20291-72-9

Usage

Uses

1,2-Dimethylphenanthrene is a biodegrdation product of alkylphenanthrenes.

InChI:InChI=1/C16H14/c1-11-7-9-16-14(12(11)2)10-8-13-5-3-4-6-15(13)16/h3-10H,1-2H3

Upstream product

• 855615-03-1 3,4-dimethyl-phenanthrene-1,2-dicarboxylic acid-anhydride 
• 352026-71-2 2-hydroxy-7,8-dimethylphenanthrene 
• 873966-98-4 2-ethyl-1,2-dimethyl-1,2,3,4-tetrahydro-[1]phenanthrol 
• 97277-92-4 1,2,3,4-tetrahydro-1,1-dimethylphenanthrene 
• 97277-93-5 2,2-dimethyl-1,2,3,4-tetrahydrophenanthrene 
• 71-43-2 benzene 
• 97277-98-0 1,2-dimethyl-3,4-dihydrophenanthrene 
• 53863-91-5 α,α-(2,3-Dimethylcyclopentan)-γ-phenylbuttersaeure 
• 30436-48-7 3,7'-dimethyl-3',4'-dihydro-spiro[cyclopentane-1,2'-naphthalen]-1'-one 
• 31599-60-7 1-iodo-2,3-dimethylbenzene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 7154-66-7 2-bromobenzoic acid chloride 
• 1241978-46-0 2-(2-bromonaphthalen-1-yl)-4,5-dimethyl-3,6-dihydro-2H-pyran 
• 30436-46-5 α.α-(2.3-Dimethylcyclopentan)-β-benzoylpropionsaeure 

Relevant academic research and scientific papers

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromoben-zoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.

Synthesis of phenanthrene and alkyl phenanthrenes by palladium(0)-catalyzed pericyclic reactions

Palladium-catalyzed pericyclic reactions have been developed for the synthesis of phenanthrenes. This method is also useful for the synthesis of monoalkyl and dialkyl phenanthrene derivatives. Georg Thieme Verlag Stuttgart.

Synthesis of alkylphenanthrenes from naphthylalkylidenemalonodinitriles. A route to 1-methyl-, 2-methyl-, and 1,2-dimethylphenanthrene

The study has been carried out to evaluate the feasibility of synthesis of 1-methyl-, 2-methyl-, 1,2-dimethyl-, and 1-ethyl-2-methylphenanthrene through the annulation of the naphthalene system with the exploitation of the dicyanovinyl moiety of 2-naphthylalkylidenemalonodinitriles as an active electrophile in cold solutions of concentrated sulfuric acid. 2-(2-Naphthyl)propanal (3), 1-(2-naphthyl)propan-2-one (9), 3-(2-naphthyl)butan-2-one (14), and 3-(2-naphthyl)pentan-2-one (19) had been condensed with malonodinitrile to afford 2-naphthylalkylidenemalonodinitriles which were then cyclised to give 4-amino-1-methylphenanthrene-3-carbonitrile (5), 4-amino-2-methylphenanthrene-3-carbonitrile (11), 4-amino-1,2-dimethylphenanthrene-3-carbonitrile (16), and 4-amino-1-ethyl-2-metylphenanthrene-3-carbonitrile (21). The nitrile function has been removed from the aminonitriles, with the exception of 21, through hydrolysis and decarboxylation in alkaline ethanolic solutions under elevated pressure (～3 MPa) and temperature 220-230°C to give the respective 4-amino-methylphenanthrenes. Diazotisation of the phenanthreneamines and the reaction with hypophosphorus acid has lead to the methylphenanthrenes in moderate yields (50-52%).