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CAS No. : | 50777-76-9 | MDL No. : | MFCD00013367 |
Formula : | C19H15OP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DRCPJRZHAJMWOU-UHFFFAOYSA-N |
M.W : | 290.30 | Pubchem ID : | 2754316 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 90.54 |
TPSA : | 30.66 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.18 cm/s |
Log Po/w (iLOGP) : | 3.05 |
Log Po/w (XLOGP3) : | 4.07 |
Log Po/w (WLOGP) : | 3.26 |
Log Po/w (MLOGP) : | 4.25 |
Log Po/w (SILICOS-IT) : | 5.66 |
Consensus Log Po/w : | 4.06 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.57 |
Solubility : | 0.00774 mg/ml ; 0.0000267 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.42 |
Solubility : | 0.0111 mg/ml ; 0.0000382 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -7.48 |
Solubility : | 0.00000955 mg/ml ; 0.0000000329 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.64 |
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 |
---|---|---|
98% | With zirconium dioxide hydrate; isopropyl alcohol at 60℃; for 0.25h; | |
87% | With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In ethanol; acetonitrile at 60℃; for 24h; Autoclave; Glovebox; chemoselective reaction; | |
With sodium tetrahydroborate |
With sodium tetrahydroborate | ||
With sodium tetrahydroborate | ||
Multi-step reaction with 2 steps 1.1: dihydrogen peroxide / dichloromethane; water / 3 h / 20 °C / Glovebox; Inert atmosphere 2.1: trityl tetrakis(pentafluorophenyl)borate / (2)H8-toluene / 20 °C / Glovebox; Inert atmosphere 2.2: 80 °C / Glovebox; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In ethanol; water monomer for 2h; Ambient temperature; | |
70% | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In ethanol; water monomer for 3h; Schlenk technique; Inert atmosphere; Reflux; | |
2.6 g | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In methanol; water monomer for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In tetrahydrofuran;Reflux; Inert atmosphere; Schlenk technique; | General procedure: 2-(phosphino)benzaldehyde, (1) (2,0mmol) and (S)-(+)-isoleucinol (2,2mmol) was dissolved in 20mL THF and refluxed overnight. The reaction was monitored by 1H NMR and at the end of the reaction the volatiles were removed under reduced pressure. Degassed water (10mL) and dichloromethane (50mL) were added to the remained oily product. The organic layer separated, dried under Na2SO4 and evaporated to dryness. The imines (2) were obtained as pale-yellow oil. After the spectroscopic characterization, iminophosphines (2) (0.600g, 1.5mmol) were dissolved in methanol (30mL) and NaBH4 (0.150g, 4.0mmol) was added in three portion at room temperature. The reactions were monitored by 1H NMR and at the end of the reaction the volatiles were removed under reduced pressure. Degassed water (20mL) and dichloromethane (70mL) were added. The dichloromethane phases were washed with water (20ml), brine (20mL) and dried over Na2SO4. Spectroscopically pure oily products were obtained after the removing of the volatiles under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In dichloromethane for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With triethylamine In dichloromethane for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.9% | With hydrogenchloride In ethanol for 0.75h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: (2-bromophenyl)diphenylphosphane With n-butyllithium In diethyl ether; hexane at -78℃; for 0.333333h; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -78 - 20℃; Further stages.; | |
Stage #1: (2-bromophenyl)diphenylphosphane Stage #2: N,N-dimethyl-formamide Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol 2: 1.71 g / NaBH4 / ethanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Na2SO4 / CH2Cl2 / 24 h 2: NaBH4 / ethanol / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / Na2SO4 / CH2Cl2 / 24 h 2: 80 percent / NaBH4 / ethanol / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) fuming hydrochloric acid, 2.) H2O / 1.) reflux, 4 h, 2.) RT, 30 min 2: 75 percent / HSiCl3 / acetonitrile / 72 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of 2-diphenylphosphanylbenzaldehyde: After 5.9 ml of triethylamine (43 mmol) and 334 mg of tetrakis(triphenylphosphine)palladium have been added, 5 ml of 2-bromobenzaldehyde (43 mmol) and 11.15 ml of diphenylphosphine (64.5 mmol) are refluxed in 150 ml of absolute toluene under a protective gas atmosphere in a three-necked flask equipped with a reflux condenser. Triethylamine hydrobromide precipitates as a white solid over the course of the reaction. After 12 hours, the reaction solution is filtered, washed three times with saturated ammonium hydrochloride solution and saturated sodium chloride solution and the solvent is removed in a rotary evaporator. The resultant crude product is recrystallized from methanol. Yield 10.61 g (85% of theoretical). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In ethanol; dichloromethane; acetone | Preparation of (1 R,2R)-N-(2-diphenylphosphanylbenzyl)cyclohexane-1,2-diamine: Preparation of (1 R,2R)-N-(2-diphenylphosphanylbenzyl)cyclohexane-1,2-diamine: A solution, heated to 45° C., of 2.5 g of 2-diphenylphosphanylbenzaldehyde (8.6 mmol) in 250 ml of absolute ethanol is added dropwise over a period of 16 hours to a solution of 3.3 g of (1R,2R)-cyclohexane-1,2-diamine (28 mmol) in 500 ml of absolute ethanol at 0° C. under a protective gas atmosphere. The reaction solution is stirred for one hour at 0° C. and 1.37 g of sodium hydridoborate (36 mmol) are then added. The reaction mixture is slowly allowed to rise to room temperature and stirred for a further 12 hours. The reaction is then quenched by adding 100 ml of acetone and the solvent is completely removed in a rotary evaporator. The resultant residue is completely dissolved by adding 100 ml of saturated ammonium hydrochloride solution and 100 ml of methylene chloride. The organic phase is then separated and washed three times with water. 100 ml of 10% hydrochloric acid are then poured on and the mixture shaken. After a short time in the refrigerator, the product crystallises out as a white mass (hydrochloride). After drying under a high vacuum, a yield of 2.54 g (70% of theoretical) is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In benzene under N2; 4,4'-Ph2-2,2'-bipyridine (2 equiv.) added to benzene soln. of Rh complex; Ph2C6H4CHO (2 equiv.) added; stirred at room temp. for 1 h; filtered; solid washed with benzene; vac. dried; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In toluene at 20℃; for 1h; | [CuI(2-(diphenylphosphino)benzaldehyde)2] (1) A solution of CuI (0.2 g, 1.05 mmol) in toluene (50 ml) was mixed with 2-(diphenylphosphino) benzaldehyde (0.15 g, 0.52 mmol) also dissolved in toluene (20 ml). The solution is stirred for 1 hour at room temperature. After this time, a yellow precipitate is produced which is collected and dissolved in dichloromethane. After three days, single crystals suitable for X-ray diffraction were obtained by slow evaporation of the dichloromethane. Yield (82%) |
17% | In acetonitrile Cu-compd. was stirred in MeCN at 50 °C until a clear soln. was formed, 2 equiv. of P-compd. was added in MeCN, stirirng at 50 °C for 2 h; soln. was filtered and left at ambient temp. to evaporate for several days, solid was filtered off, dried in vac., elem. anal.; | |
In acetonitrile Cu-compd. was stirred in MeCN at 50 °C until a clear soln. was formed, 1 equiv. of P-compd. was added in MeCN, stirirng at 50 °C for 2 h; soln. was filtered and left at ambient temp. to evaporate for several days, solid was filtered off, dried in vac., elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In toluene at 150 - 160℃; for 6h; Inert atmosphere; | 8 General procedure for the synthesis of iminophosphine ligands (4-12).Procedure A General procedure: The iminophosphine ligands were prepared according to the method reported by Shirakawa and co-workers [70]. To 2-(diphenylphosphino)enzaldehyde(1) (200 mg, 0.689 mmol) 0.758 mmol (1.1 M equivalent) of the corresponding amine and 10 mL of freshly distilled toluene were added. The mixture was stirred under reflux (150-160 °C oil bath temperature) for 6 h.The solvent was removed in vacuo and the crude product was purified by bulb-to-bulb vacuum distillation (170 °C at 0.05 mm Hg,consistently used for all products) using a Kugel Rohr apparatus into which argon was continuously piped to prevent the ingress of oxygen. Since the iminophosphine products were unstable onsilica, no Rf-values are included for the iminophosphine ligands. |
92% | In dichloromethane at 20℃; for 16h; Inert atmosphere; | 4.2. General procedure for preparation of ligands (1a-f) General procedure: To a dichloromethane solution (15 mL) of 2-diphenylphosphinobenzaldehyde (ca. 3 mmol) was added an equimolar amount of the appropriate substituted amine. An excess of magnesium sulphate was also added to the reaction mixture to remove the water by-product. The reaction was left to stir at room temperature for 16 h, after which time the magnesium sulphate was filtered off and the solvent removed from the filtrate in vacuo to give a yellowe orange oil. The oily crude products of ligands 1a-1f were solidified by dissolving the oil in hot hexane, followed by quick hot filtration of the liquid product. The resultant solution was then cooled at -16 °C overnight to give an off-white powder, which was filtered and dried in vacuo. |
90% | With magnesium sulfate In dichloromethane at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: (2-bromophenyl)diphenylphosphane With n-butyllithium In diethyl ether; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2-formylphenyl)(diphenyl)phosphine In diethyl ether; hexane at 0℃; for 1.16667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With hydrogenchloride In ethanol at 56℃; for 1h; | 1.1 2.1.1 Synthesis of ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate (1) A mixture of 0.14 g (0.48 mmol) 2-(diphenylphosphino)benzaldehyde and 0.05 g (0.48 mmol) ethyl carbazate was dissolved, by heating, in 25 mL ethanol. pH of the mixture was adjusted to ∼4 with a hydrochloric acid. The mixture was heated at 56 °C for 60 min. The reaction solution was left to stand at room temperature while the colourless crystals separated from the solution. Yield 0.15 g (83%). Mp 164-166 °C. IR (vs-very strong, s-strong, m-medium, w-weak): 3253 (w), 3189 (w), 3049 (m), 2974 (w), 1729 (m), 1707 (s), 1550 (s), 1458 (w), 1435 (w), 1385 (w), 1247 (vs), 1178 (w), 1092 (w), 1055 (m), 763 (w), 744 (w), 696 (m), 657 (w), 499 (w). HRMS (ESI) of C22H21N2O2P found for (M+H+) 377.1384, calcd (m/z) for (M+H+) 377.1414. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: dichloromethane; diethyl ether / -48 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: toluene; hexane / -78 - 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: dichloromethane; diethyl ether / -48 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: toluene; hexane / -78 - 0 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: dichloromethane; diethyl ether / 4 h / -48 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: dichloromethane; diethyl ether / -48 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: titanium(IV)isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: toluene; hexane / -78 - 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide Heating; | Preparation and crystallization of compounds Preparation and crystallization of compounds;The ligands Ph2(Ph-CHO)P and Ph3P were obtained commercially. [Ph2(Ph-CHO)PAuX] for Cl, Br and I and [Ph3PAuBr] were prepared by dissolution of equimolar quantities of [NBu4][AuX2] and the phosphine ligand in warm dimethylformamide to give clear solutions from which slow evaporation of solvent yielded colorless air-stable crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide Heating; | Preparation and crystallization of compounds;The ligands Ph2(Ph-CHO)P and Ph3P were obtained commercially. [Ph2(Ph-CHO)PAuX] for Cl, Br and I and [Ph3PAuBr] were prepared by dissolution of equimolar quantities of [NBu4][AuX2] and the phosphine ligand in warm dimethylformamide to give clear solutions from which slow evaporation of solvent yielded colorless air-stable crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With sodium sulfate In dichloromethane for 24h; Inert atmosphere; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With sodium sulfate In dichloromethane for 24h; Inert atmosphere; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium sulfate In dichloromethane for 24h; Inert atmosphere; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium sulfate / dichloromethane / 24 h / Inert atmosphere; Glovebox; Schlenk technique 2: sodium tetrahydroborate / ethanol / 24 h / Inert atmosphere; Glovebox; Schlenk technique; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With acetic acid In ethanol for 1h; Reflux; | 2.4 Synthesis of PNS type thiosemicarbazone ligands General procedure: To a solution of 2-(diphenylphosphino)benzaldehyde (0.290g, 1mmol) and 4-ethyl-3-thiosemicarbazide (0.119g, 1mmol)/4-cyclohexyl-3-thiosemicarbazide (0.173g, 1mmol) in ethanol (20mL) were added 2-3 drops of glacial acetic acid. The resulting solution was heated under reflux over a 1h period, then concentrated to ca. 3mL and cooled to 0°C for overnight. The pale yellow precipitate was filtered off, washed with diethyl ether (2 x 5mL) and dried under vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With hydrogenchloride; In ethanol; water; for 1h;Reflux; | A mixture of 140 mg (0.48 mM) 2-(diphenylphosphino)benzaldehyde and 80 mg (0.48 mM) Girard?s T reagent was dissolved, by heating, in 20 mL ethanol and one drop of concentrated hydrochloric acid was added. The mixture was refluxed for 60 min. The reaction solution was left to stand at room temperature while the colorless crystals separated from the solution. Yield: 110 mg (47%); Mp 216 C. IR (vs-very strong, s-strong, m-medium, w-weak): 3524 (w), 3403 (w), 3308 (w), 3050 (m), 3018 (m), 2970 (m), 2930 (m), 2890 (m), 2817 (w), 1686 (vs), 1657 (m), 1602 (w), 1491 (w), 1475 (s), 1433 (s), 1410 (s), 1342 (w), 1306 (s), 1277 (w), 1212 (w), 1133 (w), 1123 (m), 1095 (w), 1044 (w), 992 (w), 948 (w), 929 (w), 876 (w), 848 (w), 765 (w), 746 (vs), 699 (s), 620 (w), 585 (w), 505 (w), 481 (w), 437 (w). Anal. Calcd for C24H27ClN3O2P*EtOH (%): N, 8.65; C, 64.26; H, 6.84.Found: N, 8.78; C, 64.17; H, 6.92. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 20 °C / Schlenk technique; Inert atmosphere 2.2: 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: titanium(IV) isopropylate / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 2: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane / 25 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: titanium(IV) isopropylate / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 2: tetrahydrofuran / 20 °C / Inert atmosphere |
Multi-step reaction with 2 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 4 h / 55 °C 2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / 1.5 h / -78 - 20 °C / Schlenk technique 2.2: Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium In ethanol at 60℃; for 2h; | 2.2.1. Preparation of fluorenylidine methyl phenyl diphenylphosphine (fmp(Ph)2P) Fluorene (16.62 g, 0.1 mol) was added to a solution of (3.9 g, 0.17 mol) sodium in 200-mL ethanol, the mixture was kept at 60 °C then a solution of (29 g, 0.1 mol) 2-diphenylphosphino benzaldehyde in 40-mLethanol was added dropwise. The mixture turned red after 2 h then the reaction was cooled and the solids were crystallized from dichloromethane-hexane. Yield: 85%, m.p.:153 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tert.-butyl lithium In toluene at 135℃; for 20h; Schlenk technique; Glovebox; Molecular sieve; | 2.3 Synthesis of Ligand 7 2-(Diphenylphosphino)benzaldehyde (2.09 g, 7.20 mmol, 1.0 equiv.) and mesitylamine (1.01 g,7.44 mmol, 1.03 mmol) were dissolved in 40 mL toluene. The orange solution was heated to 135 for 20 h under a dropping funnel filled with molecular sieves. Evaporating the solvent in vacuo yielded the product as a yellow solid, which was used in following syntheses without further purication (2.60 g, 6.38 mmol, 89 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In toluene; for 5h; | The synthesis of the iminophosphine ligand carryingalkoxylsilane moiety (A) was performed through the reactivedistillation of 2-(diphenylphosphino)benzaldehyde (0.500 g)with 3-(aminopropyl)trimethoxysilane (0.255 g) in dry toluene(25 mL). After 5 hours, we obtained a yellow oily liquidby careful removal of toluene under vacuum (87 % yield).1H NMR (400 MHz, CD2Cl2): delta = 8.8 (s, 1H), 8.02 (s,1H), 7.45-7.27 (m, 12 H), 6.91 (s, 1 H), 3.53 (s, 9 H), 3.46(m, 2 H), 1.68 - 1.60 (m, 2 H), 0.58 - 0.52 (m, 2 H); 13CNMR (100 MHz, CD2Cl2): delta= 158.57, 134.14, 128.79, 65.13,50.82, 24.62, 8.73 ppm.; 31P NMR : (300 MHz, CD2Cl2,ppm) delta= -13.07ppm. |
85% | In toluene; for 5h;Inert atmosphere; | The synthesis of the iminophosphine ligand carryingalkoxylsilane moiety A was performed through the reactive distillation of 2-(diphenylphosphino)benzaldehyde(0.500 g) with 3-(aminopropyl)trimethoxysilane (0.250 g)in dry toluene (25 mL). After 5 h, we obtained a yellowoily liquid by careful removal of toluene under vacuum(85 % yield).1H NMR (400 MHz, CD2Cl2): d = 8.8 (s, 1H), 8.02 (s,1H), 7.45-7.27 (m, 12 H), 6.91 (s, 1 H), 3.53 (s, 9 H), 3.46(m, 2 H), 1.68-1.60 (m, 2 H), 0.58-0.52 (m, 2 H); 13CNMR (100 MHz, CD2Cl2): d = 158.57, 134.14, 128.79,65.13, 50.82, 24.62, 8.73 ppm; 31P NMR: (300 MHz,CD2Cl2, ppm) d = -13.07 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With formic acid In ethanol for 2.5h; Reflux; | |
80% | In methanol for 2.5h; Inert atmosphere; Schlenk technique; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With caesium carbonate; In benzene; at 80℃; for 24h;Inert atmosphere; Schlenk technique; | Under inert gas protection,50 mL of Schlenk reaction tube was added<strong>[4733-39-5]2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolin</strong>e (0.180 g, 0.5 mmol)2- (diphenylphosphino) benzaldehyde (0.291 g, 1 mmol) andCesium carbonate (10 mmol),Addition of deoxygenated benzene (20 mL)Rose to 80 reaction 24h,Cooled to room temperature, 50 mL of water was added to the reaction solution, the solid was precipitated and filtered,The filtered solid was recrystallized from 10 mL of crystalline solvent ethanol,To give 384 mg of the desired product, 85% yield, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With acetic acid In ethanol for 3h; Reflux; | 2.2 Synthesis of 2-(2-(diphenylphosphino)benzylidene)-2-thiophenecarboxylic acid hydrazone (PNO-THy) ligand To a solution of 2-(diphenylphosphino)benzaldehyde (0.290g, 1mmol) and 2-thiophene carboxylic acid hydrazide (0.126g, 1mmol) in ethanol (20mL) were added 2-3 drops of glacial acetic acid. The resulting solution was heated under reflux over a 3h period, and then concentrated to ca. 3mL. The white crystalline precipitate was filtered off, washed with diethyl ether (2×5mL), and dried under vacuo. Yield: 87% (0.36g). Mp: 197-199°C. Anal. Calcd for C24H19N2OPS: C, 69.55; H, 4.62; N, 6.76; S, 7.74. Found: C, 69.67; H, 4.58; N, 6.86; S, 7.69. IR (KBr disks, cm-1): 3195 (m, νNH); 1685 (s, νC=O); 1583+1474 (s, νC=N+νC-N). 1H NMR (400MHz, DMSO-d6, ppm): 6.83-7.50 (m, 14H, Ar H), 7.57 (t, 1H, J=6.24, Hz Ar H), 8.05 (s, 1H, Ar H), 8.15 (s, 1H, Ar H), 8.85 (d, IH, J=3.6Hz, -CH=N), 9.13 (s, 1H, Ar H), 11.98 (s, IH, -NH). 13C NMR (100MHz, DMSO-d6, ppm): 125.78 (Ar C), 128.91 (Ar C), 129.15 (Ar C), 129.47 (Ar C), 130.07 (Ar C), 133.30 (Ar C), 133.49 (Ar C), 134.12 (Ar C), 135.62 (Ar C), 138.25 (Ar C), 149.52 (-CH=N), 158.12 (C=O). 31P NMR (162MHz, DMSO-d6, ppm): -17.14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: titanium(IV) isopropylate / tetrahydrofuran / 4 h / 50 °C / Inert atmosphere 2.1: tetrahydrofuran / 20 °C / Inert atmosphere 3.1: borane-THF / 20 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With trimethylamine-N-oxide; C27H28FeN3O3(1+)*BF4(1-); hydrogen In ethanol at 20℃; for 16h; Autoclave; Inert atmosphere; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: (2-formylphenyl)(diphenyl)phosphine; (2S)-2-[(diphenylphosphino)methyl]pyrrolidine In methanol Inert atmosphere; Reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; Inert atmosphere; | 4 Example 4 Preparation of (L)-N-[(2-diphenylphosphinophenyl)methyl]-2-[(diphenylphosphino)methyl]pyrrolidine Under the protection of nitrogen, 2-diphenylphosphine benzaldehyde (13.52mmol, 3.92g) was added to the double-necked flask equipped with a reflux condenser.(L)-2-[(diphenylphosphine)methyl]pyrrolidine (12.29mmol, 3.31g), methanol 10mL, refluxed overnight, added sodium borohydride (24.58mmol, 0.93g) in three batches ,Cool the round-bottom flask to room temperature, desolvate, and prepare by fast liquid chromatography (ethyl acetate: petroleum ether volume ratio of 1%-5%) after purification0.96 g, 67% of colorless transparent oily liquid was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: (R)-7′-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spiroindene; (2-formylphenyl)(diphenyl)phosphine With acetic acid In methanol at 20℃; for 3h; Inert atmosphere; Schlenk technique; Stage #2: With sodium cyanoborohydride In methanol at 40℃; for 15h; Inert atmosphere; | 1 Example 1:Synthetic route of ligand Ia In an argon atmosphere, weigh (R)-7′-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spiroindene 4a (300mg, 0.46mmol) in a 100mL dry Schlenk tube,Inject 12 mL of anhydrous methanol into the syringe and stir to dissolve. Add 2-diphenylphosphine benzaldehyde (176 mg, 0.61 mmol) and glacial acetic acid (42 μL). The reaction was stirred at room temperature for 3 hours.Open the anti-port plug and pour NaBH3CN (87mg, 1.38mmol) in one go,The reaction was carried out at 40 degrees for 15 hours. After the reaction, it was cooled to room temperature, and the system was spin-dried.Add dichloromethane to dissolve and quench with saturated sodium bicarbonate solution. Dichloromethane extraction,Combine the organic phases, dry the organic phases with anhydrous magnesium sulfate, and remove the desiccant by suction filtration.The filtrate was used to remove the solvent with a rotary evaporator.The residue was subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 30:1)342 mg of white solid Ia was obtained with a yield of 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With toluene-4-sulfonic acid In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With piperidine; acetic acid In toluene at 110℃; for 24h; Molecular sieve; Inert atmosphere; Green chemistry; stereoselective reaction; | Knoevenagel Condensation between 2-(Diphenylphosphino)benzaldehyde and Phosphinoylacetic Acids 2; General Procedure General procedure: The aldol reactions were carried out in a 15 mL vial. In a typical reaction, the vial was charged at r.t. with the reactants in the following order: the respective phosphinoylacetic acid 2 (0.76 mmol), aldehyde (0.95 mmol), toluene (6 mL), catalysts (Table 4), and molecular sieves (100 mg). The flask was purged with argon atmosphere, capped with a stopper, and sealed. Then, the reaction mixture was stirred at 110 °C for the 24 h. The mixture was filtered and concentrated under reduced pressure. The product conversion with respect to the phosphinoylacetic acids and E/Z ratio were determined by 31P NMR analysis in CDCl3 on the crude mixture. The crude residue was purified by column chromatography on silica gel (eluent: EtOAc/i-PrOH with a gradient mixture ratio from 90:10 to 70:30). (E)-[2-(Diphenylphosphine)styryl]diphenylphosphine Oxide (L1) According to the general procedure, the reaction of 2a (198 mg, 0.76 mmol) afforded product L1 as a white solid; yield: 338 mg (91%). 1H NMR (500 MHz, CDCl3): δ = 7.73 (ddd, J = 20.1, 17.2, 4.9 Hz, 1 H), 7.66-7.58 (m, 1 H), 7.52-7.43 (m, 6 H), 7.41-7.28 (m, 11 H), 7.23 (t, J =7.6 Hz, 1 H), 7.16 (td, J = 8.0, 1.5 Hz, 4 H), 6.81 (ddd, J = 7.8, 4.3, 1.3 Hz, 1 H), 6.64 (td, J = 17.1, 1.1 Hz, 1 H). 13C NMR (126 MHz, CDCl3): δ = 146.15 (dd, J = 24.7, 6.0 Hz), 140.10 (d, J = 18.4 Hz), 139.93 (d, J = 18.4 Hz), 137.33 (d, J = 16.4 Hz), 135.69 (d, J = 10.3 Hz), 134.15 (d, J = 20.0 Hz), 133.05, 131.95 (d, J = 100.8 Hz), 131.75 (d, J = 2.7 Hz), 131.58 (d, J = 10.0 Hz), 129.63, 129.13, 129.01, 128.67 (d, J = 7.2 Hz), 128.50 (d, J = 12.2 Hz), 126.81 (d, J = 3.3 Hz), 122.88 (dd, J = 103.5, 3.4 Hz). 31P NMR (202 MHz, CDCl3): δ = 26.41, -13.82. LCMS: m/z [M + H]+ calcd for C32H27O2P2+: 505.1481; found: 505.1486. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With sodium dithionite In ethanol; water at 75℃; for 5h; | |
43% | With sodium dithionite In ethanol; water at 75℃; for 5h; | |
43% | With sodium dithionite In ethanol; water for 5h; Reflux; | Synthesis of HL1 General procedure: The 2-nitroaniline (0.71g, 5mmol), 2-(diphenylphosphino)benzaldehyde (1.74g, 6mmol) and sodium hydrosulfite (3.48g, 20mmol) in a mixture of the ethanol and water (v/v=5:1) were refluxed for 5h. The reaction mixture was filtered to remove the precipitated base. Then, the filtrate was concentrated under reduced pressure to remove the mixture of ethanol and water, and then extracted with ethyl acetate. The crude product was purified by silica gel column chromatography using dichloromethane/ethyl acetate (10:1) as the eluent to afford HL1 as a white solid (0.93g, 47% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium(IV) isopropylate / tetrahydrofuran / 50 °C 2: dichloromethane; diethyl ether / -48 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol at 20℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium isopropoxide / tetrahydrofuran / 50 °C / Inert atmosphere 2: tetrahydrofuran / -48 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: chromium(0) hexacarbonyl / 15 h / 120 °C / Inert atmosphere 2: hydrogenchloride / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: (1R,2R)-1,2-diphenyl-2-(piperidin-1-yl)ethan-1-amine; (2-formylphenyl)(diphenyl)phosphine In methanol at 80℃; for 1h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydridoborate at 80℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: C18H22N2; (2-formylphenyl)(diphenyl)phosphine In methanol at 80℃; for 1h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydridoborate at 80℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: (1S,2S)-1,2-diphenyl-2-(piperidin-1-yl)ethan-1-amine; (2-formylphenyl)(diphenyl)phosphine In methanol at 80℃; for 1h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydridoborate at 80℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89 % | With potassium <i>tert</i>-butylate; 1-amino-1,4-diazabicyclo[2.2.2]octane-1,4-diium iodide In tetrahydrofuran at 20℃; | 32 Example 32 Add H2N-DABCO (0.25mmol, 95.7mg), tBuOK (0.5mmol, 56.4mg) and 2mL THF in a vial, stir for 5min, then add 2-diphenylphosphinebenzaldehyde (0.25mmol, 72.6mg), stir for 2-5min. After the reaction was completed, saturated aqueous sodium bicarbonate solution and ethyl acetate (3×10 mL) were added to the system for extraction, and the product was separated by column chromatography with a yield of 89%. |
Tags: 50777-76-9 synthesis path| 50777-76-9 SDS| 50777-76-9 COA| 50777-76-9 purity| 50777-76-9 application| 50777-76-9 NMR| 50777-76-9 COA| 50777-76-9 structure
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