Hydrocinchonine

Base Information

• Chemical Name: Hydrocinchonine
• CAS No.: 485-65-4
• Molecular Formula: C19H24N2O
• Molecular Weight: 296.412
• European Community (EC) Number: 207-620-2,207-621-8
• Nikkaji Number: J3.324.348K
• Metabolomics Workbench ID: 44304
• ChEMBL ID: CHEMBL428695
• Mol file: 485-65-4.mol

Synonyms:Hydrocinchonine;GNF-PF-4292;(5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)-quinolin-4-ylmethanol;485-64-3;CHEMBL428695;Cinchotine;Pseudocinchonine;{5-ethyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol;(9S)-10,11-Dihydrocinchonan-9-ol;10,11-dihydrocinchonine;Cinchonifine;y-Cinchonine;Oprea1_425428;SCHEMBL312806;WFJNHVWTKZUUTR-UHFFFAOYSA-N;BCP18345;BCP18349;BDBM50047001;4-ETHYLAMINO-3-NITRO-BENZOICACID;Dihydrocinchonine;Hydrocinchonine, (+)-;NCGC00142479-01;AC-30196;(9S)-10,11-Dihydrocinchonan-9-ol, 9CI;FT-0700733;(5-Ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol

Chemical Property of Hydrocinchonine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 269-272 °C
• Refractive Index: 1.639
• Boiling Point: 467.126 °C at 760 mmHg
• PKA: 12.98±0.20(Predicted)
• Flash Point: 236.309 °C
• PSA: 36.36000
• Density: 1.18 g/cm³
• LogP: 3.32650
• Water Solubility.: 768.6mg/L(25 oC)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 296.188863393
• Heavy Atom Count: 22
• Complexity: 388

Purity/Quality:

99% ^*data from raw suppliers

Hydrocinchonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
• Uses: Hydrocinchonin is used in the enantioselective hydrogenation of α-ketoesters and the enantioselective synthesis of functionalized α-aminophosphonic acid derivatives.

Technology Process of Hydrocinchonine

There total 22 articles about Hydrocinchonine 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: 97.0%

cinchonine (118-10-5,485-70-1,485-71-2,550-54-9,40134-63-2,72402-55-2,72402-56-3) → 10,11-dihydrocinchonine (485-65-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 48h;

DOI:10.1039/c9ob01379b

Reference yield: 92.0%

Cinchonin (118-10-5) → dihydrocinchonine (485-65-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 10h;

DOI:10.1002/ejoc.201001175

Reference yield:

1-[(3R,4S)-3-Ethyl-4-(3-quinolin-4-yl-oxiranylmethyl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone (109922-61-4,109959-06-0) → dihydrocinchonine (485-65-4) + (-)-hydrocinchonidine (485-64-3)

Guidance literature:

With potassium carbonate; Yield given. Multistep reaction. Yields of byproduct given; 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h;

DOI:10.1016/S0040-4039(00)85384-8

upstream raw materials:

Cinchonin

4-((S)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(hydroxy)methyl)quinolin-6-ol

1-[(3R,4S)-3-Ethyl-4-(3-quinolin-4-yl-oxiranylmethyl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone

ethanol

Downstream raw materials:

C₆H₄NCH₂CHCCH₂

3,4-diethyl-pyridine

hydrocinchonine

(-)-hydrocinchonidine

Refernces

• 1、 Erlenmeyer. "-". . p. 731,742, 743, 746, 747. Retrieved 1930.
• 2、 Wu, Haotian,Hintermann, Lukas. "Transfer hydrogenations of alkenes with formate on Pd/C: Synthesis of dihydrocinchona alkaloids". . p. 888 - 892. Retrieved 2013/05/09.
• 3、 Kim, Sung Jun,Jang, Doo Ok. "Indium-mediated catalytic enantioselective allylation of N -benzoylhydrazones using a protonated chiral amine". supporting information; experimental part. p. 12168 - 12169. Retrieved 2010/10/03.