485-65-4

Basic information

• Product Name: HYDROCINCHONINE
• Synonyms: HYDROCINCHONINE;DIHYDROCINCHONINE;(9S)-10,11-dihydrocinchonan-9-ol;HYDROCINCHONINE 97%;Cinconifine;(1S)-((2R,4S,5R)-5-Ethylquinuclidin-2-yl)(quinolin-4-yl)methanol;(S)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(quinolin-4-yl)methanol
• CAS NO: 485-65-4
• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.41
• EINECS: 207-621-8
• Product Categories: 18031153937@189.cn;4clpvp ada@tuskwei.com sky
• Mol File: 485-65-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 269-272 °C(lit.)
• Boiling Point: 438°C (rough estimate)
• Flash Point: 236.309 °C
• Appearance: /
• Density: 1.0689 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• PKA: 12.98±0.20(Predicted)
• Water Solubility: 768.6mg/L(25 oC)
• Merck: 13,4804
• BRN: 4296749
• CAS DataBase Reference: HYDROCINCHONINE(CAS DataBase Reference)
• NIST Chemistry Reference: HYDROCINCHONINE(485-65-4)
• EPA Substance Registry System: HYDROCINCHONINE(485-65-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 485-65-4(Hazardous Substances Data)

Usage

Uses

Hydrocinchonin is used in the enantioselective hydrogenation of α-ketoesters and the enantioselective synthesis of functionalized α-aminophosphonic acid derivatives.

InChI:InChI=1/C19H24N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3/t13-,14-,18+,19-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 34304-08-0 10,11-dihydro-cinchonan-9-one 
• 141-52-6 sodium ethanolate 
• 7647-01-0 hydrogenchloride 
• 91021-95-3 (9S)-9-Sulfooxy-10,11-dihydro-cinchonan 
• 118-10-5 cinchonine 
• 4363-93-3 quinoline-4-carboxaldehyde 
• 109922-58-9 (4S,5R,6S)-5-Ethyl-4-((E)-3-quinolin-4-yl-allyl)-6-((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester 
• 109922-60-3 4-[(E)-3-((3R,4R)-3-Ethyl-piperidin-4-yl)-propenyl]-quinoline 
• 109922-57-8 [4]quinolyl-acetic acid 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 109922-61-4 1-[(3R,4S)-3-Ethyl-4-(3-quinolin-4-yl-oxiranylmethyl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone 
• 73522-75-5 4-((S)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(hydroxy)methyl)quinolin-6-ol 
• 118-10-5 Cinchonin 

Downstream Products

• 35167-97-6 [(4S)-cis-(3-ethyl-[4]piperidyl)-acetic acid 
• 486-74-8 4-quinolinic acid 
• 73522-74-4 hydrocinchonine 
• 485-64-3 (-)-hydrocinchonidine 
• 73522-73-3 hydrocinchonidine 
• 1092380-81-8 C₂₆H₃₀N₂O 
• 1261665-85-3 N-(3-trifluoromethylbenzyl)dihydrocinchoninium bromide 

Relevant articles and documents

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Enantioselective photooxygenation of β-dicarbonyl compounds in batch and flow photomicroreactors

A series of C-2′ modified cinchonine-derived phase-transfer catalysts were synthesized and used in the enantioselective photo-organocatalytic aerobic oxidation of β-dicarbonyl compounds with excellent yields (up to 97%) and high enantioselectivities (up to 90% ee). Furthermore, the reaction was carried out in a flow photomicroreactor, in which the heterogeneous gas-liquid-liquid asymmetric photocatalytic oxidation reaction was performed affording good yields (up to 97%) and enantioselectivities (up to 86% ee) within 0.89 min.

Asymmetric direct α-hydroxylation of β-Oxo esters by phase-transfer catalysis using chiral quaternary ammonium salts

The first enantioselective direct α-hydroxylation of β-oxo esters was developed by using phase-transfer catalysis. 1-Indanone-derived 1-adamantyl (1-Ad) β-oxo esters, in the presence of commercially available cumyl hydroperoxide and a cinchonine-based ammonium salt, resulted in the corresponding products with 69-91 % yield and 65-74 % ee. The reaction had also been successfully scaled-up to a gram quantity, and a similar yield was obtained without loss of the enantioselectivity. Copyright

Highly enantioselective radical addition to N-benzoyl hydrazones using chiral ammonium salts

In the presence of a protonated cinchonine derivative, radical addition reactions proceeded efficiently, affording addition adducts in high yields with an extremely high enantioselectivity. The chiral ammonium salt was recyclable after a simple aqueous workup. The reaction provides environmentally benign reaction conditions. Copyright