Quinuclidin-3-one

Base Information

• Chemical Name: Quinuclidin-3-one
• CAS No.: 3731-38-2
• Deprecated CAS: 29924-73-0,82737-04-0,82737-04-0
• Molecular Formula: C7H11 N O
• Molecular Weight: 125.17
• Hs Code.: 29333990
• European Community (EC) Number: 223-087-9
• NSC Number: 168448
• UNII: P4VF4G5PTA
• DSSTox Substance ID: DTXSID0063151
• Nikkaji Number: J2.861.961H,J100.532D
• Wikidata: Q72506084
• ChEMBL ID: CHEMBL377716
• Mol file: 3731-38-2.mol

Synonyms:3-quinuclidinone;quinuclidin-3-one

Chemical Property of Quinuclidin-3-one

Chemical Property:

• Melting Point: 200 °C
• Boiling Point: 204.9°Cat760mmHg
• PKA: 6.73±0.20(Predicted)
• Flash Point: 78.1°C
• PSA: 20.31000
• Density: 1.12g/cm³
• LogP: 0.21900
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 125.084063974
• Heavy Atom Count: 9
• Complexity: 136

Purity/Quality:

99.9% ^*data from raw suppliers

1-Azabicyclo[2.2.2]octan-3-one >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1C(=O)C2
• Uses: 3-Quinuclidinone is used in preparation of Maropitant.

Technology Process of Quinuclidin-3-one

There total 13 articles about Quinuclidin-3-one 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: 100.0%

3-quinuclidinone hydrochloride (1193-65-3) → 3-Quinuclidinone (3731-38-2)

Guidance literature:

With sodium carbonate; sodium hydroxide; In water; at 0 ℃; for 0.5h;

DOI:10.1107/S2053229619005898

Reference yield: 95.0%

3-quinuclidinol (1619-34-7) → 3-Quinuclidinone (3731-38-2)

Guidance literature:

With potassium tert-butylate; C₂₉H₃₀ClNOP₂Ru⁽¹⁺⁾; In acetone; at 60 ℃; for 10h; Product distribution / selectivity; Inert atmosphere;

Reference yield: 87.0%

(S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7) → 3-Quinuclidinone (3731-38-2)

Guidance literature:

With di-isopropyl azodicarboxylate; 9-azanoradamantane N-oxyl; acetic acid; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1021/jo300088b

upstream raw materials:

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate

Quinuclidine

3-<(N-benzyl)acetamido>quinuclidine

(S)-quinuclidin-3-ol

Downstream raw materials:

3-methylquinuclidin-3-ol

(Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one

3-phenyl-quinuclidin-3-ol

3-(4-dimethylamino-phenyl)-quinuclidin-3-ol

Refernces

• 1、 Qiao, Liang,Chen, Xiao-Gang,Gao, Ji-Xing,Ai, Yong. "Three new quinuclidine-based structures: Second harmonic generation response for 1,2-bis(1-azoniabicyclo[2.2.2]octan-3-ylidene)-hydrazine dichloride". . p. 728 - 733. Retrieved 2019.
• 2、 Wei, Zheyu,Ru, Shi,Zhao, Qixin,Yu, Han,Zhang, Gang,Wei, Yongge. "Highly efficient and practical aerobic oxidation of alcohols by inorganic-ligand supported copper catalysis". supporting information. p. 4069 - 4075. Retrieved 2019/08/07.