4481-78-1

Usage

InChI:InChI=1/C10H16O2/c11-9-5-4-8-10(12-9)6-2-1-3-7-10/h1-8H2

Upstream product

• 108-55-4 glutaric anhydride, 
• 23708-48-7 pentamethylenebis(magnesium bromide) 
• 57740-07-5 1-(4-hydroxybutyl)cyclohexan-1-ol 
• 16133-73-6 1-(pent-4-enyl)cyclohexanol 
• 91420-54-1 4-(1-Hydroxy-cyclohexyl)-butyric acid tert-butyl ester 
• 138719-72-9 2-Methoxy-1-oxaspiro<5.5>undecane 
• 201230-82-2 carbon monoxide 
• 6244-44-6 trans-1-(1-propenyl)cyclohexanol 
• 124-38-9 carbon dioxide 
• 195154-38-2 1-(3-Phenylsulfanyl-propyl)-cyclohexanol 
• 1123-34-8 1-allyl-1-cyclohexanol 
• 79-10-7 acrylic acid 
• 108-94-1 cyclohexanone 
• 335645-38-0 2-(3-chloropropyl)-2-ethoxy-1,3-dioxolane 

Downstream Products

• 50639-01-5 4-(cyclohex-1-en-1-yl)butanal 
• 57740-07-5 1-(4-hydroxybutyl)cyclohexan-1-ol 
• 198637-27-3 non-8-ene-1,5-diol 

Relevant academic research and scientific papers

A novel synthesis of γ,δ-unsaturated aldehydes from α-formyl-γ-lactones

A preparatively useful one-step transformation of γ,γ- disubstituted α-formyl-γ-lactones into trisubstituted γ,δ-unsaturated aldehydes is described, by means of catalytic amounts of either AcOH or AcOEt in the vapor phase over a glass support. A mechanistic rationale is proposed. Copyright

Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI2 and H2O

Although simple aliphatic esters and lactones have long been thought to lie outside the reducing range of SmI2, activation of the lanthanide reagent by H2O allows some of these substrates to be manipulated in an unprecedented fashion. For example, the SmI2-H2O reducing system shows complete selectivity for the reduction of 6-membered lactones over other classes of lactones and esters. The kinetics of reduction has been studied using stopped-flow spectrophotometry. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron-transfer to the lactone carbonyl. The radical intermediates formed during lactone reduction with SmI2-H2O can be exploited in cyclizations to give cyclic ketone (or ketal) products with high diastereoselectivity. The cyclizations constitute the first examples of ester-alkene radical cyclizations in which the ester carbonyl acts as an acyl radical equivalent.

Masked ω-lithio ester enolates: Synthetic applications

The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4'-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ortho esters 14: the β-chloro OBO ester derivate generates the γ-lactones 15 and the γ-chloro OBO ester gives corresponding esters 8.

Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts

(Matrix presented) A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO2 showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.

Rhodium catalysed carbonylation of homoallylic alcohols to spiropyrans bearing quaternary centres

A convenient preparation of substituted-spiropyrans via rhodium catalysed hydroformylation of homoallylic alcohols, followed by a condensation sequence to form hemiacetals and 2,2,3,3-tetraalkyl-4[H]- pyrans, is described.

Synthesis and Applications of Tetrahydrofuran-Stable Substituted (3-Lithioxyalkyl)- and (4-Lithioxyalkyl)lithiums, Modified with Magnesium 2-Ethoxyethoxide

Substituted hydroxyalkyl phenyl sulfides 3 have been synthesized from the corresponding allylic or homoallylic alcohols 2. Regiospecific cleavage of the C - SPh bond of the sulfides 3 by lithium dispersion in tetrahydrofuran (THF) led to the synthesis of substituted (3-lithioxyalkyl)- and (4-lithioxyalkyl)lithiums 4, most of which share the ω carbon with a carbocyclic ring. The organolithiums were modified with magnesium 2-ethoxyethoxide in order to suppress their reactivity toward THF cleavage, thus offering the advantage of preparing storable ethereal solutions of certain types of (lithioxyalkyl)lithiums. This strategy appears to be of rather broad scope. The functionalized organolithiums prepared in this way react normally with electrophilic reagents with yields in the range 35-55%. Thus, carboxylations of 4 yielded lactones 5, some of which are natural products, while reactions of 4 with benzophenone and cyclic ketones yielded 1,4- and 1,5-diols 6 and 7, respectively.

A new synthesis of lactones from tertiary alkenylcarbinols by cobalt-catalyzed photocarbonylation under ambient conditions

In the presence of a Co catalyst, tertiary vinyl-, propenyl-, and allylcarbinols were chelatively cycloadded to carbon monoxide to produce lactones by xanthone-sensitized photoreaction in tetrahydrofuran, under CO at 1 atmosphere and at room temperature.At lower temperatures the isomerization of alkenyl-carbinols was suppressed and lactones were obtained with improved selectivity.The photoprocess was facilitated by addition of pyridine or hydrogen and retarded in presence of amines or phosphines.Mechanistic interpretations for the process and the accompanying effects are discussed.Key words: chelative carbonylation, photocarbonylation, carbonylation of olefins, lactones synthesis from alkenylalcohols.

A convenient synthesis of 1-oxaspiro[5.5]undecane derivatives

2-Hydroxy-1-oxaspiro[5.5]undec-3-en-5-one, which is derived from 1-(2-furyl)cyclohexan-1-ol, is used in a convenient synthesis of several 1-oxaspiro[5.5]undecane derivatives.

DIRECT SYNTHESIS OF δ-LACTONES FROM 2-(3-LITHIOPROPYL)-1,3-DIOXOLANE AND CARBONYL COMPOUNDS

The reaction of 2-(3-lithiopropyl)-1,3-dioxolane (2), prepared in situ by lithiation of the chloroacetal 1 with lithium naphthalenide at -78 deg C, with aldehydes and ketones followed by hydrolysis with hydrochloric acid and final oxidation with PCC or Jones reagent yields the corresponding δ-lactones 5.

The Key Role of Water in the Heterogeneous Permanganate Oxidation of ω-Hydroxy Alkenes

Potassium permanganate-copper sulphate in dichloromethane in the presence of a catalytic amount of water effects a smooth oxidative cyclization of ω-hydroxy alkenes to ω-lactones in good yields with the net loss of one or more carbon atoms in the procees.