40724-67-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-Ketopinic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its chiral nature allows for the creation of enantiomerically pure products, which is crucial for the development of effective and safe medications.
Used in Chiral Ligands Synthesis:
(S)-(+)-Ketopinic acid is used as a starting material for the preparation of chiral phosphine-oxazoline ligands. These ligands are essential in asymmetric palladium-catalyzed Heck reactions of aryl or alkenyl triflates with cyclic alkenes, which are important for the synthesis of complex organic molecules with potential applications in various industries.
Used in Catalysts for Asymmetric Reactions:
(S)-(+)-Ketopinic acid is used in the synthesis of chiral imino-phosphine ligands, which are crucial for palladium-catalyzed asymmetric Diels-Alder reactions. These reactions are employed to prepare six-membered carbocycles, which are vital components in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Copper-Catalyzed Henry (Nitro Aldol) Reactions:
(S)-(+)-Ketopinic acid is also used in the preparation of chiral iminopyridine ligands, which are employed in copper-catalyzed Henry (nitro aldol) reactions between nitromethane and o-anisol. This reaction is an essential step in the synthesis of β-hydroxynitroalkanes, which are valuable building blocks for the development of various pharmaceuticals and other organic compounds.

InChI:InChI=1/C10H14O3/c1-9(2)6-3-4-10(9,8(12)13)7(11)5-6/h6H,3-5H2,1-2H3,(H,12,13)/t6-,10+/m1/s1

Upstream product

• 86023-73-6 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carbaldehyde 
• 1925-51-5 (1R,4R)-1-hydroxymethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 
• 21286-54-4 Camphorsulfonyl chloride 
• 125637-45-8 (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid methylester 
• 20440-75-9 (+/-)-exo-2-hydroxy-bornan-10-oic acid 
• 107153-26-4 (+/-)-2exo-acetoxy-bornanoic acid-⁽¹⁰⁾ 
• 1925-53-7 (1R,4R)-10-acetoxycamphor 
• 64161-50-8 (1S,4R)-1-(bromomethyl)-7,7-dimethylbicyclo-[2.2.1]heptan-2-one 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 459124-78-8 (1R,4S)-2-[(1'S,4'R)-2-oxo-1-bornylcarbonyl]-2-aza-3-oxabicyclo[3.2.2]-8-nonene 
• 459124-75-5 (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid hydroxyamide 
• 850635-22-2 (+)-(1S,4R)-1-(1-chlorovinyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one 
• 459124-79-9 (1S,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbaldehyde 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Downstream Products

• 108176-17-6 (1R)-7,7-dimethyl-1-phenylbicyclo<2.2.1>heptan-2-one 
• 263722-70-9 7,7-dimethyl-2'-N-phenylhydrazine-bicyclo[2.2.1]heptane-1-carboxylic acid 
• 289722-43-6 (1S)-Ketopinoyl fluoride 
• 536-50-5 (S)-1-(4-Methylphenyl)ethanol 
• 42070-92-8 (R)-1-(4-methylphenyl)ethanol 
• 67252-79-3 (-)(S)-3-Methyl-1-phenyl-2-butanol 
• 63674-19-1 (R)-3-Methyl-1-phenyl-2-butanol 
• 27544-18-9 (S)-1-(2-Naphthyl)ethanol 
• 52193-85-8 (R)-1-(2-Naphthyl)ethanol 
• 1517-63-1 (R)-(4-Methylphenyl)phenylmethanol 
• 24218-12-0 (S)-(4-Methylphenyl)phenylmethanol 
• 4221-99-2 (S)-2-butanol 
• 14898-79-4 (2R)-butan-2-ol 
• 459124-75-5 (1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid hydroxyamide 

Relevant academic research and scientific papers

Switch in asymmetric induction sense in cycloadditions using camphor-based nitroso dienophiles

We have observed a unique reversal in the absolute stereochemistry of the principal adducts from the cycloadditions of camphor-based acylnitroso dienophiles as compared to the adducts obtained through reactions of the corresponding camphor-based chloronitroso compounds.

Novel O-acylated amidoximes and substituted 1,2,4-oxadiazoles synthesised from (+)-ketopinic acid possessing potent virus-inhibiting activity against phylogenetically distinct influenza A viruses

This article describes the synthesis and antiviral activity evaluation of new substituted 1,2,4-oxadiazoles containing a bicyclic substituent at position 5 of the heterocycle and O-acylated amidoximes as precursors for their synthesis. New compounds were

Novel bispidine-monoterpene conjugates—Synthesis and application as ligands for the catalytic ethylation of chalcones

A number of new chiral bispidines containing monoterpenoid fragments have been ob-tained. The bispidines were studied as ligands for Ni-catalyzed addition of diethylzinc to chalcones. The conditions for chromatographic analysis by HPLC-UV were developed,

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

NOVEL ARYLATED CAMPHENES, PROCESSES FOR THEIR PREPARATION AND USES THEREOF

The present invention relates to arylated camphenes, processes for their preparation and uses thereof for the manufacture of medicaments for the treatment of diseases, disorders or conditions associated with, or benefiting from stimulation of CB2 receptor

Synthesis of novel chiral Schiff bases and their application in asymmetric transfer hydrogenation of prochiral ketones

Novel chiral Schiff bases were synthesized from (+)-camphor, and their application to asymmetric transfer hydrogenation of prochiral ketones is described. The asymmetric transfer hydrogenation reaction could afford excellent conversion rates (up to 97.3%) and up to 27.3% enantiomeric excess.

1,2,3,4-Tetrahydro-1-naphthyl ester as a selective protecting group for carboxylic acids

The carboxylic acid functionality can be protected as the 1,2,3,4- tetrahydro-1-naphthyl ester, which can be selectively cleaved in the presence of aryl and alkyl esters using chlorotrimethylsilane and sodium iodide in acetonitrile. This protecting group allows room temperature deprotection under essentially neutral conditions throughout the cleavage reaction.

Synthesis and crystal structure of N-[(1S,4R)-2-oxo-pinanyl]-β-alanine methylester

The title compound, N-[(1S,4R)-2-oxo-pinanyl]-β-alanine methylester, is an important starting material for the electrochemical preparation of chiral amidoalkylation reagents in the synthesis of chiral β-substituted β-amino acid derivatives. The investigation of its crystal structure reveals an arrangement of the carbonyl group and the amine function, which is influenced by a hydrogen bonding interaction. This conformation makes the molecule especially appropriate for further synthetical modification.

Synthesis of several novel optically active nitroxyl radicals

Optically active nitroxyl radicals are prepared from enantiomerically pure bicyclic tempenoids. (-)-Camphoxyl radical (-)-4 derived from commercially available oxazolidinone (-)-1 and (+)-camphoxyl radical (+)-4 derived from (-)-camphene are readily prepared, conformationally rigid, enantiomeric nitroxyl radicals. (-)-Camphorsulphonic acid is used to prepare two additional optically active nitroxyl radicals 9 and 12.