18456-90-1

Basic information

• Product Name: 2-Butyl-1,3-cyclohexanedione
• Synonyms: 2-Butyl-1,3-cyclohexanedione
• CAS NO: 18456-90-1
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 0
• Mol File: 18456-90-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Butyl-1,3-cyclohexanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butyl-1,3-cyclohexanedione(18456-90-1)
• EPA Substance Registry System: 2-Butyl-1,3-cyclohexanedione(18456-90-1)

Safety Data

• Hazardous Substances Data: 18456-90-1(Hazardous Substances Data)

Upstream product

• 93919-00-7 ethyl 5-oxodecanoate 
• 504-02-9 1,3-cylohexanedione 
• 123-72-8 butyraldehyde 
• 63588-95-4 6-Butyl-1,5-dimethoxy-cyclohexa-1,4-diene 
• 110-62-3 pentanal 
• 10488-95-6 ethyl 3-oxooctanoate 
• 872804-89-2 ethyl 2-(2-cyanoethyl)-3-oxooctanoate 
• 60462-02-4 ethyl 2-acetyl-3-oxooctanoate 
• 6093-95-4 methyl 5-oxodecanoate 

Downstream Products

• 56459-18-8 2-butyl-3-ethoxy-2-cyclohexen-1-one 
• 56459-21-3 2-butyl-3-vinylcyclohex-2-en-1-one 
• 15289-04-0 1-phenyl-dec-5-yn-1-one 
• 1243555-23-8 C₁₂H₁₃ClO₃ 
• 1243555-22-7 C₁₃H₁₃ClO₄ 
• 102626-23-3 2,4-dichlorobenzene-1,3,5-tricarbaldehyde 
• 334-48-5 1-decanoic acid 
• 88367-24-2 2-butyl-3-(4-tetrahydropyranyloxybutyl)cyclohex-2-enone 
• 83562-29-2 2-Butyl-3-(4-hydroxybutyl)-2-cyclohexen-1-one 
• 21081-31-2 1-Phenylhydrazino-2-n-butyl-cyclohexen-⁽¹⁾-on-⁽³⁾ 

Relevant articles and documents

Design, synthesis and application of spiro[4.5]cyclohexadienonesviaone-pot sequentialp-hydroxybenzylation/oxidative dearomatization

One-pot sequentialp-hydroxybenzylation/oxidative dearomatization/spiroannulation has been designed for the efficient construction of tetrahydrofuran containing spiro-cyclohexadienones. This reaction proceeds through thep-hydroxybenzylation of 1,3-diketones withp-hydroxybenzyl alcoholviaquinone methide formation followed by oxidative dearomatization/spiroannulation with suitable alcohols. The Friedel-Crafts alkylation of spiro[4.5]cyclohexadienones with indoles provided a broad array of highly diastereoselective C-3 alkylated spirocycles and cyclohepta[b]indoles depending upon the ring size of the fused cyclic ketones.

A Formal Synthesis of (-)-Perhydrohistrionicotoxin Using a Cross Metathesis-Hydrogenation Approach

The development of an efficient, high yielding six-step convergent synthesis of the semisynthetic alkaloid (-)-perhydrohistrionicotoxin is described. The key transformations include the cross metathesis of a Br?nsted-acid masked primary homoallylic amine with a vinyl cyclohexenone and a regioselective palladium catalyzed hydrogenation. This sequence generated the advanced Winterfeldt spirocyclic precursor in 47% overall yield, with a longest linear sequence of five steps.

Enantioselective Palladium-Catalyzed Intramolecular α-Arylative Desymmetrization of 1,3-Diketones

An efficient enantioselective protocol has been reported to build highly oxygenated and densely substituted bicyclo[m.n.1] skeletons through intramolecular asymmetric α-arylative desymmetrization of 1,3-diketones. Employing Pd catalyst and FOXAP ligand, various bicyclo[m.n.1] skeleton with different size can be accessed with high enantio- and diastereoselectivities. Utilizing the present method as a key step, formal asymmetric total synthesis of the (-)-parvifoline has been demonstrated.

Hypervalent Activation as a Key Step for Dehydrogenative ortho C-C Coupling of Iodoarenes

Building on earlier results, a direct metal-free α- arylation of substituted cyclic 1,3-diones using ArI(O2CCF3)2 reagents has been developed; unlike other arylative approaches, the arylated products retain the iodine substituent ortho to the newly formed C-C bond. The mechanism is explored by using DFT calculations, which show a vanishingly small activation barrier for the C-C bond-forming step. In fact, taking advantage of an efficient in situ hypervalent activation, the iodoarenes are shown to undergo a cross- dehydrogenative C-C coupling at the C-H ortho to the iodine. When Oxone is used as terminal oxidant, the process is found to benefit from a rapid initial formation of the hypervalent ArI(OR)2 species and the sulfate-accelerated final coupling with a ketone. This method complements the ipso selectivity obtained in the metal-catalyzed α-arylation of carbonyl compounds.

Synthesis of chiloglottones - Semiochemicals from sexually deceptive orchids and their pollinators

A five-step synthesis of monoalkyl- and 2,5-dialkyl-1,3-cyclohexanediones (1) is described via a sequence involving sequential Birch reductions and alkylations from the readily accessible and inexpensive starting material, 3,5-dimethoxybenzoic acid. Two approaches were considered in which alkylation at C-2 occurs either prior or subsequent to the proposed reduction. The successful route, in which Birch reduction of a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed for their biological activity via electroantennographic detection.

Organocatalytic sequential one-pot double cascade asymmetric synthesis of Wieland-Miescher ketone analogues from a knoevenagel/hydrogenation/robinson annulation sequence: Scope and applications of organocatalytic biomimetic reductions

(Chemical Equation Presented) A practical and novel organocatalytic chemo- and enantioselective process for the cascade synthesis of highly substituted 2-alkyl-cyclohexane-1,3-diones and Wieland-Miescher (W-M) ketone analogs is presented via reductive alk

Synthesis of (+/-)-Depentylperhydrohistrionicotoxin

Palladium(0)-catalysed cyclisation of 3-acetoxy-1-(4-aminoalkyl)cyclohexenes provides convenient access to the 1-azaspiroundecane ring system found in the histrionicotoxins.Hydroboration of the 7-butyl derivative (4; R1 = Bun, R