1415637-10-3

Basic information

• Product Name: methoxy-14-methyl-16-(4-nitrophenyl)azacyclohexadec-13-en-2-one
• CAS NO: 1415637-10-3
• Molecular Weight: 402.534
• Mol File: 1415637-10-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methoxy-14-methyl-16-(4-nitrophenyl)azacyclohexadec-13-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: methoxy-14-methyl-16-(4-nitrophenyl)azacyclohexadec-13-en-2-one(1415637-10-3)
• EPA Substance Registry System: methoxy-14-methyl-16-(4-nitrophenyl)azacyclohexadec-13-en-2-one(1415637-10-3)

Safety Data

• Hazardous Substances Data: 1415637-10-3(Hazardous Substances Data)

Upstream product

• 33499-32-0 (E/Z)-4-nitrobenzaldehyde O-methyl oxime 

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.