39189-74-7

Usage

Uses

2-Heptylidenecyclopentanone is a common substance that is found in fragrances.

InChI:InChI=1/C12H20O/c1-2-3-4-5-6-8-11-9-7-10-12(11)13/h8H,2-7,9-10H2,1H3/b11-8+

Upstream product

• 111-71-7 heptanal 
• 120-92-3 cyclopentanone 
• 137-03-1 2-heptylcyclopentanone 
• 93430-30-9 2-(1-hydroxyheptyl)cyclopentanone 
• 930-30-3 cyclopent-2-enone 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 

Downstream Products

• 137-03-1 2-heptylcyclopentanone 

Relevant academic research and scientific papers

Synthesis and odor of optically active 2-n-hexyl- and 2-n-heptylcyclopentanone and the corresponding δ-lactones

Enantiomeric 2-n-hexyl- and 2-n-heptylcyclopentanones (3) and (4) have been synthesized by asymmetric hydrogenation of 2-n-hexylidene and 2-n-heptylidenecyclopentanones (1) and (2) with Ru2Cl4[p-tolyl-binap]2NEt3/sub

Method for performing aldol condensation reaction in micro-channel reactor

The invention relates to a method for performing an aldol condensation reaction in a micro-channel reactor. The aldol condensation reaction is performed in the micro-channel reactor under the action of a catalyst at 60 to 170 DEG C and 0 to 5 MPa in the situation that alpha-H aldehyde ketone and other aldoketones in molecules are in the molar ratio of 0.8-1.2:1. According to the aldol condensationreaction involved in a process provided by the invention, the reaction time is shortened by thousands of times; the raw material conversion rate and the product selectivity are improved by 15 percentat least. The process provided by the invention can realize instantaneous uniform mixing; the equivalence ratio of materials in a reaction process is reduced; the using amount of a catalyst in a reaction process is reduced; Cannizzaro side reactions and polymerization reactions are reduced. The process provided by the invention also reduces the use of some additional solvents so as to reduce theproduction cost; the process provided by the invention also improves the safety of a reaction process, so that the types of reactions are safer and more environment-friendly; meanwhile, the micro-channel reactor used by the process provided by the invention is small in occupied area and high in capacity, so that the production efficiency and the production capacity are greatly improved.

Method for synthesizing 2-heptyl cyclopantanone by using dimethylamine as catalyst

The invention discloses a method for synthesizing 2-heptyl cyclopantanone by using dimethylamine as a catalyst. The method comprises the following steps: in the presence of a dimethylamine catalyst, performing a reaction on cyclopentanone and n-heptylaldehyde for 8-10 hours at 60-80 DEG C, adding glacial acetic acid to enhance the reaction in the reaction process, after the reaction is completed, adjusting the pH value to be 6-7, adding methylbenzene, performing stirring at 100-120 DEG C till no water is generated any more, and finally performing washing and drying, thereby obtaining a finished product. Due to adoption of the dimethylamine catalyst, the reaction progress and the selectivity of the reaction can be controlled, the utilization rate of reactant atoms can be increased, and the purpose of high-efficiency productivity of an aldol reaction can be achieved.

ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS

The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.

A novel pyrrolidine imide catalyzed direct formation of α,β-unsaturated ketones from unmodified ketones and aldehydes

(Chemical Equation Presented) A method for direct, stereoselective preparation of (E)-α,β-unsaturated ketones from ketones and aldehydes, promoted by a novel pyrrolidine imide organocatalyst, has been developed in moderate to high yields. Unlike the Claisen-Schmidt condensation and Lewis acid catalyzed tandem aldol-dehydration processes, this method provides mild reaction conditions to access α,β-unsaturated ketones from simple, unmodified ketones.

A new lewis acid system palladium/TMSCl for Catalytic aldol condensation of aldehydes with ketones

Palladium on charcoal effectively catalyzed the aldol condensation reactions of different ketones with aldehydes in the presence of trimethylsilyl chloride (TMSCl). The following reactions were investigated: (1) aromatic aldehydes with cycloalkanones, (2) aromatic aldehydes with aromatic ketones, (3) cycloalkanones with aliphatic aldehydes, and (4) the self-condensation reactions of aliphatic aldehydes and cycloalkanones.

Process for producing 2-alkyl-2cyclopentenones

Industrially advantageous processes for producing a 2-alkyl-2-cyclopentenone in high yields starting from a 2-(1-hydroxyalkyl)cyclopentanone or a 2-alkylidenecyclopentanone, which are obtainable from a cyclopentanone and a carbonyl compound. A 2-(1-hydroxyalkyl)cyclopentanone represented by the following general formula (1): (wherein R1, R2, R3, R4, R5, R6 and R7 each independently represents hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have one or more substituents or an aromatic group which may have one or more substituents, and each of (1) R6 or R7 with R3 and (2) R6 or R7 with R4 or R5 may be together combined to form a ring which may have a double bond) is subjected to dehydrative isomerization in the presence of a bromine compound and/or an iodine compound.

Reactions of tin(IV) enolates obtained from O-stannyl ketyls under neutral free radical conditions

Under mild and neutral free radical conditions, an α,β-unsaturated ketone reacted with tributyltin hydride to produce an intermediate resonance-stabilized allylic O-stannyl ketyl. Upon subsequent hydrogen atom abstraction, a tin(IV) enolate was afforded which could be quenched with a variety of electrophiles and form new carbon-carbon bonds. Aldehydes react to produce aldol-type products and both intramolecular and intermolecular carbonyl addition reactions were investigated using this strategy. Using similar methodology, the tin(IV) enolate could be quenched in the presence of HMPA with various alkyl halides and α,β-unsaturated carbonyl compounds (Michael acceptors) to yield alkylated products in good yields. These reactions represent a very mild regioselective alternative to metal enolate formation which usually requires strong bases such as LDA or strongly reductive dissolving metal conditions to achieve success. New carbon skeletons for natural product synthesis can be readily constructed using this chemically neutral approach.

INTERMOLECULAR ALDOL REACTIONS VIA ALLYLIC O-STANNYL KETYLS

A mild and neutral free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate.A tin(IV)enolate, produced by subsequent hydrogen atom transver, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new α,β-unsaturated ketones with E/Z ratios up to > 100:1.

Conversion of 2-alkylcyclopentanones into 2-alkyl-2-cyclopentenones with hydrated ferric chloride and cupric chloride

Hydrated ferric chloride, FeCl3*6H2O, in a polar, hydroxylic solvent converted 2-alkylcyclopentanones directly into 2-alkyl-2-cyclopentenones on heating in the presence of air.Yields of isolated products were about 40 percent.The scope of the reaction is discussed.With cupric chloride, chloroketones were formed as intermediates, which could be dehydrochlorinated to 2-alkyl-2-cyclopentenones in similar yields.