2161-40-2

Basic information

• Product Name: alpha-Methoxytropone
• Synonyms: alpha-Methoxytropone;2-methoxytropolone;2-C-Methoxytropone;Tropolone methyl ether;α-Tropolone methyl ether;2-Methoxycyclohepta-2,4,6-trien-1-one;2-methoxycyclohepta-2,4,6-trienone
• CAS NO: 2161-40-2
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• Mol File: 2161-40-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 130.0 to 134.0 °C
• Boiling Point: 175°C/0.5mmHg(lit.)
• Flash Point: 141.4°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.00255mmHg at 25°C
• Refractive Index: 1.524
• Solubility: soluble in Methanol
• CAS DataBase Reference: alpha-Methoxytropone(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Methoxytropone(2161-40-2)
• EPA Substance Registry System: alpha-Methoxytropone(2161-40-2)

Safety Data

• RTECS: GU4606000
• Hazardous Substances Data: 2161-40-2(Hazardous Substances Data)

Usage

General Description

Alpha-methoxytropone, also known as 3-Methoxy-6-phenyl-5,6,7,8-tetrahydro-4H-benzo[d]azepin-7-ol, is a chemical compound that belongs to the class of tropanes. It is structurally similar to the natural tropane alkaloid, cocaine, and has been identified as a potential drug of abuse. Alpha-methoxytropone is known to have stimulant and dopamine reuptake inhibitory effects, making it a psychoactive substance. Its use has been associated with various adverse effects, including anxiety, agitation, and potential addiction. As a result, it is often regulated as a controlled substance in some jurisdictions. Research on alpha-methoxytropone is ongoing to further understand its pharmacological properties and the potential risks associated with its use.

InChI:InChI=1/C8H8O2/c1-10-8-6-4-2-3-5-7(8)9/h2-6H,1H3

Upstream product

• 125102-15-0 2-methoxy-5-<<(trifluoromethyl)sulfonyl>oxy>tropone 
• 533-75-5 2-hydroxy-2,4,6-cycloheptatrien-1-one 
• 75-05-8 acetonitrile 
• 33739-60-5 3-carboxytropolone 
• 125102-14-9 Trifluoro-methanesulfonic acid 7-oxo-4-trifluoromethanesulfonyloxy-cyclohepta-1,3,5-trienyl ester 
• 15852-34-3 2,5-dihydroxycyclohepta-2,4,6-trien-1-one 
• 74-83-9 methyl bromide 
• 67-56-1 methanol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 72012-54-5 4-methoxy-6,7-dioxabicyclo<3.2.2>nona-2,8-diene 
• 115319-04-5 endo-2-Methoxy-8-oxabicyclo<3.2.1>oct-6-en-3-on 
• 1714-38-1 7-methoxy-1,3,5-cycloheptatriene 
• 539-80-0 Tropone 

Downstream Products

• 100621-68-9 2-o-tolyl-cycloheptatrienone 
• 3480-08-8 2-aminocycloheptimidazole 
• 93-58-3 benzoic acid methyl ester 
• 14562-09-5 2-phenylcyclohepta-2,4,6-triene-1-one 
• 4481-35-0 cyclohepta[b]furan-2(2H)-one 
• 363-67-7 3,5,7-tribromotropolone 
• 76-84-6 triphenylmethyl alcohol 
• 519-73-3 triphenylmethane 
• 99417-38-6 2-<<β-(3,4-dimethoxyphenyl)ethyl>amino>-2,4,6-cycloheptatrien-1-one 
• 50603-71-9 3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one 
• 225112-61-8 2-(triphenylphosphoranylideneamino)tropone 
• 3786-66-1 2-amino-1,3-dicyanoazulene 
• 14628-90-1 2-methoxy-5-nitro-cycloheptatrien-1-one 
• 548475-54-3 7,9-dimethyl-1H-cyclohepta[b]pyrimido[5,4-d]furan-8(7H),10(9H)-dione 

Relevant articles and documents

THE EFFECT ON THE BASE STRENGTHS OF TROPONE AND 2-ALKOXYTROPONES OF ?-COMPLEXATION WITH A Cr(CO)3 GROUP

?-Complexation of tropone and its 2-methoxy and 2-ethoxy derivatives with a Cr(CO)3 group causes an increase in the ketonic base strength by 1.7 +/- 0.3 pK units.

Electrochemical methoxylation of 1,2,3-trisubstituted azulenes

1,2,3-Trisubstituted azulene analogs 6a and 6b easily underwent methoxylation in position 4 or 6 of an azulene ring via an electrochemical oxidation. It is a simple, convenient and selective method for introducing a methoxy group into a 7-membered ring of azulene analogs when compared with traditional chemical methods. It could be useful in preparing 2,4- and 2,6-azuloquinone analogs.

AMBIPHILIC REACTIVITY OF 1,1-DIMETHOXYACETONE

Trialkylsilyloxyallyl cations 2 with a ?-donating methoxy substituent at the allylic termini are generated from nonhalogenated substrates via treatment of 5b-e with Lewis acids. 2 undergoes stereo- and regioselective cycloaddition with furans yielding 2-methoxy-8-oxabicyclooct-6-en-3-ones.Cycloadduct 7 is converted to 2-methoxytropone 14 and thus represents an efficient entry into tropolonoid systems.

Protonation behaviour of 2-phenyl-1,3-diazaazulene derivatives

Three 2-phenyl-1,3-diazaazulene derivatives were synthesized and their protonation behaviours were investigated systematically via UV–vis absorption titration and 1H NMR titration, as well as theoretical calculations. One of them exhibited a monoprotonation process while the others displayed prominent halochromic diprotonation responses. Interestingly, upon protonation of 2-phenyl-1,3-diazaazulene derivatives, the coplanarity and conjugation of the 16-π-conjugated backbones were well kept, while the electronic structures were controllably adjusted. The response mechanism of 1,3-diazaazulene derivatives towards acid is through the attachment of acid proton to the nitrogen atom in the diazaazulene ring, resulting in the change of the hybridization of protonated-N from sp2 to sp3, which differed from that of the well-known azulene (analogue of 1,3-diazaazulene, protonation at carbon atom). This work would provide a new insight into the protonation research of the organic functional molecules.

Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A

Hippolachnin A (1) is an antifungal polyketide that bristles with ethyl groups mounted onto a caged heterotricyclic core. It has shown potent activity against Cryptococcus neoformans, a yeast that can affect immunocompromised patients as an opportunistic pathogen. Herein we describe a concise, diversifiable, and scalable synthesis of (±)-hippolachnin A (1). It features a powerful photochemical opening step, a diastereoselective addition of an ethyl cuprate and an unusual strategy to install two additional ethyl groups that makes use of a thiocarbonyl ylide generated in situ.