40724-67-2

Basic information

• Product Name: (S)-(+)-KETOPINIC ACID
• Synonyms: (S)-7,7-DIMETHYL-2-OXO-BICYCLO[2.2.1]HEPTANE-1-CARBOXYLIC ACID;(S)-(+)-KETOPINIC ACID;(1S)-(+)-KETOPINIC ACID;(1S)-(+)-KETOPINIC ACID 97+%;(1s)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid;Bicyclo[2.2.1]heptane-1-carboxylic acid, 7,7-dimethyl-2-oxo-, (1S,4R)-;rac-(1S*,4R*)-2-Oxobornane-10-oic acid;(1S,4R)-2-Oxobornane-10-oic acid
• CAS NO: 40724-67-2
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• Product Categories: Chiral Reagents;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Synthetic Organic Chemistry;Terpenes
• Mol File: 40724-67-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 237-239 °C(lit.)
• Boiling Point: 313.3 °C at 760 mmHg
• Flash Point: 157.5 °C
• Appearance: /
• Density: 1.238 g/cm³
• Vapor Pressure: 0.000109mmHg at 25°C
• Refractive Index: 25.5 ° (C=0.65, MeOH)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.67±0.40(Predicted)
• BRN: 4180005
• CAS DataBase Reference: (S)-(+)-KETOPINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-KETOPINIC ACID(40724-67-2)
• EPA Substance Registry System: (S)-(+)-KETOPINIC ACID(40724-67-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 40724-67-2(Hazardous Substances Data)

Usage

Uses

(1S)-(+)-Ketopinic acid may be used to prepare:Chiral phosphine-oxazoline ligands, which can used in asymmetric palladium-catalyzed Heck reaction of aryl or alkenyl triflates with cyclic alkenes.A chiral imino-phosphine ligand, which can be used in palladium-catalyzed asymmetric Diels–Alder reactions to prepare six-membered carbocycles.A chiral iminopyridine ligand, which can be used in copper-catalyzed Henry (nitro aldol) reaction between nitromethane and o-anisol to form the corresponding β-hydroxynitroalkane.

General Description

(1S)-(+)-Ketopinic acid is a chiral ketone.

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

• 459124-79-9 (1S,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbaldehyde 
• 107153-26-4 (+/-)-2exo-acetoxy-bornanoic acid-⁽¹⁰⁾ 
• 20440-75-9 (+/-)-exo-2-hydroxy-bornan-10-oic acid 
• 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 
• 53585-70-9 (+)-7,7-dimethyl-1-vinyl-2-norbornanone 
• 850635-22-2 (+)-(1S,4R)-1-(1-chlorovinyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one 
• 125637-45-8 (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid methylester 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 21286-54-4 Camphorsulfonyl chloride 
• 1925-51-5 (1R,4R)-1-hydroxymethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 

Downstream Products

• 108176-17-6 (1R)-7,7-dimethyl-1-phenylbicyclo<2.2.1>heptan-2-one 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 865439-02-7 (S)-(2-benzylhydrazono)-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acid 
• 876760-56-4 2-(2-tosylhydrazono)-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acid 
• 363158-65-0 (1R,2R,4R)-1-Ethylaminomethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 363158-68-3 (1R,2R,4R)-1-(Benzylamino-methyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 1367830-85-0 (1S,4R)-1-{[4-(2-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-one 
• 1367830-73-6 (1S,2R,4R)-1-{[4-(2-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-ol 
• 1367830-87-2 (1S,4R)-1-{[4-(3-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-one 
• 1367830-76-9 (1S,2R,4R)-1-{[4-(3-hydroxyphenyl)piperazin-1-yl]carbonyl}-7,7-dimethylnorbornan-2-o 
• 182863-77-0 (R)-2-(2,2-dimethyl-3-oxocyclopentyl)acetonitrile 

Relevant articles and documents

Synthesis of (+)-(1S,4R)-1-(1-chlorovinyl)-7,7-dimethyl-bicyclo[2.2.1] heptan-2-one

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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

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.

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.