Hydrocinchonidine

Base Information

• Chemical Name: Hydrocinchonidine
• CAS No.: 485-64-3
• Molecular Formula: C19H24 N2 O
• Molecular Weight: 296.412
• European Community (EC) Number: 207-620-2
• UNII: 8635CEW7CR
• DSSTox Substance ID: DTXSID001315486
• Wikidata: Q27269695
• ChEMBL ID: CHEMBL585986
• Mol file: 485-64-3.mol

Synonyms:Hydrocinchonidine;(8alpha,9R)-10,11-Dihydrocinchonan-9-ol;dihydrocinchonidine;UNII-8635CEW7CR;8635CEW7CR;485-64-3;(-)-dihydrocinchonidine;EINECS 207-620-2;GNF-Pf-1324;Cinchamidine;(8-alpha,9R)-10,11-Dihydrocinchonan-9-ol;HYDROCINCHONIDINE [MI];CHEMBL585986;SCHEMBL2404224;WFJNHVWTKZUUTR-KODHJQJWSA-N;DTXSID001315486;(3R,8S,9R)-10,11-Dihydrocinchonidine;(8|A,9R)-10,11-dihydro-Cinchonan-9-ol;CS-0091382;H1702;E78977;(8.ALPHA.,9R)-10,11-DIHYDROCINCHONAN-9-OL;Q27269695

Chemical Property of Hydrocinchonidine

Chemical Property:

• Melting Point: 230°
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 467.1°Cat760mmHg
• PKA: 12.98±0.20(Predicted)
• Flash Point: 236.3°C
• PSA: 36.36000
• Density: 1.18g/cm³
• LogP: 3.32650
• 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

Cinchamidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=CC=NC4=CC=CC=C34)O
• Uses: Cinchamidine, is an impurity of Quinine (Q694000). It is also a dihydro derivative of Cinchonine (C441925), an antimalarial agent.

Technology Process of Hydrocinchonidine

There total 19 articles about Hydrocinchonidine 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: 92.0%

Cinchonidin (485-71-2) → (-)-hydrocinchonidine (485-64-3)

Guidance literature:

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

DOI:10.1016/j.tet.2007.05.076

Reference yield: 86.8%

cinchonidine (118-10-5,485-70-1,485-71-2,550-54-9,40134-63-2,72402-55-2,72402-56-3) → 10,11-dihydrocinchonidine (485-64-3)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; under 750.06 Torr; Ambient temperature;

DOI:10.1006/jcat.1997.1925

Reference yield:

C6H4NCH2CHCCH2 (491-35-0) → (-)-hydrocinchonidine (485-64-3)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium diisopropylamide, pyridine hydrochloride

2: 90 percent / pyridine hydrochloride / methanol; pyridine; various solvent(s) / 36 h / Ambient temperature

3: 1) water 2.) NH4OAc, NaCNBH3 / 1) β-glucosidase / 2.) pH=6.2, 18 h

4: 1.) 3percent HCl, 2.) NaCNBH₃ / 1.) aq MeOH, reflux, 40 min

5: 2.) CF₃CO₃H, Na₂HPO₄ / 1.) 0 grad C, 2.) CH₂Cl₂, rt, 12 h

6: 1.) K₂CO₃ / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h

With hydrogenchloride; disodium hydrogenphosphate; trifluoroacetyl peroxide; ammonium acetate; water; pyridine hydrochloride; sodium cyanoborohydride; potassium carbonate; lithium diisopropyl amide; β-glucosidase; In pyridine; methanol;

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

upstream raw materials:

Cinchonidin

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

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

pentan-1-ol

Downstream raw materials:

C₆H₄NCH₂CHCCH₂

3,4-diethyl-pyridine

4-quinolinic acid

2,7-bis[O(9)-allylhydrocinchonidinium-N-methyl]naphthalene dibromide

Refernces

• 1、 Emde. "-". . p. 557,573. Retrieved 1932.
• 2、 Bartok, Mihaly,Balazsik, Katalin,Szoelloesi, Gyoergy,Bartok, Tibor. "Electrospray ionization-mass spectrometry in the enantioselective hydrogenation of ethyl pyruvate catalyzed by dihydrocinchonidine modified Pt/Al2O3 in acetic acid". . p. 168 - 176. Retrieved 2002.
• 3、 Nindakova,Strakhov,Kolesnikov. "Hydrogenation of Ketones on Dispersed Chiral-Modified Palladium Nanoparticles". . p. 199 - 207. Retrieved 2018/03/26.
• 4、 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.