14381-41-0

Usage

Uses

Used in Pharmaceutical Industry:
Benzocyclobutyl-1-carboxylic acid is used as a dynamic building block for the synthesis of complex pharmaceutical compounds. Its ability to undergo Diels-Alder reactions allows for the creation of large and selective molecules, such as cyclohexylmethylpiperidinyltriphenylpropioamide, which is a highly selective M3 antagonist. This application is significant in the development of new drugs targeting specific receptors, potentially leading to more effective treatments for various medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, Benzocyclobutyl-1-carboxylic acid serves as a key intermediate for the production of various organic compounds. Its unique structure and reactivity make it an attractive candidate for use in the synthesis of novel molecules with potential applications in different industries, such as materials science, agrochemicals, and specialty chemicals.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 2257, 1958 DOI: 10.1021/ja01542a055Tetrahedron Letters, 23, p. 3665, 1982 DOI: 10.1016/S0040-4039(00)88652-9

InChI:InChI=1/C9H8O2/c10-9(11)8-5-6-3-1-2-4-7(6)8/h1-4,8H,5H2,(H,10,11)

Upstream product

• 1775-23-1 2-diazo-indan-1-one 
• 35095-07-9 Methyl bicyclo<4.2.0>octa-1,3,5-triene-7-carboxylate 
• 83-33-0 inden-1-one 
• 612-12-4 o-Xylylene dichloride 
• 60973-59-3 α,α-dichloro-o-xylene 
• 15028-10-1 indan-1,2-dione-2-oxime 
• 7315-17-5 3-(2-chloro-phenyl)-propionitrile 
• 35447-99-5 1,2-dihydrobenzocyclobuten-1-ol 
• 21120-91-2 1-bromobenzocyclobutene 
• 1069114-67-5 dimethyl cyclobutabenzene-1,1(2H)-dicarboxylate 
• 118-92-3 anthranilic acid 
• 6809-91-2 1-cyanobenzocyclobutane 
• 124-38-9 carbon dioxide 
• 61599-88-0 1-chloro-1,2-dihydrobenzocyclobutene 

Downstream Products

• 61599-85-7 bicyclo[4.2.0]octa-1,3,5-trien-7-amine 
• 1473-47-8 Benzocyclobuten-1-carbonsaeure-chlorid 
• 15100-35-3 Bicyclo<4.2.0>octa-1,3,5-triene-7-methanol 
• 1459789-79-7 N-(2-bromophenyl)-N-methyl-1,2-dihydrocyclobutabenzene-1-carboxamide 
• 1471-89-2 bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Synthesis of benzocyclobutenes by palladium-catalyzed C-H activation of methyl groups: Method and mechanistic study

An efficient catalytic system has been developed for the synthesis of benzocyclobutenes by C-H activation of methyl groups. The optimal conditions employed a combination of Pd(OAc)2 and PtBu3 as catalyst, K2CO3 as the base, and DMF as solvent. A variety of substituted BCB were obtained under these conditions with yields in the 44-92% range, including molecules that are hardly accessible by other methods. The reaction was found limited to substrates bearing a quaternary benzylic carbon, but benzocyclobutenes bearing a tertiary benzylic carbon could be obtained indirectly from diesters by decarboxylation. Reaction substrates bearing a small substituent para to bromine gave an unexpected regioisomer that likely arose from a 1,4-palladium migration process. The formation of this "abnormal" regioisomer could be suppressed by introducing a larger subsituent para to bromine. DFT(B3PW91) calculations on the reaction of 2-bromo-tert-butylbenzene with Pd(PtBu3) with different bases (acetate, bicarbonate, carbonate) showed the critical influence of the coordination mode of the base to induce both an easy C-H activation and to allow for a pathway for 1,4-palladium migration. Carbonate is shown to be more efficient than the two other bases because it can abstract the proton easily and at the same time maintain κ1-coordination without extensive electronic reorganization.

Ramoplanin derivatives possessing antibacterial activity

Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

A Novel Method for the Synthesis of Methyl Indane-1-carboxylates by Ring Contraction of Tetralones Using Lead(IV) Acetate

A smooth ring contraction of the tetralones takes place with lead(IV) acetate in presence of boron trifluoride etherate and methanol to afford methyl indane-1-carboxylates in satisfactory yields.The method is extended to five- and seven-membered cyclic aromatic ketones.

FORMATION OF SUBSTITUTED BENZOCYCLOBUTENES THROUGH FLASH VACUUM PYROLYSIS

Benzocyclobutenes carrying a substituent in the four membered ring are obtained in high yield from 2-methyl benzaldehydes through a reaction sequence involving a pyrolitic 1,4-elimination of HCl in the crucial step.