synthesis of endo-norbornene derivatives

Under mechanochemical milling conditions, Diels-Alder cycloaddition of cyclopentadiene with maleic anhydride and maleimide derivatives proceeded very smoothly, affording endo-norbornenes exclusively in quantitative yield. All the transformations were accomplished at room temperature without using any catalyst or organic solvent, thus the workup and purification procedure is very simple. Control experiments on traditional and other tentative conditions were also investigated. Georg Thieme Verlag Stuttgart - New York.

Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.