133157-17-2

Upstream product

• 133157-12-7 (Z)-Methyl 9-tosyloxyoctadec-12-enoate 
• 133157-14-9 (Z)-Methyl 9-azidooctadec-12-enoate 
• 133157-13-8 (Z)-Methyl 9-mesyloxyoctadec-12-enoate 
• 133157-11-6 (Z)-Methyl 9-chlorooctadec-12-enoate 
• 10026-39-8 isoricinoleic acid methyl ester 
• 133157-15-0 methyl 8-(5-hexyl-1-pyrroline-1-yl)octanoate 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

Synthesis and Properties of a Novel 1-Pyrroline Fatty Ester Derivative from Methyl Isoricinoleate

Reaction of methyl isoricinoleate with toluene-p-sulphonyl chloride gave a mixture of (Z)-methyl 9-chlorooctadec-12-enoate 2 and (Z)-methyl 9-tosyloxyoctadec-12-enoate 3 and with methane sulphonyl chloride the corresponding mesyloxy derivative 4.Treatment of compounds 2-4 with NaN3 in N,N-dimethylformamide at 50 deg C gave (Z)-methyl 9-azidooctadec-9-enoate 5, while at 80 deg C methyl 8-(5-hexyl-2-pyrrolin-1-yl)octanoate 6 was obtained.The 1-pyrroline ring was characterized by IR, 1H and 13C NMR spectroscopy, while the ring cleavage products (methyl 9-acetamido-12-oxooctadecanoate 7 and methyl 9-benzamido-12-oxooctadecanoate 8) were characterized by GC-MS.Reduction of the C=N bond in compound 6 with NaBH4 gave a mixture of E- and Z-isomers of the corresponding disubstituted pyrrolidine fatty esters 9a and 9b.