4361-28-8

Usage

Uses

Used in Organic Synthesis:
Cyclohexanepropionaldehyde is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable building block for the creation of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, cyclohexanepropionaldehyde is used as a starting material for the synthesis of various pharmaceutical compounds. Its reactivity and versatility make it a preferred choice for the development of new drugs and therapeutic agents.
Used in Fragrance Industry:
Cyclohexanepropionaldehyde is also utilized in the fragrance industry to create unique and complex scents. Its ability to undergo various chemical reactions allows for the creation of a wide range of aroma compounds, contributing to the diversity of fragrances available in the market.
Used in Chemical Research:
In the field of chemical research, cyclohexanepropionaldehyde serves as a model compound for studying various reaction mechanisms and exploring new synthetic pathways. Its unique properties make it an ideal candidate for understanding the behavior of similar compounds and developing new methodologies in organic chemistry.

InChI:InChI=1/C9H16O/c10-8-4-7-9-5-2-1-3-6-9/h8-9H,1-7H2

Upstream product

• 58474-99-0 3-cyclohexyl-propionaldehyde diethylacetal 
• 64-17-5 ethanol 
• 5664-17-5 cyclohexylallene 
• 695-12-5 vinylcyclohexane 
• 201230-82-2 carbon monoxide 
• 42134-55-4 3-cyclohexyl-2-propen-1-ol 
• 2114-42-3 allylcyclohexane 
• 37868-74-9 3-cyclohexyl-2-propenal 
• 20681-51-0 methyl 3-cyclohexylpropionate 
• 701-97-3 cyclohexanepropionic acid 
• 56453-86-2 (E)-3-cyclohexylprop-2-enoic acid 
• 1124-63-6 3-cyclohexylpropan-1-ol 
• 630-19-3 pivalaldehyde 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 125416-33-3 E-10-dicyclohexylsulfamoyl-D-isobornyl 4-hydroxy-5-cyclohexylpent-2-enoate 
• 125416-33-3 (E)-(R)-5-Cyclohexyl-4-hydroxy-pent-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 125473-41-8 (E)-(S)-5-Cyclohexyl-4-hydroxy-pent-2-enoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 56453-86-2 (E)-3-cyclohexylprop-2-enoic acid 
• 305816-16-4 3-cyclohexyl-1-(2-methoxy-3-methyl-6-trimethylsilanyl-pyridin-4-yl)-propan-1-ol 
• 303021-40-1 4-(2-cyclohexylethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]-pyridine 
• 1022985-47-2 (R)-2-(cyclohexylmethyl)-4-nitrobutanal 
• 1240493-23-5 C₂₂H₃₁N 
• 1384252-68-9 C₂₈H₄₂O₆ 
• 1384252-69-0 C₂₈H₄₂O₆ 
• 1431387-06-2 1,1,1,3,3,3-hexafluoropropan-2-yl 3-cyclohexylpropanoate 

Relevant academic research and scientific papers

Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide

The tripeptide H-dPro-Pro-Asn-NH2is presented as a catalyst for asymmetric conjugate addition reactions of aldehydes to maleimide. The peptidic catalyst promotes the reaction between various aldehydes and unprotected maleimide with high stereoselectivities and yields. The obtained products were readily derivatized to the corresponding pyrrolidines, lactams, lactones, and peptide-like compounds.1H NMR spectroscopic, crystallographic, and computational investigations provided insight into the conformational properties of H-dPro-Pro-Asn-NH2and revealed the importance of hydrogen bonding between the peptide and maleimide for catalyzing the stereoselective C?C bond formation.

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates

An efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B2pin2) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates with high efficiency and excellent stereoselectivity. Moreover, the borylated products, through versatile carbon–boron bond transformations, were readily converted into diverse synthetically useful molecules, including α-hydroxy ketones, functionalized SEEs, and gem-difunctionalized aldehydes.

Palladium/Copper-catalyzed Oxidation of Aliphatic Terminal Alkenes to Aldehydes Assisted by p-Benzoquinone

The development of an anti-Markovnikov Wacker-type oxidation for simple aliphatic alkenes is a significant challenge. Herein, a variety of aldehydes can be selectively obtained from various unbiased aliphatic terminal alkenes using PdCl2(MeCN)2/CuCl in the presence of p-benzoquinone (BQ) under mild reaction conditions. Isomerization of the terminal alkene to the internal alkene was suppressed via slow addition of the starting material to the reaction mixture. In addition to the Pd catalyst, CuCl and BQ were essential in order to obtain the anti-Markovnikov product with high selectivity. Terminal alkenes bearing a halogen substituent afforded their corresponding aldehydes with high anti-Markovnikov selectivity. The halogen acts as a directing group in the reaction. DFT calculations indicate that a μ-chloro Pd(II)?Cu(I) bimetallic species with BQ coordinated to Cu is the catalytically active species in the case of a terminal alkene without a directing group.

An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols

Structure-guided directed evolution of choline oxidase has been carried out by using the oxidation of hexan-1-ol to hexanal as the target reaction. A six-amino-acid variant was identified with a 20-fold increased kcat compared to that of the wild-type enzyme. This variant enabled the oxidation of 10 mm hexanol to hexanal in less than 24 h with 100 % conversion. Furthermore, this variant showed a marked increase in thermostability with a corresponding increase in Tm of 20 °C. Improved solvent tolerance was demonstrated with organic solvents including ethyl acetate, heptane and cyclohexane, thereby enabling improved conversions to the aldehyde by up to 30 % above conversion for the solvent-free system. Despite the evolution of choline oxidase towards hexan-1-ol, this new variant also showed increased specific activities (by up to 100-fold) for around 50 primary aliphatic, unsaturated, branched, cyclic, benzylic and halogenated alcohols.

TRICYCLIC COMPOUND SERVING AS IMMUNOMODULATOR

Provided are compounds of formula I and formula II or pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. The compounds of formula I and formula II or the pharmaceutically acceptable salts of the compounds provide indole 2,3-dioxygenase (IDO) inhibitory activity and are capable of treating IDO-mediated immunosuppressive diseases, such as infectious diseases or cancer.

An organocatalytic enantioselective direct α-heteroarylation of aldehydes with isoquinoline: N -oxides

A new protocol for the enantioselective direct α-heteroarylation of aldehydes with isoquinoline N-oxides, via chiral enamine catalysis, has been successfully developed. High enantiomeric excesses and moderate to good yields were achieved for a variety of α-heteroarylated aldehydes.

Novel synthetic approach to alfaprostol key intermediates via Stille coupling with an alkyne

Novel intermediates based on the Corey skeleton for preparation of the ω-chain of non-halogenated unnatural prostaglandin analogues containing a triple bond at position 13–14 (PG numbering) were synthesized. The utilization of a novel synthetic approach towards a new tin intermediate, and subsequent Stille coupling opens up new possibilities for preparing these important pharmaceutical intermediates.

Nucleophilic Dearomatization of Pyridines under Enamine Catalysis: Regio-, Diastereo-, and Enantioselective Addition of Aldehydes to Activated N-Alkylpyridinium Salts

Catalytic addition of chiral enamines to azinium salts is a powerful tool for the synthesis of enantioenriched heterocycles. An unprecedented asymmetric dearomative addition of aldehydes to activated N-alkylpyridinium salts is presented. The process exhibits complete C-4 regioselectivity along with high levels of diastereo- and enantiocontrol, achieving a high-yielding synthesis of a broad range of optically active 1,4-dihydropyridines. Moreover, the presented methodology enables the synthesis of functionalized octahydropyrrolo[2,3-c]pyridines, the core structure of anticancer peptidomimetics.

IMPROVED APELIN RECEPTOR (APJ) AGONISTS AND USES THEREOF

This disclosure is directed to agonists of the apelin receptor (APJ) and uses of such agonists.