219314-01-9

Basic information

• Product Name: (E)-15-norcaryophyll-4-en-8β-yl tosylate
• CAS NO: 219314-01-9
• Molecular Weight: 362.533
• Mol File: 219314-01-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-15-norcaryophyll-4-en-8β-yl tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-15-norcaryophyll-4-en-8β-yl tosylate(219314-01-9)
• EPA Substance Registry System: (E)-15-norcaryophyll-4-en-8β-yl tosylate(219314-01-9)

Safety Data

• Hazardous Substances Data: 219314-01-9(Hazardous Substances Data)

Upstream product

• 60362-44-9 (1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 10306-22-6 (1R,4R,6R,10S)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0^4,6]dodcan-9-one 
• 1139-30-6 caryophyllene oxide 

Relevant articles and documents

Solvolysis of caryophyllen-8β-yl derivatives: Biomimetic rearrangement- cyclization to 12-nor-8α-presilphiperfolan-9β-ol

The solvolyses of caryophyllen-8β-yl p-nitrobenzoate (14-OpNB) and 15- norcaryophyllen-8β-yl tosylate (15-OTs) were investigated as potential model reactions for the biogenesis of the tricyclic presilphiperfolanol sesquiterpenes. Buffered solvolysis of 14-OpNB in 60% aqueous acetone at 125 °C afforded caryophyllene (3) as major product, accompanied by small amounts of caryophyllen-8β-ol (14-OH) and 5,8-cyclocaryophyllen-4α-ol (16). In contrast, 15-OTs underwent a stereospecific rearrangement-cyclization to 12- nor-8α-presilphiperfolan-9β-ol (17) upon solvolysis in 60% aqueous acetone at 75 °C. The structure and stereochemistry of this trans,cis,trans- tricyclo[6.2.1.05,11]-undecane derivative were established by NMR correlation spectroscopy and X-ray crystallography. Two different mechanisms (paths A and B) for the conversion of 15-OTs to 17 by initial 1,2-migration of either the external or internal cyclobutane ring bonds (C10 and C1) followed by π-σ cyclization onto the trans double bond are discussed.