539-80-0

Basic information

• Product Name: TROPONE
• Synonyms: TROPONE;2,4,6-Cyclo-heptatriene-1-one;2,4,6-Cycloheptatriene-1-one;cyclohepta-2,4,6-trienone;Cycloheptatrienone;Tropon;2,4,6-CYCLOHEPTATRIEN-1-ONE;2,4,6-CYCLOHEPTATRIENONE
• CAS NO: 539-80-0
• Molecular Formula: C₇H₆O
• Molecular Weight: 106.12
• EINECS: 208-725-6
• Mol File: 539-80-0.mol
• Article Data: 43

Chemical Properties

• Melting Point: -7°C
• Boiling Point: 113 °C15 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: very deep brown/
• Density: 1.091 g/mL at 20 °C
• Vapor Pressure: 0.124mmHg at 25°C
• Refractive Index: n20/D 1.615(lit.)
• Storage Temp.: −20°C
• BRN: 1902335
• CAS DataBase Reference: TROPONE(CAS DataBase Reference)
• NIST Chemistry Reference: TROPONE(539-80-0)
• EPA Substance Registry System: TROPONE(539-80-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 539-80-0(Hazardous Substances Data)

Usage

Chemical Description

Tropone is a cyclic ketone with a seven-membered ring.

Chemical Description

Tropone is obtained by heating allyl tropyl ether at 65" in aqueous THF.

Description

TROPONE is a chemical compound that is known for its unique properties and versatile applications in various fields. It is a bicyclic compound with a structure that allows it to participate in a range of chemical reactions, making it a valuable component in the synthesis of various complex molecules.

Uses

Used in Pharmaceutical Industry:
TROPONE is used as a key intermediate for the synthesis of complex organic molecules, particularly in the development of new drugs and pharmaceutical compounds. Its ability to undergo various chemical reactions makes it a valuable asset in the creation of novel therapeutic agents.
Used in Chemical Synthesis:
TROPONE is used as a building block for the synthesis of various complex organic compounds, such as bicyclic δ-lactones and 6,7-benzobicyclo[3.2.2]nona-3,6,8-trien-2-one. Its unique structure and reactivity enable the formation of these compounds through different pathways, such as heterocyclic carbine-catalyzed [8+3] annulation and thermal addition to bezyne.
Used in Research and Development:
TROPONE is used as a research compound in the study of metal-catalyzed [6+3] cycloaddition reactions with azomethine ylides. This application helps scientists understand the underlying mechanisms and develop new strategies for the synthesis of complex molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 5442, 1956 DOI: 10.1021/ja01601a077The Journal of Organic Chemistry, 29, p. 960, 1964Organic Syntheses, Coll. Vol. 9, p. 396, 1998

InChI:InChI=1/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H

Upstream product

• 29798-82-1 2,4,7-tribromotropone 
• 1714-38-1 7-methoxy-1,3,5-cycloheptatriene 
• 1901-34-4 cyclohepta-2,4-dienone 
• 698-18-0 2-hydrazinotropone 
• 30456-90-7 thiotropone 
• 40458-77-3 8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 1714-40-5 3-methoxy-1,3,5-cycloheptatriene 
• 18207-24-4 7,7-dimethoxy-1,3,5-cycloheptatriene 
• 531-45-3 heptafulvalene 
• 16273-47-5 ditropylether 
• 27081-10-3 tropylium tetrafluoroborate 
• 81236-28-4 9,9-Dioxo-9λ⁶-thia-bicyclo[3.3.1]nona-3,7-diene-2,6-dione 
• 122334-44-5 9-<1-(2,4,6-cycloheptatrienyl)>-9-xanthydrol 
• 75359-40-9 ditropenyliumyl ether bis(trifluoromethanesulfonate) 

Downstream Products

• 36161-80-5 2-phenyl-(3at,8at)-3a,4,8,8a-tetrahydro-4r,8c-etheno-cyclohepta[c]pyrrole-1,3,5-trione 
• 40638-56-0 (2Z,4Z,6Z)-2-(4-Nitro-phenyl)-cycloocta-2,4,6-trienone 
• 40638-55-9 2.3-Di-p-nitrophenyl-propiophenon 
• 55609-46-6 3-phenyl-4H-cycloheptaisoxazol-4-one 
• 55609-40-0 3-phenyl-5,6-dihydro-cyclohepta[d]isoxazol-4-one 
• 55652-68-1 9-phenyl-7-oxa-8-aza-bicyclo[4.3.1]deca-2,4,8-trien-10-one 
• 55609-42-2 3,7-diphenyl-(6ar,9ac)-5,6,6a,9a-tetrahydro-cyclohepta[1,2-d;4,3-d']diisoxazol-4-one 
• 55609-44-4 3,9-diphenyl-(6ar,9ac)-5,6,6a,9a-tetrahydro-cyclohepta[1,2-d;3,4-d']diisoxazol-4-one 
• 55609-39-7 3,5-diphenyl-(3ar,4at,7at,9ac)-3a,4a,7a,9a-tetrahydro-cyclohepta[2,1-d;4,5-d']diisoxazol-4-one 
• 55609-47-7 3-(2,4,6-trimethyl-phenyl)-cyclohepta[d]isoxazol-4-one 
• 55609-38-6 9-(2,4,6-trimethyl-phenyl)-7-oxa-8-aza-bicyclo[4.3.1]deca-2,4,8-trien-10-one 
• 55609-43-3 3,7-bis-(2,4,6-trimethyl-phenyl)-(6ar,9ac)-5,6,6a,9a-tetrahydro-cyclohepta[1,2-d;4,3-d']diisoxazol-4-one 
• 55609-45-5 3,9-bis-(2,4,6-trimethyl-phenyl)-(6ar,9ac)-5,6,6a,9a-tetrahydro-cyclohepta[1,2-d;3,4-d']diisoxazol-4-one 
• 725-73-5 1,2,3-Trichlor-6-<4-methoxyphenyl>-fulven 

Relevant articles and documents

Tropone

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Organocatalytic stereoselective [8+2] and [6+4] cycloadditions

Cycloadditions that involve more than six I € electrons are termed higher-order cycloadditions and are an excellent tool for solving complex synthetic challenges, as they provide direct access to polycyclic scaffolds that contain medium-sized rings. They have interesting synthetic potential for the discovery of new bioactive molecules and in natural product synthesis. It is peculiar that stereocontrolled [8+2] and [6+4] cycloadditions have been largely neglected for the past 50 years. Here we demonstrate a cross-dienamine activation of 2-cyclopentenone and the unprecedented endocyclic linear-dienamine activation of 2-cyclohexenones and 2-cycloheptenones. These dienamine intermediates undergo aminocatalytic stereoselective [8+2], [6+4] and formal [4+2] cycloadditions with various heptafulvenes. The periselectivities of the cycloadditions are controlled based on the ring size of the 2-cycloalkenones and the substitution patterns of the heptafulvenes. The chiral products obtained undergo various chemical and photochemical single-step transformations that give access to other classes of all-carbon polycyclic scaffolds.

DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene

An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.

Dialkylated Dihydroazulene and Vinylheptafulvene Derivatives – Synthesis and Switching Properties

Functionalization of molecular photoswitches at specific positions offers a way of tuning their switching properties. The work presented here describes the development of a new protocol towards the synthesis and functionalization of the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The key step is a facile condensation reaction using a functionalized tropone derivative, and the new synthetic method was employed in the regioselective preparation of a novel dimethyl-substituted DHA photoswitch. This compound presents the first accessible derivative with alkyl groups on the seven-membered ring of the system ― at positions C5 and C7. From experimental and theoretical kinetics studies on the thermal VHF-to-DHA electrocyclic reaction, the influence of the electron-donating methyl groups was elucidated. In addition, we subjected a small selection of 4,8a-dialkylated compounds to a computational study to elucidate how steric interactions can alter the relative DHA–VHF stabilities. The synthetic methodology offers access to novel DHA scaffolds and substitution patterns, which in turn can lead to systems that can help to address broader questions concerning the potential applicability of the DHA/VHF system in the context of solar-thermal energy-storage systems or other photochromic applications.