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| CAS No.: | 118-10-5 |
|---|---|
| Name: | Cinchonine |
| Molecular Structure: | |
|
|
|
| Formula: | C19H22N2O |
| Molecular Weight: | 294.396 |
| Synonyms: | (S)-[(5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;Quinoline alkaloid;.alpha.-Quinidine;Prestwick_501;(9S)-Cinchonan-9-ol;(S)-[(4R,5S,7S)-5-ethenyl-1-azoniabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;[(5S,7R)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;D-Cinchonine;Cinchonan-9-ol, (9S)-;2-Quinuclidinemethanol, .alpha.-(5-vinyl-2-quinolyl)-;4-quinolyl(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol;(+)-Cinconine; |
| EINECS: | 204-234-6 |
| Density: | 1.2 g/cm3 |
| Melting Point: | 256-266 °C |
| Boiling Point: | 464.5 °C at 760 mmHg |
| Flash Point: | 234.7 °C |
| Solubility: | insoluble in water |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: |
Xn
|
| Risk Codes: | 20/21/22 |
| Safety: | 26-36-36/37 |
| PSA: | 36.36000 |
| LogP: | 3.10250 |

O-tosylcinchonine

A

(Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate

B

Cinchonin

| Conditions | Yield |
|---|---|
| With salicylic acid In ethylene glycol at 95℃; for 0.5h; Microwave irradiation; | A 60% B 15% C 15% |


methanesulfonic acid (quinolin-4-yl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methyl ester

A

Cinchonin

C

(1S,2R,3S,5S,6R)-2-(quinolin-4-yl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol

| Conditions | Yield |
|---|---|
| With water; tartaric acid at 100℃; Title compound not separated from byproducts; | A n/a B n/a C 48% D 1% |




| Conditions | Yield |
|---|---|
| at 60 - 70℃; |


| Conditions | Yield |
|---|---|
| at 150 - 160℃; im Rohr; isomer(ic) I; |


| Conditions | Yield |
|---|---|
| With dibutyltin(II) dilaurate In toluene at 110℃; for 48h; | 99% |

| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -10 - 50℃; for 6h; Inert atmosphere; Schlenk technique; | 99% |
| In tetrahydrofuran at -78.16℃; for 12h; Inert atmosphere; |

anthracenylmethyl chloride


Cinchonin

| Conditions | Yield |
|---|---|
| In toluene at 110℃; for 2h; | 98% |
| In toluene Reflux; | 94% |
| In toluene for 24h; Heating; | 80% |

| Conditions | Yield |
|---|---|
| In tetrahydrofuran; N,N-dimethyl-formamide Reflux; | 98% |

| 1. | ipr-rat LD50:152 mg/kg | APTOA6 Acta Pharmacologica et Toxicologica. 4 (1948),265. | ||
| 2. | scu-mus LDLo:400 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 205 (1948),129. | ||
| 3. | scu-frg LDLo:200 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 205 (1948),129. |