(1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol

Base Information

• Chemical Name: (1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol
• CAS No.: 118-10-5
• Deprecated CAS: 1236363-47-5,185122-83-2,201406-15-7,24831-03-6,887770-70-9,896440-46-3,898337-50-3,898814-05-6,900786-85-8,909881-46-5,910892-13-6
• Molecular Formula: C19H22N2O
• Molecular Weight: 294.396
• Hs Code.: 29339900
• European Community (EC) Number: 204-234-6
• Nikkaji Number: J1.503.306A
• Wikipedia: Cinchonine
• Mol file: 118-10-5.mol

Synonyms:MLS006011995;NP89;SCHEMBL18950292;118-10-5;AKOS030504193;SMR004703548;(1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol

Chemical Property of (1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 256-266 °C
• Refractive Index: 223 ° (C=0.5, EtOH)
• Boiling Point: 464.5 °C at 760 mmHg
• PKA: 5.85, 9.92(at 25℃)
• Flash Point: 234.7 °C
• PSA: 36.36000
• Density: 1.2 g/cm³
• LogP: 3.10250
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 0.25g/l
• Water Solubility.: Insoluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 294.173213330
• Heavy Atom Count: 22
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

Cinchonine >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-20/21/22
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
• Isomeric SMILES: C=C[C@H]1CN2CCC1CC2[C@@H](C3=CC=NC4=CC=CC=C34)O
• Description: Cinchonine is a cinchona alkaloid generally found in the bark of Cinchona officinalis plants. It is a pseudoenantiomer that is commonly employed in malaria therapy. Cinchonine is also used as an organocatalyst in many asymmetric reactions. It is a stereoisomer and pseudo-enantiomer of cinchonidine. It is structurally similar to quinine, an antimalarial drug.
• Uses: cardiotonic Stereomeric with Cinchonidine (C441925). Antimalarial. Cinchonine occurs in most varieties of cinchonabark (Cinchona micrantha and Rubiaceae).It is used as an antimalarial agent.

Technology Process of (1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol

There total 53 articles about (1R)((5R)-5-vinylquinuclidin-2-yl)-4-quinolylmethan-1-ol 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: 60.0%

O-tosylcinchonine (189309-24-8) → (Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate (1393446-38-2) + Cinchonin (118-10-5) + (+)-cinchonine (118-10-5,485-70-1,485-71-2,550-54-9,40134-63-2,72402-55-2,72402-56-3)

Guidance literature:

With salicylic acid; In ethylene glycol; at 95 ℃; for 0.5h; Microwave irradiation;

DOI:10.3998/ark.5550190.0013.625

Reference yield: 60.0%

O-tosylcinchonine (189309-24-8) → (Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate (1393446-38-2) + Cinchonin (118-10-5) + (+)-cinchonine (118-10-5,485-70-1,485-71-2,550-54-9,40134-63-2,72402-55-2,72402-56-3)

Guidance literature:

With salicylic acid; In ethylene glycol; at 95 ℃; for 0.5h; Microwave irradiation;

DOI:10.3998/ark.5550190.0013.625

Reference yield: 60.0%

O-tosylcinchonine (189309-24-8) → (Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate (1393446-38-2) + Cinchonin (118-10-5) + (+)-cinchonine (118-10-5,485-70-1,485-71-2,550-54-9,40134-63-2,72402-55-2,72402-56-3)

Guidance literature:

With salicylic acid; In ethylene glycol; at 95 ℃; for 0.5h; Microwave irradiation;

DOI:10.3998/ark.5550190.0013.625

upstream raw materials:

cinchonine

cinchonidine

O-tosylcinchonine

cinchonan-9-one

Downstream raw materials:

10,11-dihydrocinchonidine

C⁽⁹⁾-epi-cinchonidine

cinchonine-diphenylphosphinite

(4S,5R)-1,3-dibenzyl-5-formyl-2-oxo-4-imidazolidine carboxylic acid cinchonidine salt

Refernces

Heterocyclic amine salts of Keggin heteropolyacids used as catalyst for the selective oxidation of sulfides to sulfoxides

10.1016/j.tetlet.2008.01.009

The research focuses on the selective oxidation of sulfides to sulfoxides using heterocyclic amine salts of Keggin heteropolyacids as catalysts. The study explores the effectiveness of various heteropolyacids, including those derived from quinoline (PM12Qui), cinchonidine (PM12Cid), and cinchonine (PM12Cin), in combination with different green oxidants such as hydrogen peroxide, urea–hydrogen peroxide complex, sodium percarbonate, and tert-butyl-hydroperoxide. The experiments were conducted under various conditions to optimize the reaction yields and selectivity. Key findings include the high catalytic activity and recoverability of the cinchonine heteropolyacid catalyst, which also demonstrated enantioselectivity in the oxidation process. The study highlights the operational simplicity, mild reaction conditions, and high yields achieved, positioning these catalysts as a green alternative for the oxidation of sulfides to sulfoxides.