3674-65-5

Usage

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

Upstream product

• 860550-12-5 4a-chloromethyl-2,3-dimethyl-1,4,4a,9,10,10a-hexahydro-phenanthrene 
• 64-19-7 acetic acid 
• 1008760-88-0 2,2'-(4,5-dimethyl-1,2-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 153140-75-1 1-bromo-2-[(Z)-2-bromoethenyl]benzene 
• 63609-36-9 3,4-Dimethylphenylacetat 
• 63609-31-4 1-(2-Methoxy-4,5-dimethyl-phenyl)-2-phenyl-ethanol 
• 54468-76-7 2-methoxy-4,5-dimethyl-deoxybenzoin 
• 18439-99-1 2-phenylacetyl-4,5-dimethylphenol 
• 95-65-8 3,4-Dimethylphenol 
• 95-47-6 o-xylene 
• 63609-32-5 2-Methoxy-4,5-Dimethylstilben 
• 101790-01-6 2,3-Dimethyl-1,4,9,10,11,12-hexahydrophenanthren-dicarbonsaeure-(11,12)-anhydrid 
• 861004-99-1 4-Hydroxy-2.3-dimethyl-1.2.3.4-tetrahydro-phenanthren 
• 857627-94-2 2,3-dimethyl-2,3-dihydro-1H-phenanthren-4-one 

Downstream Products

• 89-05-4 1,2,4,5-benzenetetracarboxylic acid 

Relevant academic research and scientific papers

Tandem acylation-cycloalkylation: A novel synthesis of phenanthrenes

Cyclohexene-1-acetic acid (1) undergoes reaction with various aromatic substrates 2a-k in the presence of polyphosphoric acid (PPA) to give 1,2,3,4,4a,10a-hexahydrophenanthren-9(10H)-ones 3a-k by tandem acylation-cycloalkylation, which on dehydrogenation with Pd-C afforded the corresponding phenanthrenes 4a-k in high yields.

Palladium-catalyzed annulation of 1,2-diborylalkenes and -arenes with 1-bromo-2-[(Z)-2-bromoethenyl]arenes: A modular approach to multisubstituted naphthalenes and fused phenanthrenes

(Z)-1,2-Diaryl-1,2-bis(pinacolatoboryl)ethenes underwent double-cross-coupling reactions with 1-bromo-2-[(Z)-2-bromoethenyl]arenes in the presence of [Pd(PPh3)4] as a catalyst and 3 M aqueous Cs2CO3 as a base in THF at 80 °C. The double-coupling reaction gave multisubstituted naphthalenes in good to high yields. Annulation of 1,2-bis(pinacolatoboryl)arenes with bromo(bromoethenyl)arenes in the presence of a catalyst system that consisted of [Pd2(dba)3] (dba=dibenzylideneacetone) and 2-dicyclohexylphosphino-2′,6′- dimethoxybiphenyl (SPhos) under the same conditions produced fused phenanthrenes in good to high yields. The first annulation coupling occurred regiospecifically at the bromoethenyl moiety. This procedure is applicable to the facile synthesis of polysubstituted anthracenes, benzothiophenes, and dibenzoanthracenes through a double annulation pathway by using the corresponding dibromobis[(Z)-2-bromoethenyl]benzenes as diboryl coupling partners. Copyright

A short three-component synthesis of tricyclic compounds

A facile reaction sequence, consisting of a palladium-catalyzed Sonogashira coupling, a cobalt-catalyzed Diels - Alder reaction and a subsequent cyclization initiated by a bromine-lithium exchange reaction, allows a three-component synthesis of tricyclic