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
• Article Data: 45

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 
• 109-72-8 n-butyllithium 
• 88841-83-2 3-(Phenylseleno)-2-cyclohexen-1-one 
• 504-02-9 1,3-cylohexanedione 
• 56671-81-9 3-bromo-2-cyclohexen-1-one 
• 62269-48-1 3-[(trimethylsilyl)oxy]cyclohex-2-en-1-one 
• 5682-75-7 3-chloro-2-cyclohexenone 
• 930-68-7 cyclohexenone 
• 100111-92-0 (C₄H₉)(CH₃)2Zn^(1-)*Li⁽¹⁺⁾=(C₄H₉)(CH₃)2ZnLi 
• 1352617-27-6 3-butylcyclohex-1-enyl t-butyldimethylsilyl ether 
• 88116-46-5 1-butyl-2-cyclohexen-1-ol 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 16807-60-6 3-methoxycyclohex-2-en-1-one 

Downstream Products

• 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.).

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.