Dihydroquinine

Base Information

• Chemical Name: Dihydroquinine
• CAS No.: 522-66-7
• Molecular Formula: C20H26N2O2
• Molecular Weight: 326.439
• Hs Code.: 29339900
• European Community (EC) Number: 208-334-0,215-862-5
• UNII: 31J3Q51T6L
• DSSTox Substance ID: DTXSID70878516
• Wikipedia: Dihydroquinine
• Wikidata: Q5276450
• Metabolomics Workbench ID: 154503
• ChEMBL ID: CHEMBL588934
• Mol file: 522-66-7.mol

Synonyms:dihydroquinidine;dihydroquinine;hydroquinidine;hydroquinidine dihydrochloride, (1beta,4beta,3S)-(+-)-isomer;hydroquinidine dihydrochloride, (3alpha,9S)-(+-)-isomer;hydroquinidine hydrochloride;hydroquinidine monosulfate;hydroquinidine monosulfate, (1beta,3alpha,4beta,8alpha,9R)-isomer;hydroquinidine monosulfate, (1beta,3alpha,4beta,9S)-isomer;hydroquinidine sulfate;hydroquinidine sulfate, (9S)-isomer;hydroquinidine, (+-)-isomer;hydroquinidine, (1beta, 3alpha,4beta,8alpha,9R)-isomer;hydroquinidine, (1beta,3alpha,4beta,9S)-isomer;hydroquinidine, (1beta,4beta,9S)-(+-)-isomer;hydroquinidine, (3alpha,9S)-(+-)-isomer;hydroquinidine, (8alpha,9R)-isomer;hydroquinidine, (8alpha,9S)-isomer;hydroquinidine, (9R)-isomer;hydroquinidine, (9S)-(+-)-isomer;hydroquinine;LCN 834;LCN-834;Lentoquine;Sérécor

Chemical Property of Dihydroquinine

Chemical Property:

• Vapor Pressure: 9.45E-11mmHg at 25°C
• Melting Point: 168-176 °C
• Refractive Index: 1.626
• Boiling Point: 498.4 °C at 760 mmHg
• PKA: 5.33(at 25℃)
• Flash Point: 255.2 °C
• PSA: 45.59000
• Density: 1.2 g/cm³
• LogP: 3.33510
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethanol (Sparingly), Methanol (Slightly)
• Water Solubility.: 99.99mg/L(20 oC)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 326.199428076
• Heavy Atom Count: 24
• Complexity: 432

Purity/Quality:

95% ^*data from raw suppliers

(-)-Dihydroquinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OC)O
• Recent ClinicalTrials: Hydroquinidine Versus Placebo in Patients With Brugada Syndrome
• Uses: (-)-Dihydroquinine, is a dihydro derivative of Quinine (Q694000), having antipyretic (fever-reducing), antimalarial, analgesic (painkilling), and anti-inflammatory properties.

Technology Process of Dihydroquinine

There total 35 articles about Dihydroquinine 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%

Quinine (130-95-0) → dihydroquinine (522-66-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; for 3h; under 2280.15 Torr; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01962

Reference yield: 87.0%

2-(4-(tert-butyl)phenyl)benzo[d][1,3,2]dioxaborole (241147-96-6) + Quinine (130-95-0) → para-tert-butylphenol (98-54-4) + dihydroquinine (522-66-7)

Guidance literature:

With oxygen; hydrazine hydrate; In acetonitrile; at 32 ℃; for 4h; under 760.051 Torr; Schlenk technique;

DOI:10.1002/ejoc.201501222

Reference yield:

→ dihydroquinine (522-66-7)

Guidance literature:

With nickel; Hydrogenation;

upstream raw materials:

quinine hydrochloride

diazomethane

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

dimethyl sulfate

Downstream raw materials:

(8S,9R)-6'-Methoxy-2'-phenyl-10,11-dihydro-cinchonan-9-ol

phenylglyoxylate de la (-)-10,11-dihydroquinine

Dihydroquinidine 4-vinylbenzoate

Dihydroquinine 4-vinylbenzoate

Refernces

• 1、 -. "Synthesis method of hydroquinine(anthraquinone-1,4-diyl)diether". Paragraph 0072; 0073; 0074; 0075; 0076. . Retrieved 2020/10/21.
• 2、 W?sińska-Ka?wa, Ma?gorzata,Giurg, Miros?aw,Boratyński, Przemys?aw J.,Skar?ewski, Jacek. "Expansion of the aromatic part of Cinchona alkaloids. Annulation of quinolines with phenoxazine motifs". . p. 308 - 315. Retrieved 2017/12/08.