6301-49-1

Basic information

• Product Name: 3-butylcyclohex-2-en-1-one
• CAS NO: 6301-49-1
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.2334
• Mol File: 6301-49-1.mol

Chemical Properties

• Boiling Point: 239.5°C at 760 mmHg
• Flash Point: 99°C
• Density: 0.923g/cm³
• Vapor Pressure: 0.0399mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: 3-butylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-butylcyclohex-2-en-1-one(6301-49-1)
• EPA Substance Registry System: 3-butylcyclohex-2-en-1-one(6301-49-1)

Safety Data

• Hazardous Substances Data: 6301-49-1(Hazardous Substances Data)

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 930-68-7 cyclohexenone 
• 109-72-8 n-butyllithium 
• 5682-75-7 3-chloro-2-cyclohexenone 
• 74056-08-9 3-(4-Bromobutyl)-2-cyclohexen-1-one 
• 109-65-9 1-bromo-butane 
• 163332-59-0 (3-Methoxy-cyclohex-1-enesulfonyl)-benzene 
• 693-04-9 butyl magnesium bromide 
• 16179-67-2 3-morpholin-4-yl-cyclohex-2-enone 
• 88841-83-2 3-(Phenylseleno)-2-cyclohexen-1-one 
• 504-02-9 1,3-cylohexanedione 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 74-85-1 ethene 

Downstream Products

• 123540-67-0 6-(carbethoxymethyl)-3-butyl-2-cyclohexen-1-one 
• 148300-21-4 3-n-butyl-3-(phenylthio)cyclohexanone 
• 6301-51-5 3-ethyl-1-butyl-cyclohexa-1,3-diene 
• 72746-41-9 (R)-3-butylcyclohexanone 
• 39178-69-3 (S)-3-butylcyclohexan-1-one 
• 1601389-46-1 (S)-3-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexan-1-one 
• 4074-43-5 m-butyl phenol 

Relevant articles and documents

Reaction of zirconacycles with 3-iodopropenoates and 3-iodocycloenones in the presence of CuCl: A new pathway for the formation of cyclopentadienes and spirocyclic compounds

Formation of cyclic compounds from zirconacycles has been performed by a combination of Michael addition and coupling with an alkenyl iodide moiety in the presence of a stoichiometric amount of CuCl. The reaction of 3- iodopropenoates with various zircona

Chemo-Enzymatic Oxidative Rearrangement of Tertiary Allylic Alcohols: Synthetic Application and Integration into a Cascade Process

A chemo-enzymatic catalytic system, comprised of Bobbitt's salt and laccase from Trametes versicolor, allowed the [1,3]-oxidative rearrangement of endocyclic allylic tertiary alcohols into the corresponding enones under an Oxygen atmosphere in aqueous media. The yields were in most cases quantitative, especially for the cyclopent-2-en-1-ol or the cyclohex-2-en-1-ol substrates without an electron withdrawing group (EWG) on the side chain. Transpositions of macrocyclic alkenols or tertiary alcohols bearing an EWG on the side chain were instead carried out in acetonitrile by using an immobilized laccase preparation. Dehydro-Jasmone, dehydro-Hedione, dehydro-Muscone and other fragrance precursors were directly prepared with this procedure, while a synthetic route was developed to easily transform a cyclopentenone derivative into trans-Magnolione and dehydro-Magnolione. The rearrangement of exocyclic allylic alcohols was tested as well, and a dynamic kinetic resolution was observed: α,β-unsaturated ketones with (E)-configuration and a high diastereomeric excess were synthesized. Finally, the 2,2,6,6-tetramethyl-1-piperidinium tetrafluoroborate (TEMPO+BF4?)/laccase catalysed oxidative rearrangement was combined with the ene-reductase/alcohol dehydrogenase cascade process in a one-pot three-step synthesis of cis or trans 3-methylcyclohexan-1-ol, in both cases with a high optical purity. (Figure presented.).

Total Synthesis of (-)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones

We report a total synthesis of the pyridine-containing limonoid alkaloid (-)-xylogranatopyridine B in 11 steps from commercially available dihydrocarvone. The central pyridine ring was assembled by a late-stage fragment coupling approach employing a modified Liebeskind pyridine synthesis. One fragment was prepared by an allyl-palladium catalyzed oxidative enone β-stannylation, in which the key bimetallic β-stannyl palladium enolate intermediate undergoes a β-hydride elimination. This methodology also allowed introduction of alkyl and silyl groups to the β-position of enones.

Preparation of o-Fluorophenols from Nonaromatic Precursors: Mechanistic Considerations for Adaptation to Fluorine-18 Radiolabeling

The preparation of fluorine-18 labeled o-fluorophenols at high specific activity is challenging and requires use of [18F]fluoride ion as the radioisotope source. As a novel, alternative approach, we found that treatment of α-diazocyclohexenones with Selectfluor and Et3N·3HF followed by HF elimination and tautomerization afforded o-fluorophenols regioselectively and rapidly. To adapt this chemistry to 18F radiolabeling, using bromine electrophiles in place of Selectfluor gave the o-fluorophenol via an α-bromo-α-fluoroketone intermediate in lower but still reasonable yields.

Novel PDC catalyzed oxidative rearrangement of tertiary allylic alcohols to β-substituted enones

Novel pyridinium dichromate (PDC) catalyzed oxidative rearrangement for the conversion of tertiary allylic alcohols to ?-substituted enones is described. Using a catalytic amount of PDC with PhI(OAc)2 as a co-oxidant in the presence of magnesium sulfate and water under oxygen was found effective for this rearrangement.

Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent

A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).

Oxidative conversion of silyl enol ethers to α,β-unsaturated ketones employing oxoammonium salts

The oxidative conversion of silyl enol ethers to α,β-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO +BF4-) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.

Pt-catalyzed oxidative rearrangement of cyclic tertiary allylic alcohols to enones using aqueous hydrogen peroxide

An oxidative rearrangement of cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by Pt black catalyst with aqueous hydrogen peroxide is described. The reaction proceeds under organic solvent- and halide-free conditions and gives only water as a coproduct. The Pt black catalyst is commercially available and can be reused at least four times.

Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO

Two methods for the oxidative rearrangement of tertiary allylic alcohols have been developed. Most of tertiary allylic alcohols studied were oxidized to their corresponding transposed carbonyl derivatives in excellent to fair yields by reaction with TEMPO in combination with PhIO and Bi(OTf)3 or copper (II) chloride in the presence or not of oxygen. Other primary oxidants of TEMPO such as PhI(OAc)2, mCPBA, and Oxone were unsatisfactory giving the enone in modest to low yields.

Copper-catalyzed aerobic oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO

A mild method for the oxidative rearrangement of tertiary allylic alcohols to β-substituted enones using a TEMPO/CuCl2 system, in the presence of molecular sieves, is described. Depending on the substrate, CuCl2 was used in either a catalytic amount under an oxygen atmosphere or stoichiometrically. Georg Thieme Verlag Stuttgart.