99295-72-4

Basic information

• Product Name: (-)-N,N-DICYCLOHEXYL-(1S)-ISOBORNEOL-10- SULFONAMIDE
• Synonyms: (1S)-(-)-Isoborneol-10-sulfonic dicyclohexylamide, (1S)-10-(N,N-Dicyclohexylsulfamoyl)isoborneol, 1R-exo-N,N-Dicyclohexyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptane-1-methanesulfonamide;(1S)-(-)-Isoborneol-10-sulfonic dicyclohexylamide, (1S)-10-(N,N-Dicyclohexylsulfamoyl)isoborneol, 1R-exo-N,N-Dicyclohexyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptane-1-methanesulfonamide, (-)-N,N-Dicyclohexyl-(1S)-isoborneol-10-sulfonamide
• CAS NO: 99295-72-4
• Molecular Formula: C₂₂H₃₉NO₃S
• Molecular Weight: 397.61
• Mol File: 99295-72-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 163-164 °C(lit.)
• Boiling Point: 520.4°Cat760mmHg
• Flash Point: 268.5°C
• Appearance: /
• Density: 1.16g/cm³
• Refractive Index: 1.557
• CAS DataBase Reference: (-)-N,N-DICYCLOHEXYL-(1S)-ISOBORNEOL-10- SULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-N,N-DICYCLOHEXYL-(1S)-ISOBORNEOL-10- SULFONAMIDE(99295-72-4)
• EPA Substance Registry System: (-)-N,N-DICYCLOHEXYL-(1S)-ISOBORNEOL-10- SULFONAMIDE(99295-72-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 99295-72-4(Hazardous Substances Data)

Usage

General Description

(-)-N,N-Dicyclohexyl-(1S)-isoborneol-10-sulfonamide is a chiral compound with a sulfonamide functional group. It is a derivative of isoborneol, a bicyclic terpene alcohol, and is commonly used as a chiral auxiliary in asymmetric synthesis to control the stereochemistry of reactions. The dicyclohexyl and sulfonamide groups provide steric hindrance and protect the isoborneol backbone, allowing for selective reactions at specific positions. (-)-N,N-DICYCLOHEXYL-(1S)-ISOBORNEOL-10- SULFONAMIDE has been used in various organic reactions and has shown to be an effective and versatile chiral auxiliary in synthetic chemistry.

InChI:InChI=1/C22H39NO3S/c1-21(2)17-13-14-22(21,20(24)15-17)16-27(25,26)23(18-9-5-3-6-10-18)19-11-7-4-8-12-19/h17-20,24H,3-16H2,1-2H3/t17-,20-,22-/m1/s1

Upstream product

• 104-94-9 4-methoxy-aniline 
• 104926-27-4 N,N-Dicyclohexyl-C-[(1R,2S,4S)-7,7-dimethyl-2-((E)-1-trimethylsilanyloxy-dec-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 
• 96864-09-4 Decanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-19-2 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-14-7 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-16-9 (S)-2-(4-Methoxy-benzylamino)-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-27-2 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104926-28-5 (R)-2-Bromo-decanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 

Downstream Products

• 172477-07-5 (1R,2S,4S)-(+)-1-dicyclohexylsulfamoylmethyl-7,7-dimethylbicyclo<2.2.1>hept-2-yl hexadecanoate 
• 439589-15-8 (S)-2-Benzyloxycarbonylamino-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-14-7 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-26-1 (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-24-9 (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 888034-68-2 (+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-(3-(2,4,6-trimethylphenyl)isoxazole-4-carboxy)bicyclo[2.2.1]heptane-1-methanesulfonamide 
• 888034-75-1 (+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-(5-methyl-3-(2,4,6-trimethylphenyl)isoxazole-4-carboxy)bicyclo[2.2.1]heptane-1-methanesulfonamide 
• 130157-15-2 (R)-2-(Benzhydrylidene-amino)-4-chloro-pent-4-enoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130157-15-2 (S)-2-(Benzhydrylidene-amino)-4-chloro-pent-4-enoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130157-08-3 (R)-2-(Benzhydrylidene-amino)-4-methyl-pent-4-enoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130157-08-3 (S)-2-(Benzhydrylidene-amino)-4-methyl-pent-4-enoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130157-00-5 (Benzhydrylidene-amino)-acetic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130195-81-2 Azido-acetic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 130178-50-6 Amino-acetic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant articles and documents

General approach for the stereocontrolled construction of the beta-lactam ring in amino acid-derived 4-alkyl-4-carboxy-2-azetidinones.

The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N(alpha)-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).

Asymmetric α-Acetoxylation of Carboxylic Esters

Using the readily accessible chiral auxiliaries 1-3 the sulfonamide-shielded O-silylated esters 5 underwent ?-face-selective α-acetoxylation on successive treatment with Pb(OAc)4 and NEt3*HF to give after recrystallization α-acetoxy ester 6 in 55-66percen