13351-26-3

Usage

Uses

Used in Organic Synthesis:
5,9-Methano-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-one is used as a key intermediate in organic synthesis for the construction of complex organic molecules. Its unique structure allows for various chemical reactions, facilitating the synthesis of a wide range of compounds with potential applications in different fields.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 5,9-Methano-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-one is utilized as a building block for the development of new drugs. Its structural features and reactivity make it a promising candidate for the design of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Chemical Research and Development:
5,9-Methano-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-one is employed as a subject of study in chemical research to explore its properties, reactivity, and potential applications. Its complex molecular structure and diverse reactivity offer opportunities for the discovery of new chemical reactions and the development of innovative synthetic methods, contributing to the advancement of the field.
Used in the Production of Specialty Chemicals:
5,9-Methano-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-one is used as a precursor in the synthesis of specialty chemicals, which are high-value compounds with unique properties and applications. Its role in the production of these chemicals is crucial for meeting the demands of various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in the Development of Advanced Materials:
5,9-Methano-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-one is also utilized in the development of advanced materials with specific properties, such as high thermal stability, unique optical characteristics, or enhanced mechanical strength. Its incorporation into these materials can lead to the creation of innovative products with applications in various sectors, including electronics, aerospace, and automotive industries.

InChI:InChI=1/C12H12O/c13-10-6-8-5-9(7-10)12-4-2-1-3-11(8)12/h1-4,8-9H,5-7H2

Upstream product

• 13351-27-4 3-chlorobenzo<6,7>bicyclo<3.2.1>octa-2,6-diene 
• 13351-25-2 1-(2-chloro-allyl)-1H-indene 
• 5471-63-6 1,3-diphenylisobenzofuran 
• 22099-66-7 10-bromotricyclo[6.3.1.0^2,7]dodeca-2,4,6,9-tetraene 
• 483306-09-8 3-(ortho-styryl)cyclobutanone 
• 95-13-6 1-indene 
• 22099-66-7 3-bromo-6,7-benzobicyclo<3.2.1>octa-2,6-diene 
• 89229-03-8 3-tert-butoxy-6,7-benzobicyclo<3.2.1>octa-2,6-diene 
• 4889-50-3 7-oxo-7H-benzocycloheptene-6,8-dicarboxylic acid diethyl ester 
• 117404-71-4 (1RS,2RS,5RS)-2,3-dibromo-6,7-benzobicyclo<3.2.1>octa-3,6-diene 
• 10136-84-2 1-indenylmagnesium bromide 
• 91-14-5 1,2-divinylbenzene 

Downstream Products

• 15391-62-5 benzo<6,7>bicyclo<3.2.1>octa-6-diene 
• 29784-42-7 6,8-Bis-[1-phenyl-meth-(Z)-ylidene]-5,6,8,9-tetrahydro-5,9-methano-benzocyclohepten-7-one 
• 24309-43-1 Tricyclo<6.3.1.0^2,7>dodeca-2,4,6,9-tetraen 
• 24309-43-1 (1S(R),8S(R))-tricyclo[6.3.1.0^2,7]dodeca-2,4,6,9-tetraene 
• 66720-21-6 7-exo-Phenyl-5,9-methano-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-endo-ol 

Relevant academic research and scientific papers

BICYCLIC ALLENES: GENERATION AND TRAPPING OF 6,7-BENZOBICYCLOOCTA-2,3-DIENE

Treatment of 3-bromo-6,7-benzobicycloocta-2,3-diene (9) with potassium tert.-butoxide produces the strained bicyclic allene (10) which is trapped by 1,3-diphenylbenzofuran (DBI) to give five isomeric cycloadducts.In the absence of DBI, allene (10) gave rise to enol ether (18) by addition of tert.-butanol.

Cooperative activation of cyclobutanones and olefins leads to bridged ring systems by a catalytic [4 + 2] coupling

Bridged ring systems are widely found in natural products, and successful syntheses of them frequently feature intramolecular Diels-Alder reactions. These reactions are subclassified as either type I or type II depending on how the diene motif is tethered to the rest of the substrate (type I are tethered at the 1-position of the diene and type II at the 2-position). Although the type I reaction has been used with great success, the molecular scaffolds accessible by the type II reactions are limited by the strain inherent in the formation of an sp2 carbon at a bridgehead position. Here, we describe a complementary approach that provides access to these structures through the C-C activation of cyclobutanones and their coupling with olefins. Various alkenes have been coupled with cyclobutanones to provide a range of bridged skeletons. The ketone group of the products serves as a convenient handle for downstream functionalization.

Catalyzed intramolecular olefin insertion into a carbon-carbon single bond

Intramolecular insertion of a C-C double bond into a C-C single bond was achieved by treatment of cyclobutanone bearing an o-styryl group at the 3-position with a catalytic amount of a cationic rhodium(I)-dppp complex. Initially, rhodium is inserted betwe

Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins

Herein, we report an intramolecular rhodium-catalyzed decarbonylative coupling between cyclobutanones and alkenes that proceeds by C?C activation and provides a distinct approach to a diverse range of saturated bridged cyclopentane derivatives. In this reaction, cyclobutanones serve as cyclopropane surrogates, reacting in a formal (4+2?1) transformation. To demonstrate the efficacy of this method, it was applied in a concise synthesis of the antifungal drug Tolciclate.

Bridged aromatic alkenes for the study of carbocation-π interaction

Toward the goal of gaining further insight into carbocation-π interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit π complexation of an intramolecular tertiary carbocation with a benzene ring, but