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
• Uses: (1R)-(+)-Nopinone is a reagent used in the preparation of chiral ligands for asymmetric catalysis and transformations.

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:

3-Methoxalyl-6,6-dimethyl-bicyclo<3.1.1>heptan-3-on

(1R,5R)-6,6-Dimethyl-2-<(trimethylsilyl)oxy>bicyclo<3.1.1>hept-2-ene

2-[(1R,5S)-6,6-Dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-1-(2-hydroxy-4,6-dimethoxy-phenyl)-ethanone

2,3-dihydro-5,7-dimethoxy-2-(6,6-dimethylbicyclo<3.1.1.>-2-heptylidene)-4H-1-benzopyran-4-one

Refernces

• 1、 Chang, Wen-Sheng,Shia, Kak-Shan,Liu, Hsing-Jang,Wei Ly, Tai. "The first total synthesis of xenitorins B and C: Assignment of absolute configuration". . p. 3751 - 3753. Retrieved 2006.
• 2、 Yang, Yi-Qin,Xu, Hai-Jun,Lan, Lan,Wang, Shi-Fa. "Synthesis and crystal structure of chiral (1R,5R)-3-arylidenopinones". . p. 7490 - 7494. Retrieved 2013.
• 3、 Hida, Takemasa,Kikuchi, Junko,Kakinuma, Makoto,Nogusa, Hideo. "Risk assessment and safety evaluation study for ozonolysis of i-pinene: Raw material of a novel prostaglandin D2 receptor antagonist S-5751". . p. 1485 - 1489. Retrieved 2010.
• 4、 Liao, Shengliang,Shang, Shibin,Shen, Minggui,Rao, Xiaoping,Si, Hongyan,Song, Jie,Song, Zhanqian. "One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (?)-β-pinene". . p. 1512 - 1515. Retrieved 2016.
• 5、 Buntasana, Supanat,Hayashi, Jun,Klumphu, Piyatida,Padungros, Panuwat,Saetung, Prakorn,Vilaivan, Tirayut. "Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant". supporting information. . Retrieved 2022/02/23.
• 6、 Upshur, Mary Alice,Vega, Marvin M.,Bé, Ariana Gray,Chase, Hilary M.,Zhang, Yue,Tuladhar, Aashish,Chase, Zizwe A.,Fu, Li,Ebben, Carlena J.,Wang, Zheming,Martin, Scot T.,Geiger, Franz M.,Thomson, Regan J.. "Synthesis and surface spectroscopy of α-pinene isotopologues and their corresponding secondary organic material". . p. 8390 - 8398. Retrieved 2019/09/30.