Nopinone

Base Information

• Chemical Name: Nopinone
• CAS No.: 38651-65-9
• Molecular Formula: C9H14 O
• Molecular Weight: 138.21
• Hs Code.: 2914299000
• European Community (EC) Number: 640-215-2
• UNII: G7O7RX0V01
• Nikkaji Number: J260.256C
• Metabolomics Workbench ID: 133195
• ChEMBL ID: CHEMBL3782017
• Mol file: 38651-65-9.mol

Synonyms:38651-65-9;(1R)-(+)-Nopinone;(1R,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one;(+)-Nopinone;G7O7RX0V01;UNII-G7O7RX0V01;(1R,5S)-NOPINONE;(R)-(+)-NOPINONE;NSC 250997;NSC-250997;Bicyclo(3.1.1)heptan-2-one, 6,6-dimethyl-, (1R)-;Norinone;(1R,5S)-6,6-dimethyl-Bicyclo[3.1.1]heptan-2-one;Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-, (1R,5S)-;(1R,5S)-6,6-DIMETHYLBICYCLO(3.1.1)HEPTAN-2-ONE;BICYCLO(3.1.1)HEPTAN-2-ONE, 6,6-DIMETHYL-, (1R,5S)-;(1R,5S)-(+)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one;SCHEMBL2388827;CHEMBL3782017;(1R)-(+)-Nopinone, 98%;AKOS016010310;E73992;EN300-303653;J-500368

Chemical Property of Nopinone

Chemical Property:

• Vapor Pressure: 0.402mmHg at 25°C
• Melting Point: -1°C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 196.3°Cat760mmHg
• Flash Point: 65.5°C
• PSA: 17.07000
• Density: 0.986g/cm³
• LogP: 2.01160
• Storage Temp.: Store at 2-8
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 181

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1R)-(+)-NOPINONE 98.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC(=O)C1C2)C
• Isomeric SMILES: CC1([C@H]2CCC(=O)[C@@H]1C2)C
• General Description: (1R)-(+)-Nopinone is a commercially available bicyclic ketone used as a key starting material in the synthesis of cannabinoid metabolites, including deuterated analogs. Its (1R)-enantiomeric form serves as a chiral building block in streamlined synthetic routes, enabling efficient production of intermediates with high optical purity. (1R)-(+)-NOPINONE's structural features make it valuable for preparative-scale applications in pharmaceutical and analytical chemistry, particularly in the study of tetrahydrocannabinol derivatives.

Technology Process of Nopinone

There total 37 articles about Nopinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (1R,5S)-(+)-nopinone (38651-65-9)

Guidance literature:

With dimethylsulfide; ozone;

DOI:10.1021/acs.jpca.6b01995

Reference yield: 75.0%

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (1R,5S)-(+)-nopinone (38651-65-9) + (1S,2S,5S)-(+)-6,6-dimethylbicyclo[3.1.1]heptane-2-carboxaldehyde (128301-02-0)

Guidance literature:

With Fe(bpmen)(OTf)2; dihydrogen peroxide; acetic acid; In acetonitrile; at 20 ℃; Concentration;

DOI:10.1016/j.tet.2013.02.013

Reference yield: 65.0%

Beta-pinene (177698-19-0,25719-60-2) → (1R,5S)-(+)-nopinone (38651-65-9)

Guidance literature:

With 2-(3-butenyl)pyridine; ozone; In dichloromethane; at -78 ℃; Inert atmosphere;

DOI:10.1021/ol300617r

upstream raw materials:

beta-pinene

(-)-nopinone enol acetate

(+)-cis-3-bromonopinone

(1R,2R,5S)-(-)-α-nopinol

Downstream raw materials:

2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

(1R,2R,5S)-(-)-α-nopinol

(-)-trans-nopinol

3,3,6,6-tetramethylbicyclo[3.1.1]heptan-2-one

Refernces

A concise methodology for the synthesis of (-)-Δ⁹-tetrahydrocannabinol and (-)-Δ⁹-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

10.1016/j.tet.2007.06.006

The research aims to develop an efficient and concise method for synthesizing metabolites of tetrahydrocannabinols (THC) and tetrahydrocannabivarin (THCV), including their deuterated forms, which are crucial for analyzing biological and toxicological samples. The study introduces a streamlined synthetic approach using commercially available starting materials, such as (+)-(1R)-nopinone, to obtain key intermediates in just four steps. The methodology employs an optimized Shapiro reaction and avoids undesirable oxidative conditions, resulting in significantly improved overall yields and high optical purity. The researchers successfully synthesized eight regiospecifically deuterated metabolites without deuterium scrambling or loss, demonstrating the method's efficiency and applicability for preparative-scale production. This work provides a valuable tool for future studies on the biological and toxicological effects of these compounds.

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