40154-02-7

Upstream product

• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 141-78-6 ethyl acetate 
• 92508-62-8 ethyl 2-(1-hydroxy-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate 
• 1730-48-9 6-methoxy-1,2,3,4-tetrahydronaphthalene 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 87901-81-3 ethyl 6-methoxy-1-naphthaleneacetic acid 
• 99417-01-3 3-<2-(6-methoxy-1-naphthyl)ethyl>-2-cyclohexeneone 
• 99417-11-5 Benzenesulfonic acid 2-(6-methoxy-naphthalen-1-yl)-ethyl ester 

Relevant academic research and scientific papers

Synthesis of novel molecular probes inspired by harringtonolide

A novel harringtonolide-inspired scaffold containing a cycloheptatriene ring and two fused cyclopentane rings has been synthesised from simple starting materials. The scaffold, containing a similar substitution pattern and relative stereochemistry to the

Construction of functionalized indans by thallium(III) promoted ring contraction of 3-alkenols

An efficient four step protocol for the construction of functionalized indans was developed. 1-Tetralones were transformed into unsaturated esters by Reformatsky reaction with bromo-esters (ethyl 2-bromopropionate, ethyl bromoacetate or ethyl 2-bromobutyrate), followed by dehydration of the β-hydroxy-ester formed. Reduction of the ester moiety led to homoallylic alcohols bearing an endocyclic double bond. The oxidative rearrangement of these 3-alkenols was performed by thallium trinitrate (TTN) in a 2:1 mixture of AcOH/H2O, leading to the ring contraction products in moderate to very good yield. Fourteen examples of this sequence were studied. The oxidation of 3-alkenols prepared from 2-tetralones with TTN was also investigated. With these substrates the ring contraction reaction was not observed.

Methoxybenzopyrene 4,5-Oxides Labeled with Carbon-13: Electronic Effects in the NIH Shift

The synthesis of 9-methoxy-4,5-dihydrobenzopyrene-4-13C4,5-oxide and -5-13C4,5-oxide and of 8-methoxy-4,5-dihydrobenzopyrene-4-13C4,5-oxide is reported.The compounds were synthesized in yields of 15percent each from unlabeled precursors. 13C NMR analysis of the conversion of the 4,5-oxides to 4-phenols and 5-phenols (NIH shift) revealed a very strong electronic effect of a 9-methoxy substituent, which gave only the 4-phenol, and a significant but weaker effect of an 8-methoxy substituent, which gave both phenols with the 5-phenol predominating.