1415637-17-0

Basic information

• Product Name: N-methoxy-4-nitro-N-((R)-1-((1R,2S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-yl)ethyl)benzenesulfonamide
• CAS NO: 1415637-17-0
• Molecular Weight: 394.492
• Mol File: 1415637-17-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-methoxy-4-nitro-N-((R)-1-((1R,2S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-yl)ethyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methoxy-4-nitro-N-((R)-1-((1R,2S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-yl)ethyl)benzenesulfonamide(1415637-17-0)
• EPA Substance Registry System: N-methoxy-4-nitro-N-((R)-1-((1R,2S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-yl)ethyl)benzenesulfonamide(1415637-17-0)

Safety Data

• Hazardous Substances Data: 1415637-17-0(Hazardous Substances Data)

Upstream product

• 1415636-95-1 N-methoxy-N-((S)-1-((1R,2S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-yl)ethyl)acetamide 
• 122-04-3 4-nitro-benzoyl chloride 
• 3608-11-5 4-α-acetyl-2-carene 

Relevant articles and documents

Tandem nucleophilic addition/oxy-2-azonia-cope rearrangement for the formation of homoallylic amides and lactams: Total synthesis and structural verification of motuporamine G

In the presence of a Lewis acid, β,γ-unsaturated ketones and oximes or imines undergo nucleophilic addition to produce zwitterion intermediates, and subsequent oxy-2-azonia-Cope rearrangements give homoallylic amides. In the case of 2-vinylcycloalkanones, the process results in ring enlargement, providing a novel route to 9- to 16-membered lactams. The preparative significance of this protocol was evidenced by a short synthesis of macrocyclic alkaloid motuporamine G. The stereochemistry-defining step of this oxy-azonia-Cope rearrangement was further studied computationally. Despite a high-energy preequilibrium in the formation of zwitterionic intermediates, the [3,3]-sigmatropic step is the rate- and product-determining step. Chairlike transition states are generally preferred over boatlike ones.