189329-48-4

Usage

Uses

Used in Organic Synthesis:
(1R,5S,6S,7R)-7-Benzenesulfonyl-6-bromo-6-phenylsulfanyl-bicyclo[3.1.1]heptane is used as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structural features make it a valuable building block for synthesizing a wide range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1R,5S,6S,7R)-7-Benzenesulfonyl-6-bromo-6-phenylsulfanyl-bicyclo[3.1.1]heptane is used as a starting material for the development of new pharmaceuticals. Its potential biological activities and structural diversity contribute to the design and synthesis of novel drug candidates.
Used in Agrochemical Development:
(1R,5S,6S,7R)-7-Benzenesulfonyl-6-bromo-6-phenylsulfanyl-bicyclo[3.1.1]heptane is also utilized in the development of agrochemicals. Its structural features and potential biological activities make it a promising candidate for the creation of new pesticides, herbicides, and other agricultural chemicals to improve crop protection and yield.

Upstream product

• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 2297-65-6 benzenesulfonyl bromide 

Downstream Products

• 189329-46-2 (1R,5S,7R)-7-Benzenesulfonyl-6,6-bis-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 189330-04-9 (1R,5S,6R,7S)-7-Benzenesulfonyl-6-methoxy-6-phenylsulfanyl-bicyclo[3.1.1]heptane 
• 189329-89-3 7-exo-(benzenesulfonyl)bicyclo[3.1.1]heptan-6-one 
• 189329-56-4 7-endo-(benzenesulfonyl)bicyclo[3.1.1]heptan-6-one 

Relevant academic research and scientific papers

Regio- and stereoselective addition of methane- and bromomethanesulfonyl bromides to 1-Phenylthiotricyclo[4.1.0.02,7]heptane

1-Phenylthiotricyclo[4.1.0.02,7]heptane reacted with MeSO 2Br and BrCH2SO2Br directly at mixing at 20°C in CH2Cl2 along a ionic (electrophilic with respect to bromine) mechanism affording a product of an anti-stereoselective addition to the central bicyclobutane C1-C7 bond of the norpinane structure. The reaction product contains the exo-oriented sulfonyl group in the geminal position to the SPh substituent. The structure of the adduct with MeSO2Br in a single crystal was determined by XRD analysis. Pleiades Publishing, Ltd., 2010.

Synthesis of Norpinane and Tricyclo[4.1.0.02,7]heptane Derivatives from 1-Phenylthiotricyclo[4.1.0.02,7]heptane

Radical addition of PhSO2Hlg (Hlg = Cl, Br) to 1-phenylthiotricyclo[4.1.0.02,7]heptane results in endo,syn-stereoselective splitting of the central bicyclobutane C1-C7 bond with formation of norpinane derivatives. The latter readily undergo substitution of the halogen by the action of nucleophiles (H2O, MeONa, PhSNa) and 1,3-dehydrohalogenation to 1-phenylsulfonyl-7-phenylthiotricyclo[4.1.0.02,7]heptane by the action of t-BuOK in THF. The stereoselective endo,syn addition of benzenesulfenyl chloride and benzeneselenol and also addition of benzenethiol in the presence of H2SO4 at the C1-C7 bond follows the Markownikoff rule. Acid-catalyzed hydration and bromohydroxylation with N-bromosuccinimide result in formation of 6-norpinanone derivatives.