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[ CAS No. 324-94-7 ] {[proInfo.proName]}

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Chemical Structure| 324-94-7
Chemical Structure| 324-94-7
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Product Details of [ 324-94-7 ]

CAS No. :324-94-7 MDL No. :MFCD01830385
Formula : C12H9FO Boiling Point : -
Linear Structure Formula :- InChI Key :QSJNKJGPJVOGPK-UHFFFAOYSA-N
M.W : 188.20 Pubchem ID :345420
Synonyms :

Calculated chemistry of [ 324-94-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.86
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 3.3
Log Po/w (WLOGP) : 3.62
Log Po/w (MLOGP) : 3.48
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 3.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.0417 mg/ml ; 0.000222 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.0748 mg/ml ; 0.000398 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.62
Solubility : 0.00451 mg/ml ; 0.000024 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 324-94-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 324-94-7 ]

* 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.

  • Downstream synthetic route of [ 324-94-7 ]

[ 324-94-7 ] Synthesis Path-Downstream   1~85

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  • [ 462-06-6 ]
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  • [ 324-94-7 ]
  • [ 321-62-0 ]
  • [ 64465-61-8 ]
  • 4
  • [ 106-41-2 ]
  • [ 352-33-0 ]
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  • [ 1026851-39-7 ]
  • [ 135136-30-0 ]
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  • [ 324-94-7 ]
  • 4-[2-(4-Propyl-cyclohexyl)-ethyl]-cyclohexanecarbonyl chloride [ No CAS ]
  • 4-[2-(4-Propyl-cyclohexyl)-ethyl]-cyclohexanecarboxylic acid 4'-fluoro-biphenyl-4-yl ester [ No CAS ]
  • 8
  • [ 540-38-5 ]
  • [ 460-00-4 ]
  • [ 324-94-7 ]
  • [ 398-23-2 ]
  • 9
  • [ 352-34-1 ]
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  • [ 330-84-7 ]
  • [ 92-69-3 ]
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  • [ 134023-60-2 ]
  • [ 80254-62-2 ]
YieldReaction ConditionsOperation in experiment
55% With dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II); potassium hydroxide; In 1,4-dioxane; at 70℃; for 5h;Inert atmosphere; Schlenk technique; General procedure: Referring to Scheme IX, a 10-mL round bottom flask equipped with a stir-bar was charged with 4-bromophenol (500 mg, 2.89 mmol, 1.0 equiv.), Pd-PEPPSI-IPent (45 mg, 2 mol %), 2- naphthylboronic acid (745 mg, 4.33 mmol, 1.5 equiv.), and potassium hydroxide (970 mg, 17.3 mmol, 6.0 equiv.). The flask was sealed with a rubber septum and purged with argon (3x). (0466) Dioxane (6.0 mL) was then added via syringe and the reaction was stirred at 70C for 5 h. The reaction mixture was diluted with diethyl ether (75 mL) and washed with 0.1N HCl (2 x 25 mL), water (2x 25 mL) and brine (25 mL). Dried over anhydrous MgSO4 and filtered. The contents were concentrated under reduced pressure and the crude was passed through a pad of silica washing with ethyl acetate to give 3-(naphthalen-2-yl)phenol (569 mg, 89%) as an off-white solid 1H-NMR (400 MHz, CDCl3) ^: 7.98 (s, 1H), 7.87 (m, 3H), 7.72 (m, 1H), 7.60 (d, 2H), 7.48 (m, 2H), 6.95 (d, 2H).
  • 13
  • aqueous diazotized 4'-fluoro-4-amino-biphenyl [ No CAS ]
  • [ 324-94-7 ]
  • 14
  • [ 106-41-2 ]
  • [ 1765-93-1 ]
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YieldReaction ConditionsOperation in experiment
67% With palladium diacetate; potassium carbonate; In water; at 25℃; for 2h; Distilled water and 3 ml 4-Bromo phenol 173 mg (1 mmol) and 4-fluorophenylboronic acid 147 mg (1 mmol) was dissolved potassium carbonate and 415mg (3 mmol) and palladium acetate 1 mg to put 2 hours at room temperature ( was stirred at 25 ). the reaction is complete the solid is filtered dichloromethane to give washed several times, the organic layer was dried over anhydrous magnesium sulfate, then filtered and dried under reduced pressure and purified by column chromatography (diethyl ether / hexane = 1/9) to obtain to give the title compound (127 mg, yield = 67%).
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  • 19
  • [ 74124-79-1 ]
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  • C17H12FNO5 [ No CAS ]
  • 21
  • [ 324-94-7 ]
  • 4'-fluorobiphenyl-4-yl methyl(3-(pyridin-4-yl)benzyl)carbamate [ No CAS ]
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  • [ 324-94-7 ]
  • 3-{4-[2-(4'-fluoro-biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid [ No CAS ]
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  • [ 324-94-7 ]
  • 2-ethoxy-3-{4-[2-(4'-fluoro-biphenyl-4-yloxy)-ethoxy]-phenyl}-propionic acid [ No CAS ]
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  • [ 324-94-7 ]
  • (Z)-3-{4-[2-(4'-Fluoro-biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-acrylic acid ethyl ester [ No CAS ]
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  • [ 324-94-7 ]
  • (Z)-2-Ethoxy-3-{4-[2-(4'-fluoro-biphenyl-4-yloxy)-ethoxy]-phenyl}-acrylic acid ethyl ester [ No CAS ]
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  • [ 324-94-7 ]
  • 2-cyclopentyloxy-3-{4-[2-(4'-fluoro-biphenyl-4-yloxy)-ethoxy]-phenyl}-propionic acid [ No CAS ]
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  • [ 324-94-7 ]
  • (Z)-2-Cyclopentyloxy-3-{4-[2-(4'-fluoro-biphenyl-4-yloxy)-ethoxy]-phenyl}-acrylic acid ethyl ester [ No CAS ]
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  • [ 106-41-2 ]
  • isobutyl halide [ No CAS ]
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  • [ 324-94-7 ]
  • 1-Cyclopropylmethyl-4-(4'-fluoro-biphenyl-4-yloxymethyl)-piperidine [ No CAS ]
  • 37
  • [ 324-94-7 ]
  • [ 627-18-9 ]
  • [ 173025-57-5 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate; In acetonitrile; EXAMPLE 7 Preparation of 4-[3-(4-fluorobiphenyl-4'-oxy)propoxy]-1,3-diaminobenzene (20) STR13 Using 2.8 g (14.9 mmol) of 4-fluoro-4'-hydroxybiphenyl, 50 ml of acetonitrile, 2.17 g (15.6 mmol) of 3-bromopropanol and 4.11 g (30 mmol) of anhydrous potassium carbonate, synthetic treatment was carried out in the same manner as in Example 2. The obtained colorless powder was recrystallized from benzene/n-hexane to obtain 3.26 g (yield: 89%) of 4-fluoro-4'-(3-hydroxypropoxy)biphenyl (18) as a colorless powder.
  • 38
  • hexanes-ethyl acetate [ No CAS ]
  • [ 540-38-5 ]
  • [ 1765-93-1 ]
  • [ 324-94-7 ]
YieldReaction ConditionsOperation in experiment
46% With caesium carbonate;tetrakis(triphenylphosphine)palladium (0); In N,N-dimethyl-formamide; Step 1: 4-(4-fluorophenyl)phenol. A mixture under N2 in DMF (18 mL) of 4-iodophenol (2.00 g, 9.09 mmol), 4-fluorophenylboronic acid (1.40 g, 10.0 mmol), cesium carbonate (4.44 g, 13.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.27 g, 0.23 mmol) was stirred for 10 minutes at ambient temperature and then overnight at reflux. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, and extracted twice with water. The organic phase was washed with brine, dried over Na2 SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (10:1, then 5:1 hexanes-ethyl acetate) gave 4-(4-fluorophenyl)phenol (0.79 g, 46%) as a white powder.
  • 39
  • [ 324-94-7 ]
  • β-(4-hexyloxyphenyl)propionic acid chloride [ No CAS ]
  • [ 100832-49-3 ]
YieldReaction ConditionsOperation in experiment
48% In pyridine; ethanol; water; toluene; EXAMPLE 1 Preparation of 4'-fluoro-4-biphenylyl alpha-methyl-beta-(4-hexyloxyphenyl)propionate 4-Hydroxy-4'-fluorobiphenyl (2.1 g, 0.012 mol) was dissolved in pyridine (10 ml), and to the solution was added beta-(4-hexyloxyphenyl)propionic acid chloride (3.0 g, 0.01 mol) with sufficient shaking, followed by allowing the resulting reaction solution to stand overnight, thereafter pouring it in water (100 ml), extracting the resulting oily material with toluene (100 ml), washing the toluene layer with 6N-HCl and then with 2N-NaOH, further washing with water till the washing liquid became neutral, filtering, distilling off toluene under reduced pressure, and recrystallizing residual crystals from ethanol to obtain the objective 4'-fluoro-4-biphenylyl alpha-methyl-beta-(4-hexyloxyphenyl)propionate (2.1 g, yield 48%). m.p.: 78.4-79.5 C. N-I point: 38.1 C.
  • 40
  • [ 324-94-7 ]
  • [ 220614-64-2 ]
YieldReaction ConditionsOperation in experiment
Example 19B N-[1-[[(4'-fluoro[1,1'-biphenyl]-4-yl)oxy]methyl]-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-N-hydroxyformamide Prepared according to the sequence of reaction described in examples 5D through 5H, substituting 19A for 5C in example 5D and 4-(4'-fluorophenyl)-phenol for 4'-hydroxy-4-biphenyl carbonitrile in example 5F. 1H NMR (300 MHz, d6-DMSO) delta 9.86 (S, 0.5H), 9.54 (S, 0.5H), 8.31 (S, 0.5H), 7.91 (S, 0.5H), 7.67-7.57 (M, 6H), 7.27-7.22 (M, 3H), 7.01-6.97 (M, 3H), 4.96-4.70 (M, 0.5H), 4.50-4.40 (M, 0.5H), 4.18-4.08 (M, 3H), 3.77-3.73 (M, 2H), 2.79 (S, 6H), 1.28 (S, 12H). MS (ESI) m/e 430 (M+H), 428 (M-H). Anal. Calcd for: C22H24N3O5F·0.5H2O: C, 60.26; H, 5.74; N, 9.58. Found: C, 60.48; H, 5.66; N, 8.72.
EXAMPLE 19B N-[1-[[(4'-fluoro [1,1'-biphenyl]-4-yl)oxy]methyl]-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-N-hydroxyformamide Prepared according to the sequence of reaction described in examples 5D through 5H, substituting 19A for 5C in example 5D and 4-(4'-fluorophenyl)-phenol for 4'-hydroxy-4-biphenyl carbonitrile in example 5F. 1H NMR (300 MHz, d6-DMSO) delta 9.86 (S, 0.5H), 9.54 (S, 0.5H), 8.31 (S, 0.5H), 7.91 (S, 0.5H), 7.67-7.57 (M, 6H), 7.27-7.22 (M, 3H), 7.01-6.97 (M, 3H), 4.96-4.70 (M, 0.5H), 4.50-4.40 (M, 0.5H), 4.18-4.08 (M, 3H), 3.77-3.73 (M, 2H), 2.79 (S, 6H), 1.28 (S, 12H). MS (ESI) m/e 430 (M+H), 428 (M-H); Anal. Calcd for: C22H24N3O5F.0.5H2O: C, 60.26; H, 5.74; N, 9.58. Found: C, 60.48; H, 5.66; N, 8.72.
  • 41
  • [ 886527-07-7 ]
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  • 2-[(4-{2-[(4'-fluorobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 0 - 20℃; for 17h; [Example 34] 2-[(4-{2-[(4'-fluorobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid (Example 34-1) 2-[(4-{2-[(4'-fluorobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester; [Show Image] 2-[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (451 mg) synthesized in Example 4 and 4'-fluorobiphenyl-4-ol (280 mg) were dissolved in tetrahydrofuran (10 mL), triphenylphosphine (430 mg) and diisopropyl azodicarboxylate (40% toluene solution, 0.88 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 17 hr. The reaction mixture was concentrated under reduced pressure, and hexane (about 10 mL) was added. The precipitated crystals were removed by filtration, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (390 mg) as a colorless oil. 1H-NMR (DMSO, 300 MHz) delta: 1.33(9H,s), 1.51(6H,s), 3.18(2H,t,J=6.6Hz), 4.33(2H,t,J=6.6Hz), 7.01 (2H,d,J=9Hz), 7.25(2H, t. J=9Hz), 7.56 (2H,d,J=9Hz), 7.57 (1H,s), 7.61-7.66 (2H, m). MS:474 (M++1).
  • 42
  • [ 1033761-77-1 ]
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  • [ 1033761-78-2 ]
YieldReaction ConditionsOperation in experiment
51% With dicyclohexyl-carbodiimide;dmap; 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; at 20℃; 1.0 g (3.4 mmol) of the compound (Z9) obtained in Example 9, 0.7 g (3.4 mmol) of 4-fluoro-4'-hydroxybiphenyl, 0.010 g of DMAP and a small amount of BHT were suspended in 10 ml of methylene chloride under stirring at room temperature, to which 0.8 g (3.8 mmol) of DCC dissolved in 5 ml of methylene chloride was added, followed by stirring overnight. The precipitated DCC urea was separated by filtration and the resulting filtrate was successively washed each twice with each 50 ml of 0.5N-HCl, a saturated sodium hydrogen carbonate aqueous solution and a saturated saline solution and dried over magnesium sulfate, after which the solvent was distilled off, followed by purification through recrystallization operation with ethanol to obtain 0.8 g of the compound (Z10) (yield: 51%). 1H-NMR(CDCl3) delta: 1.55-1.90(m, 6H), 2.63(m, 1H), 3.07(m, 1H), 4.06(t, 2H), 4.55(m, 1H), 5.64(d, 1H), 6.24(d, 1H), 6.97(d, 2H), 7.13(m, 2H), 7.26(d, 2H), 7.56(m, 4H), 8.17(d, 2H). The results of observation of a liquid phase of the polymerizable liquid crystal compound (Z10) revealed that upon temperature rise, the compound underwent phase transition into a smectic X phase at 101C and into a nematic phase at 117C, and turned into an isotropic liquid state at 149C.
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  • [ 1233707-12-4 ]
  • C27H24FNO4 [ No CAS ]
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  • 4-hydroxybenzenediazonium tetrafluoroborate [ No CAS ]
  • potassim 4-fluorophenyltrifluoroborate [ No CAS ]
  • [ 324-94-7 ]
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  • [ 324-94-7 ]
  • [ 1228440-57-0 ]
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  • [ 1228440-59-2 ]
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  • [ 324-94-7 ]
  • [ 1228440-56-9 ]
  • [ 1228440-58-1 ]
YieldReaction ConditionsOperation in experiment
With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In water; toluene; for 3h;Reflux; Example 2-1 2-[(4-[(4'-fluorobiphenyl-4-yl)oxy]acetyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester 2-[4-(Chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (23.8 g) and 4'-fluorobiphenyl-4-ol (12.00 g) obtained in Example 1 were dissolved in toluene (650 mL), aqueous sodium hydroxide solution (1 mol/L, 71 mL), tetrabutylammonium iodide (2.62 g) and water (71 mL) were added, and the mixture was heated under reflux for 3 hr, and allowed to cool to perform partitioning. The organic layer was washed twice with 1 mol/L aqueous sodium hydroxide solution (300 mL) and twice with saturated aqueous sodium chloride solution (200 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Moritex Purif Pack SI 60 mum size 200 was used. elution solvent: hexane/ethyl acetate=95/151?70/30) to give the title compound as a pale-yellow oily substance (1.128 g). 1H-NMR (CDCl3,300 MHz) delta: 1.43 (9H, s), 1.68 (6H, s), 5.45 (2H, s), 6.91-7.13 (4H, m), 7.45-7.51 (4H, m), 8.29 (1H, s). LC-MS: 432 (M-tBu+H)+
  • 49
  • [ 324-94-7 ]
  • [ 1228440-67-2 ]
  • [ 1228440-58-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; for 6.33333h;Reflux; Example 10-1 2-[(4-[(4'-fluorobiphenyl-4-yl)oxy]acetyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester The bromoketone compound (10.462 g) obtained in Example 9 was dissolved in acetone (300 ml), 4'-fluorobiphenyl-4-ol (5.17 g) and potassium carbonate (3.80 g) were added and the mixture was heated under reflux for 6 hr 20 min. The solid was filtered off, and the solvent of the filtrate was evaporated. The residue was dissolved in toluene (100 mL), washed 3 times with aqueous sodium hydroxide solution (1 mol/L) (50 ml), washed with saturated brine (50 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by column chromatography (divided in 3 times. Moritex Corporation Purif Pak Si 60 mum, size 200 was used. eluent: hexane/ethyl acetate=90/10-60/40) to give the title compound (7.36 g). 1H-NMR (CDCl3,300 MHz)
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  • [ 1228440-68-3 ]
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  • [ 1228440-69-4 ]
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  • [ 1228440-71-8 ]
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  • [ 324-94-7 ]
  • 2-[(4-{2-[(4'-fluorobiphenyl-4-yl)oxy]-1-methoxyethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester [ No CAS ]
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  • [ 106-95-6 ]
  • [ 134750-80-4 ]
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  • [ 106-41-2 ]
  • [ 106-38-7 ]
  • [ 1765-93-1 ]
  • [ 324-94-7 ]
  • [ 72093-43-7 ]
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  • [ 134750-80-4 ]
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  • [ 106-95-6 ]
  • [ 121721-95-7 ]
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  • [ 1765-93-1 ]
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  • [ 36716-69-5 ]
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  • [ 104-92-7 ]
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  • [ 324-94-7 ]
  • [ 36716-69-5 ]
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  • [ 450-39-5 ]
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  • [ 324-94-7 ]
  • [ 1219467-85-2 ]
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  • [ 324-94-7 ]
  • [ 35770-89-9 ]
YieldReaction ConditionsOperation in experiment
With bromine; In dichloromethane; acetonitrile; at 20℃; for 18h;Inert atmosphere; A solution of bromine (4.57 g, 28.59 mmol) in dichloromethane (20 mL) was added dropwise to a solution of 4-fluoro-4'-hydroxybiphenyl [purchased from TCI] (5.38 g, 28.59 mmol) in dichloromethane (100 mL) and acetonitrile (20 mL) and the reaction mixture stirred at room temperature under nitrogen for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL) containing 10% aqueous sodium thiosulfate solution (20 mL), water (200 mL) and saturated brine (200 mL), dried (MgSO4), filtered and concentrated in vacuo to give crude 3-bromo-<strong>[324-94-7]4'-fluoro-[1,1'-biphenyl]-4-ol</strong> (9.0 g) as a tan solid. HPLC/MS Rt=5.84 min, m/z 265.1 and 267.1 (M-H-).
  • 67
  • [ 324-94-7 ]
  • (R)-2-(2-nitro-6,7-dihydro-5H-imidazol[2,1-b][1,3]oxazin-7-yl)ethanol [ No CAS ]
  • (R)-7-(2-(4'-fluorobiphenyl-4-yloxy)ethyl)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With di-isopropyl azodicarboxylate; triphenylphosphine; In N,N-dimethyl-formamide; at 0 - 20℃; for 10h; General procedure: To a stirred solution of compound 7a or 7b (107mg, 0.5mmol) and triphenylphosphine (197mg, 0.75mmol) and phenol (0.75mmol) in dried DMF (1.5ml) at 0 Cwas added slowly diisopropyl azodicarboxylate (0.148ml, 0.75mmol). Mixture was stirred at room temperature. After 10h, reaction was diluted with water and extracted with EtOAc (3times). Organic layer was dried over MgSO4 and concentrated under vacuum. Generated solid was filted with Et2O. The residue was dried under vaccum to afford the compound 9a-g.
  • 68
  • [ 324-94-7 ]
  • C19H22Cl2N4O3 [ No CAS ]
  • C31H30ClFN4O4 [ No CAS ]
  • 69
  • [ 681490-98-2 ]
  • [ 324-94-7 ]
  • (2S)-2-[(4'-fluoro[1,1'-biphenyl]-4-yl)oxy]methyl}-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole [ No CAS ]
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  • [ 681490-93-7 ]
  • [ 324-94-7 ]
  • (2R)-2-[(4'-fluoro[1,1'-biphenyl]-4-yl)oxy]methyl}-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole [ No CAS ]
  • 71
  • [ 106-41-2 ]
  • [ 17151-47-2 ]
  • [ 324-94-7 ]
YieldReaction ConditionsOperation in experiment
94% With 4,4'-bis(trimethylaminomethyl)-2,2'-bipyridine dihydrobromide; diamminedichloropalladium(II); sodium hydrogencarbonate; In water; at 110℃; for 12h;Sealed tube; General procedure: A sealable tube, equipped with a magnetic stirring bar, was charged with aryl halide (1 mmol), organotin (1.2 mmol), NaHCO3 (2 mmol), and H2O (2 mL). In the case of tetramethyltin, the addition of tetraethylammonium iodide (TEAI, 1 mmol) was required. After the addition of PdCl2(NH3)2/L aqueous solution (1 mL H2O; different concentrations were required for various substrate/catalystratios), the tube was sealed under air using a Teflon-coated screw cap. The reaction vessel was then placed in an oil bath at 110 C for the indicated reaction duration (see Tables 2-4). After cooling of the reaction mixture to room temperature, the aqueous solution was extracted with hexane or ethyl acetate; the organic phase was dried over MgSO4, and the solvent was then removed under vacuum. Column chromatography on silica gel afforded the desired product (see Supplementary Materials for the copies of NMR spectra).
  • 72
  • [ 62573-11-9 ]
  • [ 324-94-7 ]
  • nonaethylene glycol mono(4'-fluoro-4-biphenyl) ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% 7ch (190 mg, 1.01 mmol) was dissolved in THF (2.0 mL). This sodium hydride (mineral oil suspension, purity 60%, 46 mg, 1.15 mmol) was stirred at room temperature for 1 hour added. The stuff 5 (195 mg, 0.31 mmol) was added THF (2.0 mL) solution of was stirred at room temperature for 24 hours. The reaction solution was diluted with ethyl acetate (10 mL), water (10 mL), and the washed successively with saturated brine (10 mL). This was filtered and dried over anhydrous sodium sulfate, and concentrated in an evaporator. The obtained residue was purified by silica gel column chromatography (silica gel:. 6 g, developing solvent: ethyl acetate - methanol mixed solvent pair 0 ? 90: 1 ?. 8-to-1 ? 2: 1) was separated and purified by, 9ch (133 mg, 0.23 mmol, 66% yield).
  • 73
  • [ 324-94-7 ]
  • C26H24BrF13OS [ No CAS ]
  • C38H32F14O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With potassium carbonate; In pentan-3-one; at 110℃; for 24h; Specifically, first, Compound (I) 0.52g (0.73mmol), 4- fluoro-4'-hydroxy-biphenyl 0.14 g (0.73 mmol), potassium carbonate 0.18 g (1.30 mmol), and 3-pentanone 50mL placed in a 200mL eggplant flask, was carried out under reflux for 1 day at 110 C. After completion of the reaction was transferred to stand by separatory funnel to room temperature. There, water was added to the ethyl acetate and brine and separated into an aqueous phase and an organic phase. Then, after it allowed to stand for 30 minutes over anhydrous magnesium sulfate the organic phase, subjected to pleat folding filtered to obtain a filtrate was concentrated with an evaporator solid. The resulting solid was purified by silica gel column chromatography with chloroform to give Compound (8) 0.06g (0.07mmol). The resulting compound (8) is a colorless crystalline, its melting point is 181-182 C, the yield was 10%. Further, the infrared spectrophotometer and a nuclear magnetic resonance device were identified compound (8). The results are shown in the following.
  • 74
  • [ 324-94-7 ]
  • C26H24BrF13OS [ No CAS ]
  • C38H32F14O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With potassium carbonate; In cyclohexanone; at 160℃; for 24h; Specifically, first, the compound (J) 0.52g (3.89mmol), 4- fluoro-4'-hydroxybiphenyl 0.13 g, (0.71 mmol), potassium carbonate 0.15 g (1.10 mmol), and put the cyclohexanone 70mL in 200mL eggplant flask, for 1 day at 160 C, was reflux. After completion of the reaction was transferred to stand by separatory funnel to room temperature. There, subjected to suction filtration with the addition of water 100mL, it was separated into solid and liquid. The resulting solid was washed with ethyl acetate to give compound (9) 0.03g (0.04mmol). The obtained compound (9) is a colorless crystalline, its melting point is 190-191 C, the yield was 6.0%. Further, the infrared spectrophotometer and a nuclear magnetic resonance device were identified compound (9). The results are shown in the following.
  • 75
  • [ 324-94-7 ]
  • C20H20BrF13OS [ No CAS ]
  • C32H28F14O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate; In acetone; at 65℃; for 48h; Specifically, first, the compound (B) 0.60g (0.94mmol), 4- fluoro-4'-hydroxy-biphenyl 0.18 g (0.94 mmol), potassium carbonate 0.18 g (1.30 mmol), and put the acetone 50mL in 200mL eggplant flask, it was carried out under reflux for 2 days at 65 C. After completion of the reaction was transferred to stand by separatory funnel to room temperature. There, the water was separated into aqueous and organic phases by addition of cyclopentyl methyl ether and brine. Then, after it allowed to stand for 30 minutes over anhydrous magnesium sulfate the organic phase, subjected to pleat folding filtered to obtain a filtrate was concentrated with an evaporator solid. The resulting solid was purified by recycle HPLC with chloroform, to give the compound (6) 0.35g (0.47mmol). The obtained compound (6) is a white powder, the melting point is 115-117 C, the yield was 51%. Further, the infrared spectrophotometer and a nuclear magnetic resonance device were identified compound (6). The results are shown in the following.
  • 76
  • [ 563-52-0 ]
  • [ 324-94-7 ]
  • 1-(but-3-en-2-yloxy)-4-(4-fluorophenyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide; In water; N,N-dimethyl-formamide; at 45℃; for 24h; A solution of 4-(4-fluorophenyl)phenol (44) (340 mg, 1.81 mmol) in dry DMF (5 mL) was treated with a solution of NaOH (0.15 g) in water (0.26 mL) followed by 3-chlorobut-1-ene (344 mg, 3.80 mmol). The mixture was stirred at 45 oC for 24 h, diluted with water and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel (hexane/ethyl acetate, 9:1) to yield 66 as an oil (349 mg, 80 %). 1H NMR (400 MHz, CDCl3): delta 1.53 (d, J = 6.4 Hz, 3H), 4.83-4.94 (m, 1H), 5.26 (ddd, J = 10.6 Hz, 1.5 Hz and 1.0 Hz, 1H), 5.37 (ddd, J = 17.4 Hz, 1.6 Hz and 1.0 Hz, 1H), 5.94-6.08 (m, 1H), 6.99-7.07 (m, 2H), 7.09-7.19 (m, 2H), 7.46-7.57 (m, 4H); HRMS (APCI, direct probe) m/z [M+H]+ calculated: 243.1180, found: 243.1220.
  • 77
  • [ 324-94-7 ]
  • [ 36722-01-7 ]
  • 3-(1H-benzotriazol-1-yl)-1-[4-(4-fluorophenyl)phenoxy]propan-2-one [ No CAS ]
  • 78
  • [ 324-94-7 ]
  • [ 36722-01-7 ]
  • 3-(1H-benzotriazol-1-yl)-1-[4-(4-fluorophenyl)phenoxy]propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With dmap; at 100℃; for 2h; General procedure: A mixture of 1-(oxiran-2-ylmethyl)-1H-benzotriazole32 (43) (326 mg, 1.86 mmol), 4-(4-fluorophenyl)phenol (44) (350 mg, 1.86 mmol) and 4-dimethylaminopyridine (75 mg, 0.61 mmol) was heated at 100C for 2 h. The reaction mixture was chromatographed on silica gel (hexane/ethyl acetate 9:1 to 4:6) to yield 3-(1H-benzotriazol-1-yl)-1-[4-(4-fluorophenyl)phenoxy]propan-2-ol as a solid (229 mg, 34%)
  • 79
  • [ 324-94-7 ]
  • 4-(4-fluorophenyl)-1-[1-(oxiran-2-yl)ethoxy]benzene [ No CAS ]
  • 80
  • [ 324-94-7 ]
  • 1-(1H-benzotriazol-1-yl)-3-[4-(4-fluorophenyl)phenoxy]butan-2-ol [ No CAS ]
  • 81
  • [ 324-94-7 ]
  • 1-(1H-benzotriazol-1-yl)-3-[4-(4-fluorophenyl)phenoxy]butan-2-one [ No CAS ]
  • 82
  • [ 324-94-7 ]
  • 4'-fluoro-[1,1'-biphenyl]-4-yl sulfurofluoridate [ No CAS ]
  • 83
  • [ 324-94-7 ]
  • [ 91652-00-5 ]
  • C29H29FO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; In a 500 mL four-necked flask,[MA2] (38.6 g, 126 mmol),4-Fluoro-4'-hydroxybiphenyl [MA13-1] (25 g, 136 mmol),EDC (31 g, 151 mmol), DMAP (630 mg, 6.3 mmol) were dissolved in THF (200 g),Stir at room temperature.Trace the reaction by HPLC and confirm the end of the reactionThe reaction solution was poured into 3 L of distilled water. The precipitated solid was separated by filtration, and the resulting solid was washed with IPA (300 g) and methanol (300 g), and the solid was dried to obtain 50 g of compound [MA13] (yield: 83%).
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