86537-30-6

Basic information

• Product Name: Bicyclo[1.1.0]butane, 1-[(4-methylphenyl)sulfonyl]-
• CAS NO: 86537-30-6
• Molecular Formula: C11H12O2S
• Molecular Weight: 208.281
• Mol File: 86537-30-6.mol

Chemical Properties

• CAS DataBase Reference: Bicyclo[1.1.0]butane, 1-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[1.1.0]butane, 1-[(4-methylphenyl)sulfonyl]-(86537-30-6)
• EPA Substance Registry System: Bicyclo[1.1.0]butane, 1-[(4-methylphenyl)sulfonyl]-(86537-30-6)

Safety Data

• Hazardous Substances Data: 86537-30-6(Hazardous Substances Data)

Upstream product

• 17482-19-8 1-(but-3-en-1-ylsulfonyl)-4-methylbenzene 
• 141642-40-2 (2-tosylcyclopropyl)methyl methanesulfonate 
• 141642-38-8 1-mesyloxymethyl-1-phenylsulfonylmethylcyclopropane 

Downstream Products

• 96667-28-6 Methanesulfonic acid 2-[3-(toluene-4-sulfonyl)-bicyclo[1.1.0]but-1-yl]-ethyl ester 
• 96667-27-5 2-[3-(Toluene-4-sulfonyl)-bicyclo[1.1.0]but-1-yl]-ethanol 
• 86537-37-3 1-(3-Isopropenyl-cyclobutanesulfonyl)-4-methyl-benzene 
• 86537-38-4 1-(3-Isopropenyl-cyclobutanesulfonyl)-4-methyl-benzene 
• 96667-34-4 2-[3-(Toluene-4-sulfonyl)-cyclobutyl]-propan-2-ol 
• 96667-33-3 1-(3-Allyl-cyclobutanesulfonyl)-4-methyl-benzene 
• 96667-29-7 3-(1-methylethenyl)-1-(p-tolylsulfonyl)bicyclo<1.1.0>butane 
• 96667-44-6 1-(3,3-Dimethyl-cyclobutanesulfonyl)-4-methyl-benzene 
• 96667-45-7 1-(3-Allyl-3-methyl-cyclobutanesulfonyl)-4-methyl-benzene 
• 96667-41-3 1-isopropylidene-3-(p-tolylsulfonyl)cyclobutane 
• 96667-75-3 [3-Isopropenyl-1-(toluene-4-sulfonyl)-cyclobutyl]-methanol 
• 86537-32-8 1-(3-Butyl-cyclobutanesulfonyl)-4-methyl-benzene 
• 96667-54-8 1-Methyl-4-(3-phenylsulfanyl-cyclobutanesulfonyl)-benzene 
• 96667-53-7 1-Methyl-4-(3-phenylsulfanyl-cyclobutanesulfonyl)-benzene 

Relevant articles and documents

DISULFIDE BIOCONJUGATION

Compounds and methods are provided for one-step functionalization of disulfide bonds in proteins.

Organic chemistry: Strain-release amination

To optimize drug candidates, modern medicinal chemists are increasingly turning to an unconventional structural motif: small, strained ring systems. However, the difficulty of introducing substituents such as bicyclo[1.1.1]pentanes, azetidines, or cyclobutanes often outweighs the challenge of synthesizing the parent scaffold itself. Thus, there is an urgent need for general methods to rapidly and directly append such groups onto core scaffolds. Here we report a general strategy to harness the embedded potential energy of effectively spring-loaded C-C and C-N bonds with the most oft-encountered nucleophiles in pharmaceutical chemistry, amines. Strain-release amination can diversify a range of substrates with a multitude of desirable bioisosteres at both the early and late stages of a synthesis. The technique has also been applied to peptide labeling and bioconjugation.

The Strain Limit in Intramolecular Nucleophilic Substitution

Kinetics and products of reactions of sulfonyl-stabilised carbanions bearing ω-leaving groups have been examined.The intention was to explore the upper limit of strain that can be tolerated for intramolecular nucleophilic substitution in these systems and

Strain-induced Mechanism Change: the Limit of Strain Tolerance in Intramolecular Nucleophilic Substitution?

The limit of strain energy differential for intramolecular nucleophilic substitution via a sulfonyl-stabilised carbanion to give cyclopropane analogues in hydroxylic solvents is around 160 kJ mol-1; above this level, concerted, albeit unactivat