72335-50-3

Basic information

• Product Name: Cyclohexanecarboxylic acid, 1-(2-propen-1-yl)-
• Synonyms: Cyclohexanecarboxylic acid, 1-(2-propen-1-yl)-;1-(prop-2-en-1-yl)cyclohexane-1-carboxylic acid
• CAS NO: 72335-50-3
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: -0
• Mol File: 72335-50-3.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexanecarboxylic acid, 1-(2-propen-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 1-(2-propen-1-yl)-(72335-50-3)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 1-(2-propen-1-yl)-(72335-50-3)

Safety Data

• Hazardous Substances Data: 72335-50-3(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 115993-77-6 1-(phenylthio)-1-(2-propenyl)cyclohexane 
• 67838-02-2 methyl 1-allylcyclohexane-1-carboxylate 
• 106-95-6 allyl bromide 
• 98-89-5 Cyclohexanecarboxylic acid 
• 37457-08-2 cyclohexane-1,1-diylbis(phenylsulfane) 
• 108-94-1 cyclohexanone 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 107-05-1 3-chloroprop-1-ene 
• 1196662-63-1 allyl 1-bromocyclohexanecarboxylate 
• 29548-87-6 1-bromocyclohexanecarboxylic acid chloride 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 636-82-8 cyclohexene-1-carboxylic acid 

Downstream Products

• 72335-83-2 1-allylcyclohexane-1-carboxylic acid chloride 
• 76403-25-3 1-Allyl-cyclohexanecarbonyl azide 
• 81097-43-0 1-allyl-1-(aminomethyl)cyclohexane 
• 72335-77-4 1-Allyl-cyclohexanecarboxylic acid amide 
• 81097-22-5 N-((1-allylcyclohexyl)methyl)-4-methylbenzenesulfonamide 
• 134786-21-3 N-tosyl-2-azaspiro<4,5>decane-3-methanol 
• 134786-29-1 N-tosyl-α,α-dimethyl-2-azaspiro<4,5>decane-3-methanol 
• 134786-33-7 acide N-tosyl-2-azaspiro<4,5>decane-3-carboxylique 
• 72335-72-9 sodium 1-allyl-1-cyclohexyl-carboxylate 
• 1310538-80-7 2-tosyl-3-(3-(triisopropylsilyl)prop-2-ynyl)-2-azaspiro[4.5]decan-1-one 
• 1310538-68-1 1-allyl-N-tosylcyclohexanecarboxamide 
• 1427450-03-0 3-(fluoromethyl)-2-phenyl-2-azaspiro[4.5]decan-1-one 
• 1427450-17-6 1-allyl-N-phenylcyclohexane-1-carboxamide 
• 67838-03-3 1-(1-(2-propenyl)cyclohexyl)methanol 

Relevant articles and documents

Iodoarene-Catalyzed Oxyamination of Unactivated Alkenes to Synthesize 5-Imino-2-Tetrahydrofuranyl Methanamine Derivatives

Reported here is the room-temperature metal-free iodoarene-catalyzed oxyamination of unactivated alkenes. In this process, the alkenes are difunctionalized by the oxygen atom of the amide group and the nitrogen in an exogenous HNTs2 molecule. This mild and open-air reaction provided an efficient synthesis to N-bistosyl-substituted 5-imino-2-tetrahydrofuranyl methanamine derivatives, which are important motifs in drug development and biological studies. Mechanistic study based on experiments and density functional theory calculations showed that this transformation proceeds via activation of the substrate alkene by an in situ generated cationic iodonium(III) intermediate, which is subsequently attacked by an oxygen atom (instead of nitrogen) of amides to form a five-membered ring intermediate. Finally, this intermediate undergoes an SN2 reaction by NTs2 as the nucleophile to give the oxygen and nitrogen difunctionalized 5-imino-2-tetrahydrofuranyl methanamine product. An asymmetric variant of the present alkene oxyamination using chiral iodoarenes as catalysts also gave promising results for some of the substrates.

mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives

A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.

A 1,3,2-Diazaphospholene-Catalyzed Reductive Claisen Rearrangement

1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.