80434-59-9

Basic information

• Product Name: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-
• CAS NO: 80434-59-9
• Molecular Formula: C11H20O
• Molecular Weight: 168.279
• Mol File: 80434-59-9.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-(80434-59-9)
• EPA Substance Registry System: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-(80434-59-9)

Safety Data

• Hazardous Substances Data: 80434-59-9(Hazardous Substances Data)

Upstream product

• 184178-86-7 (1S,4S,7R)-4-isopropyl-7-methyl-1-oxaspiro[2.5]octane 
• 104012-59-1 (+)-p-menth-3-ylchloride 
• 68-12-2 N,N-dimethyl-formamide 
• 10458-14-7 (2R,5S)-menthone 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 80447-43-4 (2S,5R)-1-Methoxymethylen-2-isopropyl-5-methylcyclohexan 
• 289909-56-4 tert-Butyl-[(E)-(R)-4-isopropyl-6-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-4-methyl-hex-5-enyloxy]-dimethyl-silane 
• 1217664-77-1 (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carbonitrile 
• 142921-58-2 (1S,2R,5S)-(+)-menthol Mesylate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 

Downstream Products

• 485843-44-5 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxaldehyde 
• 62309-29-9 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 108235-79-6 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carbonyl chloride 
• 289909-51-9 (E)-(S)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-hept-2-en-1-ol 
• 289909-79-1 (E)-(R)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-hept-2-en-1-ol 
• 474380-45-5 (E)-(S)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-oct-2-en-1-ol 
• 474380-58-0 (E)-(R)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-oct-2-en-1-ol 
• 16052-40-7 (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid 
• 289909-47-3 (E)-(S)-3-Cyclohexyl-1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-but-2-en-1-ol 
• 289909-70-2 (E)-(R)-3-Cyclohexyl-1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-but-2-en-1-ol 
• 289909-48-4 (S,E)-3-benzyl-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-2-en-1-ol 
• 289909-72-4 (R,E)-3-benzyl-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-2-en-1-ol 
• 868744-82-5 (R,E)-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4,4-dimethylpent-2-en-1-ol 
• 289909-49-5 (S,E)-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-3-phenylbut-2-en-1-ol 

Relevant articles and documents

Zinc-Mediated Hydroxyallylation of Aldehydes with Cyclopropanols: Direct Access to Vicinal anti-sec,tert-Diols via Enolized Homoenolates

Direct and diastereoselective synthesis of vicinal anti-sec,tert-diols has been achieved by zinc-mediated α-hydroxyallylation of aldehydes with cyclopropanols. The reaction features the action of the zinc-enolized homoenolate as a γ-oxyallyl nucleophile toward the carbonyl electrophile. The diastereoselectivity of the present reaction is ascribed to the strong preference for a chelated (Z)-configuration of the enolized homoenolate as well as the bicyclic chairlike transition state it forms with the aldehyde, where the aldehyde substituent prefers to occupy the pseudoaxial position.

Constraining the Side Chain of C-Terminal Amino Acids in Apelin-13 Greatly Increases Affinity, Modulates Signaling, and Improves the Pharmacokinetic Profile

Side-chain-constrained amino acids are useful tools to modulate the biological properties of peptides. In this study, we applied side-chain constraints to apelin-13 (Ape13) by substituting the Pro12 and Phe13 positions, affecting the binding affinity and signaling profile on the apelin receptor (APJ). The residues 1Nal, Trp, and Aia were found to be beneficial substitutions for Pro12, and the resulting analogues displayed high affinity for APJ (Ki 0.08-0.18 nM vs Ape13 Ki 0.7 nM). Besides, constrained (d-Tic) or α,α-disubstituted residues (Dbzg; d-α-Me-Tyr(OBn)) were favorable for the Phe13 position. Compounds 47 (Pro12-Phe13 replaced by Aia-Phe, Ki 0.08 nM) and 53 (Pro12-Phe13 replaced by 1Nal-Dbzg, Ki 0.08 nM) are the most potent Ape13 analogues activating the Gα12 pathways (53, EC50 Gα12 2.8 nM vs Ape13, EC50 43 nM) known to date, displaying high affinity, resistance to ACE2 cleavage as well as improved pharmacokinetics in vitro (t1/2 5.8-7.3 h in rat plasma) and in vivo.

Synthesis, characterization and hplc analysis of the (1S,2S,5R)-diastereomer and the enantiomer of the clinical candidate ar-15512

AR-15512 (formerly known as AVX-012 and WS-12) is a TRPM8 receptor agonist currently in phase 2b clinical trials for the treatment of dry eye. This bioactive compound with menthol-like cooling activity has three stereogenic centers, and its final structure and absolute configuration, (1R,2S,5R), have been previously solved by cryo-electron microscopy. The route of synthesis of AR-15512 has also been reported, revealing that epimerization processes at the C-1 can occur at specific stages of the synthesis. In order to confirm that the desired configuration of AR-15512 does not change throughout the process and to discard the presence of the enantiomer in the final product due to possible contamination of the initial starting material, both the enantiomer of AR-15512 and the diastereomer at the C-1 were synthesized and fully characterized. In addition, the absolute configuration of the (1S,2S,5R)-diastereomer was determined by X-ray crystallographic analysis, and new HPLC methods were designed and developed for the identification of the two stereoisomers and their comparison with the clinical candidate AR-15512.

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COMPOUNDS USEFUL AS MODULATORS OF TRPM8

The present invention includes compounds useful as modulators of TRPM8, such as compounds of Formulae (Ia), (Ib) and (Ic), and the subgenus and species thereof; personal products containing those compounds; and the use of those compounds and the personal products, particularly the use of increasing or inducing chemesthetic sensations, such as cooling or cold sensations.

PROCESS FOR MAKING NEO-ENRICHED p-MENTHANE COMPOUNDS

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Process for making neo-enriched p-menthane compounds

A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.

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A novel method to generate chiral quaternary carbon centers of high enantiomeric purity using a highly stereoselective addition of vinylalanes to a chiral aldehyde

The anti addition of cyanocuprates to chiral pivalates 2 derived from aldehyde 1 generates aldehydes 3 with a chiral quaternary carbon center. The generation of the alcohol precursors was achieved by a highly stereoselective addition of vinylalanes on the aldehyde auxiliary. Piv = pivaloyl = 2,2- dimethylpropyl.