13656-81-0

Basic information

• Product Name: 4-Isopropyltropone
• Synonyms: 4-Isopropyl-2,4,6-cycloheptatrien-1-one;4-Isopropyltropone;Nezukone
• CAS NO: 13656-81-0
• Molecular Formula: C10H12O
• Molecular Weight: 148.2
• Mol File: 13656-81-0.mol

Chemical Properties

• Boiling Point: 127-128 °C(Press: 5 Torr)
• Appearance: /
• Density: 1.0170 g/cm3(Temp: 16 °C)
• CAS DataBase Reference: 4-Isopropyltropone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropyltropone(13656-81-0)
• EPA Substance Registry System: 4-Isopropyltropone(13656-81-0)

Safety Data

• Hazardous Substances Data: 13656-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Isopropyltropone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-Isopropyltropone serves as a valuable building block for the synthesis of more complex molecules. Its reactivity and structural features make it a useful starting material for creating a wide range of chemical products, including fragrances, dyes, and other specialty chemicals.
Used in Flavor and Fragrance Industry:
Due to its distinct aroma and volatility, 4-Isopropyltropone is used as a component in the creation of various fragrances and flavors. Its unique scent profile can be utilized to enhance or modify the overall aroma of perfumes, colognes, and other scented products.
Used in Research and Development:
4-Isopropyltropone is also employed in research and development settings, where it can be used to study the properties and behavior of similar compounds. Its unique structure and reactivity make it an interesting subject for scientific investigation, potentially leading to new discoveries and innovations in the field of chemistry.

Upstream product

• 110087-11-1 6-isopropyltricyclo<4.1.0.0^2,7>heptan-3-one 
• 917-54-4 methyllithium 
• 115957-56-7 methyl 4-oxo-1,6-cycloheptadiene-1-carboxylate 
• 126893-33-2 3-Isopropyl-7,7-dimethoxy-cyclohepta-1,3,5-triene 
• 73516-42-4 1-isopropylcyclohepten-5-one 
• 56410-49-2 4-Isopropyl-cyclohepta-2,6-dienone 
• 499-44-5 hinokitiol 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 69141-44-2 2-chloro-4-isopropyltropone 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 126893-59-2 4-Isopropyl-1-methoxy-cyclohepta-1,3,5-triene 
• 126893-52-5 7-Isopropyl-3-methoxy-cyclohepta-1,3,5-triene 
• 1714-38-1 7-methoxy-1,3,5-cycloheptatriene 
• 1728-32-1 1-methoxycyclohepta-1,3,5-triene 

Relevant articles and documents

A Novel Synthesis of Nezukone via the Rearrangement of a Bicyclic Isomer: Evidence for the Intermediacy of Heptafulvenes

The bicyclic methylenecyclopropane (2) is converted into nezukone (1) in 61percent yield; evidence is presented which suggests heptafulvenes are involved in this conversion.

HINOKITIOL ANALOGUES, METHODS OF PREPARING AND PHARMACEUTICAL COMPOSITIONS THEREOF

Disclosed are analogues of hinokitiol, methods for preparing them, and pharmaceutical compositions thereof. Also disclosed are methods for their use in treating iron-related diseases.

Homocoupling of halotropones promoted by bis(1,5-cyclooctadiene) nickel in the presence of tris(1-pyrazolyl)methane: an easy route to [Bi-1,3,5- cycloheptatrien-1-yl]-7,7'-diones

An efficient homocoupling of 2-halotropones, to afford 2,2'-bitropones, occurs in toluene at rt in the presence of stoichiometric amounts of [Ni(cod)2] and tris(1-pyrazolyl)methane ligand, in a 1:1 molar ratio. This methodology was extended to aryl halides. Copyright Taylor & Francis Group, LLC.

Cycloaddition of acyclic conjugated dienes with a tetrachloro- substituted oxyallyl intermediate generated from pentachloroacetone

Pentachloroacetone (1) reacts with several conjugated dienes in the presence of sodium trifluoroethoxide/trifluoroethanol to form cycloadducts of a tetrachlorooxyallyl intermediate 6, mainly in the [4+3] mode. Representative [4+3] cycloadducts, i.e. α,α,α',α'- tetrachlorocycloheptenones 9, have been dehalogenated and dehydrohalogenated, furnishing α,α'-dichlorotropones 15 in high yields.

Synthesis of the Troponoid Natural Product Nezukone via Sequential Rearrangement of Two Isomeric Precursors

Nezukone (1) has been synthesized in seven steps from the readily available Δ3-trinorcarene (4).Key features of the sequence used include formation of the bicyclic isomer (2) of compound (1).Base-promoted isomerization of compound (2) followed

Anodic oxidation of cycloheptatriene systems and its application to the synthesis of non-benzenoid aromatic compounds

Anodic oxidation of cycloheptatrienes has been found to be one of the most powerful key tools for the preparation of a variety of non-benzenoid aromatic compounds such as tropylium salts, tropones, tropolones, 2H-cyclohepta[b]furan-2-ones, and azulenes.

Versatile Synthesis of Tropones by Reaction of Rhodium(II)-Stabilized Vinylcarbenoids with 1-Methoxy-1-buta-1,3-diene

Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-buta-1,3-diene leads to annulation products by a tandem cyclopropanation/Cope rearrangement sequence.The resulting cycloheptadienes are r

A NOVEL REGIOSELECTIVE SYNTHESIS OF 4-SUBSTITUTED TROPONES

The preparation of 4-alkyl (or aryl) tropones has easily been accomplished by the anodic oxidation of 1-methoxy-4-alkyl (or aryl) cycloheptatrienes which where synthesized by the regioselective addition of alkyl or aryl lithium to 3-position of 7,7-dimethoxycycloheptatriene followed by the thermal 1,5-hydrogen shift of the resulting 3-methoxy-7-alkyl (or aryl) cycloheptatrienes.

204. The Reaction of 1,3-Butadiene with Ethyl Diazopyruvate. Syntheses of Salicylates and of Nezukone

The Rh-catalyzed reaction of 1,3-butadiene with ethyl 3-diazopyruvate leads, inter alia, to a dihydro-oxepinecarboxylate whose oxidation and functional-group manipulation produce salicylates.Wittig reactions on the acylcyclopropane accompanying the dihydrooxepine yields acrylates whose pyrolyses afford cycloheptadienecarboxylates.Oxidation and functional-group transformation produces the natural tropone, nezukone.

A Photochemical route to 4-Alkyltropones including Nezukone

An acetonitrile solution of acetylene and 3-methylcyclopent-2-enone (4) was irradiated with Pyrex-filtered light from a mercury lamp to give 5-methylbicyclohept-6-en-2-one (6) and 6-methyl-tricyclo2,7>heptan-3-one (8).These were easily separated and when heated under reflux in ButOH with SeO2 gave the 4-methyltropone valence-tautomer 5-methylbicyclohept-3,6-dien-2-one (10) and 4-methyltropone (12), respectively, the latter in 20percent overall, unoptimized yield.Similar reactions with 3-isopropylcyclopent-2-enone (5) in the place of (4) led to the natural troponoid 4-isoproyltropone (nezukone) (13).