96303-89-8

Basic information

• Product Name: 2-exo-acryloyloxy-N,N-dicyclohexylbornane-10-sulfonamide
• Synonyms: 2-exo-acryloyloxy-N,N-dicyclohexylbornane-10-sulfonamide
• CAS NO: 96303-89-8
• Molecular Weight: 451.671
• Mol File: 96303-89-8.mol

Chemical Properties

• CAS DataBase Reference: 2-exo-acryloyloxy-N,N-dicyclohexylbornane-10-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-exo-acryloyloxy-N,N-dicyclohexylbornane-10-sulfonamide(96303-89-8)
• EPA Substance Registry System: 2-exo-acryloyloxy-N,N-dicyclohexylbornane-10-sulfonamide(96303-89-8)

Safety Data

• Hazardous Substances Data: 96303-89-8(Hazardous Substances Data)

Upstream product

• 96303-88-7 (-)-10-dicyclohexylsulfamoyl-D-isoborneol 
• 79-10-7 acrylic acid 
• 96303-87-6 N,N-dicyclohexylcamphor-10-sulfonamide 
• 814-68-6 acryloyl chloride 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 21286-54-4 (+)-(1S)-Campher-10-sulfonsaeure-chlorid 

Downstream Products

• 135481-27-5 (1R,5S,6S)-3-Benzyl-8-methyl-2,4-dioxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 114687-47-7 2-(Pyridin-2-ylsulfanyl)-pentanoic acid (1S,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 95-12-5 (-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol 
• 67505-46-8 (-)-exo-Bicyclo<2.2.1>hept-5-en-2-ylmethanol 
• 67671-06-1 (2R)-endo-5-norbornene-2-methanol 
• 67671-05-0 exo-bicyclo<2.2.1>hept-5-en-2-methanol 
• 96303-90-1 (1S,2R,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96303-90-1 (1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96303-90-1 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96303-90-1 (1R,2S,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 379685-55-9 10-N,N-dicyclohexylosulfamoyl-(2R)-isobornyl glyoxylate 
• 496068-17-8 [(1R)-10-(N,N-dicyclohexylsulfamoyl)isobornyl] 2-azidoacrylate 
• 496068-18-9 [(1R)-10-(N,N-dicyclohexylsulfamoyl)isobornyl]-2H-azirine 
• 496068-16-7 2,3-Dibromo-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant articles and documents

Application in asymmetric Morita-Baylis-Hillman reactions

N-Substituted 2-exo-hydroxybornyl-10-sulfonamides, prepared as potential chiral auxiliaries for use in asymmetric Morita-Baylis-Hillman (MBH) reactions, have been treated with acryloyl chloride to afford the corresponding 2-exo-Acrylate esters as MBH subs

The asymmetric hetero-Diels-Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl-(2R)-isobornyl glyoxylate

The recent development of very effective chiral auxiliaries has led to the design of 10-N,N-dicyclohexylsulphamoyl-(R)-isoborneol, which is similar to Oppolzer's (2R)-bornane-10,2-sultam but less effective on account of a less rigid structure. 10-N,N-Dicyclohexylsulphamoyl-(R)-isobornyl glyoxylate was examined in Diels-Alder and organometallic addition reactions. The results obtained were compared with those achieved by application of N-glyoxyloyl-(2R)-bornane-10,2-sultam.

Acyclic stereoselection in the tertiary amine-catalysed addition of activated vinyl systems (Baylis-Hillman reaction) to protected chiral α-hydroxy and α-amino aldehydes

The non chelation-controlled aldol-type addition of the ambident vinyl α anions derived from acrylic esters and methyl vinyl ketone to a series of protected chiral α-hydroxy and α-amino aldehydes has been investigated in order to assess some of the factors which contribute to the control of the diastereofacial selectivity.Whlist the α-methylene-β,γ-disubstituted carbonyl products showed a general preference for selectivity, some examples of syn predominance were made possible via a 'substituent tuning'approach.The observed diastereomer ratios have been interpreted in terms of the Felkin model and the Anh-Eisenstein proposals for 1,2-asymmetric induction.Simple steric effects appear to be as important as ?-orbital energies in the designation of the large 'anti group' for the application of these transition-state interpretations.Attempts to improve the overall induction via double diastereoselection approach, which combines the 1,5-induction of chiral acrylates with the 1,2-induction already present, were largely inconclusive.Methods for the routine NMR assignment of the relevant stereo-substructures have been assessed and the use of novel complementary technique is described.

Chiral acrylates as substrates in Baylis-Hillman reaction

DABCO induces diastereoselective (7-70%) coupling of chiral acrylates (1-3) with aldehydes to produce the corresponding 2-(1-hydroxyalkyl)acrylates.

ASYMMETRIC DIELS-ALDER REACTIONS: FACILE PREPARATION AND STRUCTURE OF SULFONAMIDO-ISOBORNYL ACRYLATES

The crystalline chiral auxiliaries 2, 3 and 4 were prepared from champhor-10-sulfonyl chlorides in 2 steps.Their readily accessible acrylates underwent efficient asymmetric Diels-Alder additions to cyclopentadiene, the topicity of wich agrees with X-ray evidence.