87420-26-6

Basic information

• Product Name: (1R,2S,3R)-(+)-3-[N-(BENZENESULFONYL)-N-(3,5-DIMETHYL-PHENYL)AMINO]-2-BORNANOL
• Synonyms: (1R,EXO,EXO)-3-[N-(3,5-DIMETHYLPHENYL)-BENZENESULFONAMIDO]ISOBORNEOL;(1R,2S,3R)-(+)-3-[N-(BENZENESULFONYL)-N-(3,5-DIMETHYL-PHENYL)AMINO]-2-BORNANOL;(1R)-3-[n-(3,5-dimethylphenyl)benzenesul fonamido]isoborneol;(1R,2S,3R)-(+)-3-(N-benzenesulfonyl-N-(3,5 -dimet;(1R,2S,3R)-(+)-3-(N-BENZENESULFONYL-N-(3 ,5 -DIMETHYLPHENYL)AMINO)-2-BORNANOL, 99;(1R-exo,exo)-3-(N-(3,5-Dimethylphenyl)benzenesulfonamido)
• CAS NO: 87420-26-6
• Molecular Formula: C₂₄H₃₁NO₃S
• Molecular Weight: 413.57
• Mol File: 87420-26-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 122-125 °C(lit.)
• Boiling Point: 560.3°Cat760mmHg
• Flash Point: 292.6°C
• Appearance: /
• Density: 1.212g/cm³
• Vapor Pressure: 2.17E-13mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: (1R,2S,3R)-(+)-3-[N-(BENZENESULFONYL)-N-(3,5-DIMETHYL-PHENYL)AMINO]-2-BORNANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3R)-(+)-3-[N-(BENZENESULFONYL)-N-(3,5-DIMETHYL-PHENYL)AMINO]-2-BORNANOL(87420-26-6)
• EPA Substance Registry System: (1R,2S,3R)-(+)-3-[N-(BENZENESULFONYL)-N-(3,5-DIMETHYL-PHENYL)AMINO]-2-BORNANOL(87420-26-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 87420-26-6(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1R,2S,3R)-(+)-3-[N-(benzenesulfonyl)-N-(3,5-dimethyl-phenyl)amino]-2-bornanol" is a chiral molecule that consists of a bornane skeleton with a sulfonamide group and an amino group substituted at the 3-position. It is commonly used in organic synthesis and medicinal chemistry as a reagent for asymmetric synthesis and as a chiral auxiliary. The compound's stereochemistry and functional groups make it a versatile building block in the preparation of biologically active molecules and pharmaceutical intermediates. Its specific arrangement of atoms allows for selective interactions with biological targets, making it of interest for drug development and chemical research.

InChI:InChI=1/C24H31NO3S/c1-16-13-17(2)15-18(14-16)25(29(27,28)19-9-7-6-8-10-19)21-20-11-12-24(5,22(21)26)23(20,3)4/h6-10,13-15,20-22,26H,11-12H2,1-5H3

Upstream product

• 104282-56-6 Chloro-acetic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 102834-10-6 (E)-But-2-enoic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 263710-60-7 C₂₈⁽¹³⁾CH₃₉NO₄S 
• 170211-89-9 (1R,2S,3R,4S)-<3--2-bornyl>-(6R)-2-hydroxy-6-phenyl-cyclohexenecarboxylate 
• 170211-88-8 (1R,2S,3R,4S)-<3--2-bornyl>-(6R)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate 
• 170117-09-6 (S)-6-Butyl-2-hydroxy-cyclohex-1-enecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 170211-85-5 (R)-6-tert-Butyl-2-hydroxy-cyclohex-1-enecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 170211-87-7 (1R,2S,3R,4S)-<3--2-bornyl>-(6R)-2-hydroxy-6-vinyl-cyclohexenecarboxylate 
• 67-56-1 methanol 
• 170211-91-3 (S)-2-Hydroxy-6-methyl-cyclohex-1-enecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 87360-00-7 (1R,4S)-3-[(E)-3,5-Dimethyl-phenylimino]-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 98-09-9 benzenesulfonyl chloride 
• 102917-45-3 (S)-4,4,4-Trichloro-3-methyl-butyric acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

Downstream Products

• 108781-57-3 Pentanedioic acid bis-{(1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl} ester 
• 76529-59-4 Propionic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 105961-38-4 (1'R)-3'-exo--2'-exo-bornyl 3-phenylpropionate 
• 263710-60-7 C₂₈⁽¹³⁾CH₃₉NO₄S 
• 104530-13-4 (S)-1,4,4-Trimethyl-2-oxo-cyclopentanecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104476-85-9 (R)-1,4,4-Trimethyl-2-oxo-cyclopentanecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104282-48-6 (Z)-4-Methyl-pent-2-enoic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 108781-61-9 2-Hydroxy-2-methyl-3-phenyl-propionic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 108781-58-4 (S)-2-Hydroxy-propionic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 87420-17-5 (S)-2-Methyl-3-phenyl-propionic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 172926-53-3 (1R,2S,3R,4S)-<3--2-bornyl>-(1S*)-2-oxo-1-phenylselenyl-cyclohexenecarboxylate 
• 172926-51-1 (1R,2S,3R,4S)-<3--2-bornyl>-(1R*)-2-oxo-1-phenylselenyl-cyclohexenecarboxylate 
• 172926-64-6 (1R,2S,3R,4S)-<3--2-bornyl>-(1R,6S)-6-butyl-2-oxo-cyclohexanecarboxylate 
• 172926-65-7 (1R,2S,3R,4S)-<3--2-bornyl>-(1R,6S)-6-tert-butyl-2-oxo-cyclohexanecarboxylate 

Relevant articles and documents

Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group

Three approaches to the synthesis of L-leucine selectively labelled with carbon-13 or deuterium in either diastereotopic methyl group as well as at C-3 and C-4 are described. In all three methods the stereogenic centre at C-2 was created with total stereocontrol via a one-pot, two-enzyme catalysed procedure involving hydrolysis and reductive amination of a 2-keto ester. However, the approaches vary in the synthesis of the isotopically labelled 2-keto esters and in the production of the stereogenic centre at C-4 which was achieved either via alkylation of a propionylated Evans' auxiliary with labelled iodomethane or by the diastereoselective conjugate addition of a labelled organocopper reagent to crotonate tethered to a chiral sultam. The latter approach proved most efficient and using the (1R,2S, 3R)-3-[N-phenylsulfonyl-N-(3,5-dimethyldiphenyl)aminobornan-2-ol ester 27, [5-13C]-L-leucine was prepared with >98% de at C-4 and in 49% overall yield from the first labelled intermediate 28.

SYNTHESIS OF ENANTIOMERICALLY PURE (S)-3-TRICHLOROMETHYLBUTYRIC ACID VIA ASYMMETRIC CONJUGATE ADDITION OF TRICHLOROMETHYL METAL COMPOUNDS TO A CHIRAL ENOATE. ACTIVATION EFFECT OF A SULFONYLAMINO GROUP.

(+)(S)-3-Trichloromethylbutyric acid, a building block for synthesis of various marine natural products, can be prepared via 99:1 stereoselective conjugate addition of Cl3CMgCl to the crotonate of a chiral auxiliary containing a sulfonylamino substituent.

INFLUENCE OF CATION COMPLEXING SOLVENT ADDITIVES AND FUNCTIONAL GROUPS IN ASYMMETRIC ALKYLATIONS OF ESTERS VIA LITHIUM ENOLATES

Highly diastereoselective alkylations of propionates of chiral alcohols derived from (+)-camphor are described.It is demonstrated that steric shielding as well as cation complexation are important for stereoselection.The latter effects are in part rationa