Acetylquinine

Base Information

• Chemical Name: Acetylquinine
• CAS No.: 18797-86-9
• Molecular Formula: C22H26 N2 O3
• Molecular Weight: 366.46
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80940273
• Mol file: 18797-86-9.mol

Synonyms:acetylquinine

Chemical Property of Acetylquinine

Chemical Property:

• Vapor Pressure: 5.5E-10mmHg at 25°C
• Boiling Point: 496.2°Cat760mmHg
• Flash Point: 253.9°C
• PSA: 82.89000
• Density: 1.2g/cm³
• LogP: 3.20200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 366.19434270
• Heavy Atom Count: 27
• Complexity: 554

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-(6-Methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methylacetate 97%mixTBCasstabilizer ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C1CC2CCN1CC2C=C)C3=C4C=C(C=CC4=NC=C3)OC
• Isomeric SMILES: CC(=O)O[C@@H]([C@@H]1C[C@H]2CCN1C[C@@H]2C=C)C3=C4C=C(C=CC4=NC=C3)OC

Technology Process of Acetylquinine

There total 11 articles about Acetylquinine 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: 99.0%

acetic anhydride (108-24-7) + Quinine (130-95-0) → acetylquinine (18797-86-9,56652-53-0)

Guidance literature:

With phosphoric acid; In acetonitrile; at 50 ℃; for 21h;

DOI:10.1021/acs.joc.1c00102

Reference yield: 99.0%

quinine (130-95-0) + acetyl chloride (75-36-5) → (R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl acetate (18797-86-9)

Guidance literature:

With triethylamine;

DOI:10.1002/1521-3773(20011119)40:22<4214::AID-ANIE4214>3.0.CO;2-B

Reference yield: 88.0%

acetic anhydride (108-24-7) + quinine (130-95-0) → (R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl acetate (18797-86-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 21h; Inert atmosphere;

DOI:10.1021/jacs.6b01183

upstream raw materials:

acetic anhydride

Quinine

acetic acid

4-nitrophenol acetate

Downstream raw materials:

quinine

(R)-1-{(1S,3R,4S)-6-[(S)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethane-1,2-diol

(S)-1-{(1S,3R,4S)-6-[(S)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethane-1,2-diol

Refernces

• 1、 Hermann,Wynberg. "-". . p. 2208. Retrieved 1977.
• 2、 Hayashi, Hiroyuki,Yasukochi, Shotaro,Sakamoto, Tatsuhiro,Hatano, Manabu,Ishihara, Kazuaki. "Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives". . p. 5197 - 5212. Retrieved 2021/04/12.
• 3、 Hu, Bin,Bezpalko, Mark W.,Fei, Chao,Dickie, Diane A.,Foxman, Bruce M.,Deng, Li. "Origin of and a Solution for Uneven Efficiency by Cinchona Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions". supporting information. p. 13913 - 13920. Retrieved 2018/10/20.