195608-41-4

Upstream product

• 195608-40-3 (Z)-1-tert-butyldimethylsilyloxy-9-(4-methylphenylsulfonamido)non-4-ene-2,6-diyne 
• 195608-39-0 (Z)-1-(4-methylphenylsulfonamido)-6-chlorohex-5-en-3-yne 
• 195608-37-8 (Z)-1-azido-6-chlorohex-5-en-3-yne 
• 292152-94-4 (Z)-6-chlorohex-5-en-3-ynyl methanesulfonate 
• 195608-38-9 (Z)-1-amino-6-chlorohex-5-en-3-yne 
• 114534-21-3 (Z)-6-chlorohex-5-en-3-yn-1-ol 
• 124-63-0 methanesulfonyl chloride 
• 292152-95-5 9-(4-methylphenylsulfonamido)non-4-ene-2,6-di-diyne-1-ol 

Downstream Products

• 20335-69-7 2-tosyl-1,2,3,4-tetrahydroisoquinoline 
• 195608-42-5 1-(4-methylphenylsulfonyl)-1-azacyclodec-5-ene-3,7-diyne 

Relevant academic research and scientific papers

The synthesis and reactivity of a novel 10-membered azaenediyne

Monocyclic azaenediyne 6 have been synthesized and has a half life of -36 h in CDCl3 at 30°C.

Nitrogen substituted cyclic enediynes: Synthesis, thermal reactivity and coniplexation with metal ions

A number of N-substituted cyclic enediynes (azaenediynes) have been synthesized via Pd(0)-catalysed ene-yne coupling followed by N-alkylation. The simplest of them, a 10-membered monocyclic enediyrie 1, underwent Bergman cyclization (BC) at 23°C with a half-life of 72 h. The kinetics of BC slowed down considerably by fusing a benzene ring onto the enediyne. Several novel bis(azaenediyne)s and bis(diazaenediyne)s 3-6 have been synthesized. Their onset temperatures for BC were lowered under metal ion complexation conditions. The Royal Society of Chemistry 2000.

Studies on Bergman cyclization, the chemistry at the heart of enediynes

The kinetics of Bergman cyclization (BC) which is dependent upon a number of steric and stereoelectronic parameters, have been studied in various nitrogen-substituted cyclic enediynes. The simplest of these, a 10-membered enediyne 33 cyclized spontaneously (t1/2 = 72 h at 23°) and caused significant cleavage of supercoiled double stranded DNA at micromolar level. The degree of pyramidalization of the ring nitrogen in these enediynes has an inverse effect on the rate of cyclization. Replacement of the ene part with an aromatic ring led to a considerable elevation of activation energy for BC.