38651-65-9

Basic information

• Product Name: (1R)-(+)-NOPINONE
• Synonyms: (1R)-(+)-NOPINONE;6,6-DIMETHYLBICYCLO[3.1.1]HEPTAN-2-ONE;(1R)-(+)-Norinone;(1R,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one;Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-, (1R)-;(1R,5S)-(+)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one 98%;(1R)-(+)-Nopinone 98%;(1R,5S)-(+)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one98%
• CAS NO: 38651-65-9
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.21
• Mol File: 38651-65-9.mol
• Article Data: 57

Chemical Properties

• Melting Point: -1°C
• Boiling Point: 209 °C(lit.)
• Flash Point: 167 °F
• Appearance: /
• Density: 0.981 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.402mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: Store at 2-8
• CAS DataBase Reference: (1R)-(+)-NOPINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(+)-NOPINONE(38651-65-9)
• EPA Substance Registry System: (1R)-(+)-NOPINONE(38651-65-9)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 38651-65-9(Hazardous Substances Data)

Usage

Description

(1R)-(+)-NOPINONE, also known as (1R)-(+)-α-isopropenyl-γ-butyrolactone, is an organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It is a chiral compound with a unique structure, featuring a lactone ring and an isopropenyl group, which makes it valuable in the field of asymmetric catalysis and chemical transformations.

Uses

Used in Pharmaceutical Industry:
(1R)-(+)-NOPINONE is used as a reagent for the preparation of chiral ligands, which are essential in asymmetric catalysis and transformations. These chiral ligands play a crucial role in the synthesis of enantiomerically pure compounds, which are often required for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Industry:
(1R)-(+)-NOPINONE is also used as a building block in the synthesis of various complex organic molecules, including natural products and bioactive compounds. Its unique structure allows for a wide range of chemical reactions, making it a versatile starting material for the development of new chemical entities with potential applications in various industries.

InChI:InChI=1/C9H14O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-7H,3-5H2,1-2H3/t6-,7-/m0/s1

Upstream product

• 18172-67-3 beta-pinene 
• 28239-05-6 (-)-nopinone enol acetate 
• 28239-06-7 (+)-cis-3-bromonopinone 
• 31147-63-4 (1R,2R,5S)-(-)-α-nopinol 
• 177698-19-0 Beta-pinene 
• 564-94-3 myrtenal 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 

Downstream Products

• 35408-04-9 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 
• 31147-63-4 (1R,2R,5S)-(-)-α-nopinol 
• 31147-64-5 (-)-trans-nopinol 
• 35938-26-2 3-Methoxalyl-6,6-dimethyl-bicyclo<3.1.1>heptan-3-on 
• 33698-57-6 2-methyl-octa-2,7-dien-4-one 
• 36203-40-4 3,3,6,6-tetramethylbicyclo[3.1.1]heptan-2-one 
• 145434-32-8 (1R,2R,5S)-6,6-Dimethyl-2-pyridin-2-yl-bicyclo[3.1.1]heptan-2-ol 
• 72453-33-9 (1R,5R)-6,6-Dimethyl-2-<(trimethylsilyl)oxy>bicyclo<3.1.1>hept-2-ene 
• 115481-66-8 2-[(1R,5S)-6,6-Dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-1-(2-hydroxy-4,6-dimethoxy-phenyl)-ethanone 
• 115510-71-9 2,3-dihydro-5,7-dimethoxy-2-(6,6-dimethylbicyclo<3.1.1.>-2-heptylidene)-4H-1-benzopyran-4-one 
• 115463-47-3 <1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one 
• 128261-63-2 (1R,3R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>heptane-2-one 
• 128301-59-7 (1R,3S,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>heptane-2-one 
• 74275-35-7 3α-methyl-d₃-nopinone 

Relevant articles and documents

Synthesis and antibacterial activity of pinanyl-2-amino pyrimidines

A new series of pinene-2-alkyl amino pyrimidines were synthesized from (-)-β-pinene. (+)-No-pinone was obtained from (-)-β-pinene by selective oxidation with potassium permanganate and it was reacted with aromatic aldehydes including benzaldehyde, p-methylbenzaldehyde, p-methoxylbenzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, p-nitrobenzaldehyde, p-fluorobenzaldehyde, o-chlorobenzaldehyde, m-nitrobenzaldehyde, o-vanillin and furfural catalyzed with alkali catalysts to get optically active 3-arylidenenopinones 2a-2l. Then in the alkali catalytic conditions, they were used to synthesize pinanyl-2-amino pyrimidines (3a-3l) with guanidine hydrochloride. The structures of the synthesized compounds were identified by 1H NMR, 13 C NMR, FT-IR, GC-MS and elemental analysis. The antimicrobial activity of the newly synthesized pinanyl-2-amino pyrimidines (3a-3l) was done against C. albicans, A. niger, G. tropicalis, E. coli, S. aureus, B. Subtilis and P. fluorescens. It has been observed that compounds 3a and 3g have strong inhibition effect against Candida albicans, 3g has strong inhibition effect against Aspergillus niger, while 3g also has strong inhibition effect against Candida tropicalis.

Sustainable terpene-based polyamides: Via anionic polymerization of a pinene-derived lactam

A sustainable lactam, which is derived from the renewable terpene β-pinene, is converted to polyamides via a convenient anionic ring-opening polymerization (ROP), which can be easily handled without the use of a costly catalyst. The resulting polyamides have prosperous thermal properties, which enable their future use as high-performance polymers.

Synthesis and study of the antimalarial cardamom peroxide

A full account of our previously disclosed synthesis of the monoterpene dimer cardamom peroxide is reported. Inspired by hypotheses regarding the potential biosynthetic origins of this natural product, several unproductive routes are also reported. The ch

(1R,5S)-(+)-nopinone of high enantiomeric purity

Commercial β-pinene of 87% ee can be upgraded to the 98+% ee level by simple treatment with silver perchlorate. A solid complex is obtained whose formation is more rapid when two like enantiomers are involved. Simple dissolution of this precipitate in water releases the enantio-enriched hydrocarbon from which (+)-nopinone of high enantiomeric purity is obtained via ozonolysis.

Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant

Aqueous-phase ozonolysis in the atmosphere is an important process during cloud and fog formation. Water in the atmosphere acts as both a reaction medium and a reductant during the ozonolysis. Inspired by the atmospheric aqueous-phase ozonolysis, we herein report the ozonolysis of alkenes in water assisted by surfactants. Several types of surfactants, including anionic, cationic, and nonionic surfactants, were investigated. Although most surfactants enhanced the solubility of alkenes in water, they also generated excessive foaming during the ozone bubbling, which led to the loss of products. Mitigation of the frothing was accomplished by using Coolade as a nonionic and low-foaming surfactant. Coolade-assisted ozonolysis of alkenes in water provided the desired carbonyl products in good yields and comparable to those achieved in organic solvents. During the ozonolysis reaction, water molecules trapped within the polyethylene glycol region of Coolade were proposed to intercept the Criegee intermediate to provide a hydroxy hydroperoxide intermediate. Decomposition of the hydroxy hydroperoxide led to formation of the carbonyl product without the need for a reductant typically required for the conventional ozonolysis using organic solvents. This study presents Coolade as an effective surfactant to improve the solubility of alkenes while mitigating frothing during the ozonolysis in water.

Synthesis and surface spectroscopy of α-pinene isotopologues and their corresponding secondary organic material

Atmospheric aerosol-cloud interactions remain among the least understood processes within the climate system, leaving large uncertainties in the prediction of future climates. In particular, the nature of the surfaces of aerosol particles formed from biogenic terpenes, such as α-pinene, is poorly understood despite the importance of surface phenomena in their formation, growth, radiative properties, and ultimate fate. Herein we report the coupling of a site-specific deuterium labeling strategy with vibrational sum frequency generation (SFG) spectroscopy to probe the surface C-H oscillators in α-pinene-derived secondary organic aerosol material (SOM) generated in an atmospheric flow tube reactor. Three α-pinene isotopologues with methylene bridge, bridgehead methine, allylic, and vinyl deuteration were synthesized and their vapor phase SFG spectra were compared to that of unlabeled α-pinene. Subsequent analysis of the SFG spectra of their corresponding SOM revealed that deuteration of the bridge methylene C-H oscillators present on the cyclobutane ring in α-pinene leads to a considerable signal intensity decrease (ca. 30-40%), meriting speculation that the cyclobutane moiety remains largely intact within the surface bound species present in the SOM formed upon α-pinene oxidation. These insights provide further clues as to the complexity of aerosol particle surfaces, and establish a framework for future investigations of the heterogeneous interactions between precursor terpenes and particle surfaces that lead to aerosol particle growth under dynamically changing conditions in the atmosphere.