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* Storage: {[proInfo.prStorage]}
CAS No. : | 53199-31-8 | MDL No. : | MFCD03094580 |
Formula : | C24H54P2Pd | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MXQOYLRVSVOCQT-UHFFFAOYSA-N |
M.W : | 511.05 | Pubchem ID : | 2734558 |
Synonyms : |
|
Chemical Name : | Bis(tri-tert-butylphosphine)palladium |
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 135.78 |
TPSA : | 27.18 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.31 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 5.78 |
Log Po/w (WLOGP) : | 9.73 |
Log Po/w (MLOGP) : | 7.33 |
Log Po/w (SILICOS-IT) : | 4.03 |
Consensus Log Po/w : | 5.37 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -6.25 |
Solubility : | 0.000285 mg/ml ; 0.000000557 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.12 |
Solubility : | 0.000388 mg/ml ; 0.000000759 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -3.63 |
Solubility : | 0.121 mg/ml ; 0.000236 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 5.48 |
Signal Word: | Danger | Class: | 4.1 |
Precautionary Statements: | P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | 1325 |
Hazard Statements: | H315-H319-H228 | Packing Group: | Ⅱ |
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 |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; hydrogenchloride; ethyl acetate; | Example 29 Preparation of 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44) This example describes the synthesis of common ligand mimics of the invention containing a linker group following the reaction scheme shown in . Compound numbers correspond to the numbers in the figure. The compounds 4-allyl-5-(4-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (compound 42, 500 mg, 2.28 mmol) and 5-(4-bromo-phenyl)-furfural were mixed in dioxane (10 ml), followed by the addition of diisopropylethylamine (0.795 ml, 4.56 mmol). Bis(tri-tert-butylphosphine) palladium (56 mg, 0.109 mmol) was added to the reaction mixture, which then was stirred at a temperature of 90 C. for a period of 1 hour. Volatiles were removed in vacuo, and the residue was diluted in 0.2 N HCl solution, followed by extraction with ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient 7:3 to 9:1 ethyl acetate/hexanes+0.5% MeOH) to give 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44, 375 mg, 42%). 1H NMR (300 MHz, CDCl3) delta 4.55 (d, J=4.7, 2H), 6.31 (td, J=3.2, 16.0, 1H), 6.44 (d, J=16.0, 1H), 6.84 (d, J=3.7, 1H), 7.18 (dd, J=8.5, JHF=8.5, 2H), 7.32 (d, J=3.7, 1H), 7.40 (d, J=8.3, 2H), 7.61 (dd, J=8.5, JHF=5.2, 2H), 7.76 (d, J=8.3, 2H), 9.64 (s, 1H), 10.56 (s, 1H); 13C NMR (300 MHz, CDCl3) delta 43.8, 107.9, 116.3 (d, JCF=22), 123.2, 124.4, 125.6, 127.1, 128.7, 130.3 (d, JCF=9), 132.3, 137.1, 147.0, 152.2, 155.7, 158.9, 164.1 (d, JCF=250), 206.6; MS m/s 389.96 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In n-heptane; ethyl acetate; toluene; | B. Synthesis of 3-(1-pyrrolidinyl)phenol 7g (30 mmol) of 1-Bromo-3-methoxymethoxy-benzene from step A and 2,5 g (35 mmol) of pyrrolidine were dissolved under argon in 60 mL of toluene. Then, 0.15 g (0.3 mmol) of <strong>[53199-31-8]bis(tri-t-butylphosphine)palladium(0)</strong>, 2,5g KOH und 0,6g (0,15 mmol) cetyltrimethylammoniumbromid were added, and the reaction mixture was heated at 80 C. At the end of the reaction, the reaction mixture was poured into 200 mL of ethyl acetate, and the organic phase was extracted with 1 N sodium hydroxide solution and then dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel using heptane/ethyl acetate (8/0,8). The product thus obtained was dissolved in 15 mL of ethanol and mixed with 10 mL of a 2.9 molar solution of ethanolic hydrochloric acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.88 g (21%) | zinc(II) chloride; In tetrahydrofuran; dichloromethane; water; pentane; | 3'-[(E)-[(2,6-Diisopropylphenyl)imino](phenyl)methyl]-2'-methoxy-5'-methylbiphenyl-2-ol (29): To a solution of 9.74 g (56.3 mmol) of 2-bromophenol in 200 mL of THF, 105 mL (169 mmol) of 1.6 M tBuLi in pentane was added dropwise with vigorous stirring for 40 min at -80 C. This mixture was stirred for 1 hr at this, then slowly warmed to room temperature, and stirred for 30 min. The resulting mixture was cooled to -80 C., and a solution of 15.3 g (112 mmol) of ZnCl2 in 110 mL of THF was added. The resulting mixture was slowly warmed to room temperature, stirred for 1 hr, and then evaporated to dryness. A mixture of the residue, 15.3 g (33 mmol) of N-[(1E/1Z)-(3-bromo-2-methoxy-5-methylphenyl)(phenyl)-methylene]-2,6-diisopropylaniline, 190 mg (0.37 mmol) of Pd(PtBu3)2 and 200 mL of THF was stirred for 12 hr at 85 C. 5 mL of water was The resulting mixture was evaporated to dryness. To the residue 150 mL of dichloromethane was added, and the obtained solution was passed through short layer of silica gel 60 (40-63 um). The silica gel layer was additionally washed by 2*200 mL of dichloromethane. The combined organic extract was evaporated to dryness. The product was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=10:1, vol.). Yield 1.88 g (21%) of the title product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium acetate; In water; | (E)-Ethyl 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylate Following the general procedure, using (E)-ethyl 3-(4-bromophenyl)acrylate (128 mg, 0.5 mmol), Pd(PtBu3)2 (7.7 mg, 0.015 mmol), B2pin2 (140 mg, 0.55 mmol), and KOAc (147 mg, 1.5 mmol) in 2 mL of 2% TPGS-750-M/H2O, GC/FID and TLC monitoring indicated complete conversion after an overall reaction time of 6 h. Workup according to the general procedure and flash column chromatography on silica (12 g, 2-10% EtOAc/hexanes) afforded the title compound as a colorless oil (116 mg, 77% yield). Rf=0.21 (10% EtOAc/hexanes); 1H NMR (500 MHz, CDCl3) delta 7.83 (d, J=8.0 Hz, 2H), 7.70 (d, J=16.1 Hz, 1H), 7.53 (d, J=8.2 Hz, 2H), 6.50 (d, J=16.0 Hz, 1H), 4.27 (q, J=7.1 Hz, 2H), 1.36 (s, 12H), 1.34 (t, J=7.0 Hz, 3H); 13C NMR (125 MHz, CDCl3) delta 167.0, 144.6, 137.1, 135.4, 127.4, 119.3, 84.2, 60.7, 25.0, 14.5; HR-MS (ESI): calcd. For C17H2310BO4 (M+): 301.1731; found: 301.1740. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium acetate; In water; | (R)-4-((tert-Butyldimethylsilyl)oxy)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-butan-2-one Following the general procedure, using (R)-4-(4-bromophenyl)-4-((tert-butyldimethylsilyl)oxy)butan-2-one (179 mg, 0.5 mmol), Pd(PtBu3)2 (7.7 mg, 0.015 mmol), B2pin2 (140 mg, 0.55 mmol), and KOAc (147 mg, 1.5 mmol) in 2 mL of 2% TPGS-750-M/H2O, GC/FID and TLC monitoring indicated complete conversion after an overall reaction time of 9 h. Workup according to the general procedure and flash column chromatography on silica (12 g, 2-10% EtOAc/hexanes) afforded the title compound as a colorless oil (165 mg, 82% yield). Rf=0.25 (10% EtOAc/hexanes); 1H NMR (500 MHz, CDCl3) delta 7.73 (d, J=8.0 Hz, 2H), 7.31 (d, J=8.0 Hz, 2H), 5.13 (dd, J=9.0, 4.0 Hz, 1H), 2.89 (dd, J=14.5, 9.0 Hz, 1H), 2.48 (dd, J=14.5, 4.0 Hz, 1H), 2.11 (s, 3H), 1.31 (s, 12H), 0.81 (s, 9H), -0.03 (s, 3H), -0.22 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 207.2, 147.8, 135.0, 125.3, 83.9, 72.1, 54.4, 32.0, 25.9, 25.1, 25.0, 18.2, -4.5, -5.1; HR-MS(ESI): calcd. For C22H37BO4NaSi (M+Na+): 427.2452; found: 427.2444. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium acetate; In water; | tert-Butyldimethyl((1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-vinyl)oxy)-silane Following the general procedure, using (1-(4-bromophenyl)vinyl)oxy)(tert-butyl)-dimethylsilane (157 mg, 0.5 mmol), Pd(PtBu3)2 (7.7 mg, 0.015 mmol), B2pin2 (140 mg, 0.55 mmol), and KOAc (147 mg, 1.5 mmol) in 2 mL of 2% TPGS-750-M/H2O, GC/FID and TLC monitoring indicated complete conversion after an overall reaction time of 2.5 h. Workup according to the general procedure and flash column chromatography on silica (12 g, 3% EtOAc/hexanes) afforded the title compound as a colorless (153 mg, 77% yield). Rf=0.51 (10% EtOc/hexanes); 1H NMR (500 MHz, CDCl3) delta 7.77 (d, J=8.0 Hz, 2H), 7.60 (d, J=8.0 Hz, 2H), 4.95 (s, 1H), 4.47 (s, 1H), 1.35 (s, 12H), 1.00 (s, 9H), 0.20 (s, 6H); 13C NMR (125 MHz, CDCl3) delta=156.1, 140.6, 134.8, 124.7, 84.0, 60.6, 26.0, 25.1, 18.5, -4.4; HR-MS (ESI): calcd. For C20H3310BO3Si (M+): 359.2328; found: 359.2333. |
Tags: 53199-31-8 synthesis path| 53199-31-8 SDS| 53199-31-8 COA| 53199-31-8 purity| 53199-31-8 application| 53199-31-8 NMR| 53199-31-8 COA| 53199-31-8 structure
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H311 | Toxic in contact with skin |
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H316 | Causes mild skin irritation |
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H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H332 | Harmful if inhaled |
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H371 | May cause damage to organs |
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H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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