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CAS No. : | 33985-71-6 | MDL No. : | MFCD00151555 |
Formula : | C13H15NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XIIVBURSIWWDEO-UHFFFAOYSA-N |
M.W : | 201.26 | Pubchem ID : | 98700 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.46 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.29 |
TPSA : | 20.31 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.9 cm/s |
Log Po/w (iLOGP) : | 2.15 |
Log Po/w (XLOGP3) : | 2.29 |
Log Po/w (WLOGP) : | 1.82 |
Log Po/w (MLOGP) : | 2.19 |
Log Po/w (SILICOS-IT) : | 3.14 |
Consensus Log Po/w : | 2.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.76 |
Solubility : | 0.349 mg/ml ; 0.00174 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.35 |
Solubility : | 0.891 mg/ml ; 0.00443 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.35 |
Solubility : | 0.0905 mg/ml ; 0.00045 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.79 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With trichlorophosphate In dichloromethane at 20℃; for 4 h; Inert atmosphere | Julolidine (0.5 g, 2.89 mmol), DMF (0.255 g, 3.49 mmol)and POCl3 (0.535 g, 3.49 mmol) were dissolved in DCM(15 mL) and the mixture was stirred at room temperaturefor 4 h under an inert argon atmosphere. The solution’scolor turned green and the degree of advancement was followedby TLC. The solution was treated with aq. NaOH(2 M) and the crude product then was extracted withEt2O. After two aqueous washings, the organic phase wasdried on MgSO4, filtered and concentrated under vacuum.The product was then purified on column chromatographyusing 40percent–50percent Et2O: Hexane was used as the eluentto give 0.48 g (83.08percent) (the reaction yield was upto 92percent when 1.5 g julolidine was used as starting material)of a light yellow solid product.1H NMR (300 MHz,CDCl3: = 9597 (s, 1 H), 7.29 (s, 1 H), 3.308 (t, J =57 Hz, 4 H), 2.787 (t, J = 62, 4 H), 2.002–1.92 (m, J =63, 4 H). |
80% | Stage #1: at 0℃; Inert atmosphere Stage #2: at 0 - 20℃; Inert atmosphere |
2,3,6,7-Tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde was synthesized according to the described method [Kauffman, Joel M.; Imbesi, Steven J.; Aziz, Mohammed Abdul - Organic Preparations and Procedures International, 2001, vol. 33, 6, p. 603 - 613] with some modifications: to a magnetically stirred solution of POCl3 (2.2 ml, 23 mmol) in DMF (2 ml) julolidine (2) (2 g, 11.6 mmol) and DMF (2 mL) under argon was added dropwise at 0 °C. Then the mixture was allowed to stir for 3 h at rt (TLC). Ammonium hydroxide was added for neutralization and the solution was deluted with ethyl acetate and washed with water several times. The residue was purified by column chromatography (silica gel, 10percent ethyl acetate/hexane). Yield 1.8 g (80percent). 1H NMR (300 MHz, CDCl3): δ 9.63 (s, 1H), 7.28 (s, 2H), 3.31 (t, J=5.8 Hz, 4H), 2.81 (t, J= 6.2 Hz, 4H), 1.97–2.06 (m, 4H). |
71% | With trichlorophosphate In N,N-dimethyl-formamide at 90℃; for 4.5 h; | The synthesis of 9-formyljulolidinewas carried outmodifying a reported procedure [45,46]. In brief,phosphorous oxychloride (1.1 mL, 11.55 mmol) was added dropwise to N,N-dimethyl-formamide(2 mL, 25.85 mmol) at 0 °C. A solution of julolidine (2.0015 g, 11.55 mmol) in DMF (3.5 mL, 45.24 mmol)was then added and the mixture was stirred at 90 °C for 4.5 h. The solution was allowed to coolat room temperature (rt) and neutralized to pH 6–8 by the addition of a saturated sodium acetatesolution (~30 mL). After stirring overnight at rt, a greenish-yellow solid precipitate was recoveredvia filtration, washed with water (30 mL) and dried under high vacuum. The crude product waspurified through column chromatography on silica gel using ethyl acetate/CHCl3 (70/30 v/v) aseluent mixture. 1.65 g of FJUL were recovered (71percent yield). FT-IR (KBr, cm-1): 2758, 1651, 1594,1527, 1321. 1H-NMR (CDCl3): δ (ppm) = 9.6 (s, 1H, CHO), 7.3 (s, 2H, aromatic), 3.3 (t, J = 5.8 Hz,4H, NCH2), 2.7 (t, J = 6.3 Hz, 4H, NCH2CH2CH2), 1.9 (m, 4H, NCH2CH2). 13C-NMR (CDCl3): δ (ppm) = 190.1 (-CHO), 147.9 (-N-C(-C-)=C-), 129.5 (-C(=C)-CH=C(-C)-CH=), 124.0 (-CH-(CH=)C-CHO),120.33 (-CH2-C(=C-)-CH(=C)), 50.0 (-N(-CH2)-), 27.7 (-N(-CH2-CH2-CH2-)-), 21.3 (-N(-CH2-CH2-CH2-)-).EI-MS m/z (percent): 201 (100, M+). |
60% | With trichlorophosphate In dichloromethane at 25℃; for 8 h; | In brief, phosphorous oxychloride (0.29 mL, 3.17 mmol) was added dropwise to a solution of julolidine(0.5 g, 2.88 mmol) and N,N-dimethylformamide (0.27 mL,3.45 mmol) in anhydrous dichloromethane (5 mL) and the mixture was stirred for 8 h at 25 C. The reaction was treated with an aqueous solution of sodium hydroxide (2 M) and the mixture was stirred at 0 C for 4 h. The organic layer was extracted with diethyl ether, dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude product was purified by column chromatography on silica gel (230400 mesh) using diethyl ether/n-hexane (3/7 v/v) as eluent mixture (Rf 0.37) (60percent yield). FT-IR (KBr, cm1): 2950, 2895, 1662, 1600, 1320, 900, 720.1H NMR (CDCl3) (ppm): 9.6 (s, 1H, CHO), 7.3 (s, 2H, aromatic), 3.3(t, 4H NCH2), 2.7 (t, 4H NCH2CH2CH2), 1.9 (m, 4H NCH2CH2).13C NMR (CDCl3) (ppm): 191.3 (CHO), 149.1 (CeN aromatic),128.5 to 122.0 (aromatic), 49.3 (NCH2), 28.1 to 20.4 (NCH2CH2CH2). EI-MS m/z (percent): 201 (100, M). |
42.7% | at 80 - 100℃; for 2 h; Inert atmosphere; Cooling with ice | Dry N,N-dimethylformamide (DMF) (3.4 mL, 43.9 mmol) was charged into around bottom flask fitted with a magnetic stirrer and pressure-equalizing dropping funnel. The flask was purged withdry nitrogen and cooled in an ice bath. Phosphorus oxychloride (0.79 mL, 8.5 mmol) was then added slowly to the DMF. A solution of 2,3,6,7-tetrahydro-1H,5H-benzo-quinolizine(julolidine) (1.47 g, 8.5 mmol) in DMF (1.36 mL) was then added with vigorous stirring to the mixture and the resulting mixture was heated at 80-100 °C for 2 h. The solution was allowed to cool to room temperature and was poured into ice water. The solution was neutralized to pH 6-8 by addition of saturated sodium acetate. The desired aldehyde precipitated out of solution as a greenish-yellow solid. The solid was filtered, washed with water and hexane, and dried to obtain pure aldehyde 1 (0.731 g). Yield: 42.7percent. 1H NMR (500 MHz, CDCl3) δ 1.37 (p, 2x2H), 2.8 (t, 2x2H),3.3 (2x2H, t), 7.29 (2x1H, s), 9.6 (s, 1H, CHO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: at 0℃; for 1.25 h; Stage #2: for 1.16667 h; |
N,N-Dimethylformamide (21.4 g) was placed in a flask and stirred with cooling on an ice bath, and phosphorus oxychloride (13.3 g) was dropwise added over 15 minutes. The mixture was stirred at the same temperature for 1 hour, and a solution of julolidine (5.1 g) represented by the following (F-1) in N,N-dimethylformamide (10 ml) was dropwise added over 10 minutes. After 1 hour, a reaction mixture was poured into a diluted sodium hydroxide aqueous solution (200 ml), and an organic component was extracted with toluene. The solvent was distilled off, and a residue was purified by silica gel column chromatography, to give the following compound (F-2). 5.3 g. Yield 91 percent. |
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