Home Cart 0 Sign in  

[ CAS No. 96385-23-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 96385-23-8
Chemical Structure| 96385-23-8
Structure of 96385-23-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 96385-23-8 ]

Related Doc. of [ 96385-23-8 ]

Alternatived Products of [ 96385-23-8 ]

Product Details of [ 96385-23-8 ]

CAS No. :96385-23-8 MDL No. :MFCD22124052
Formula : C19H17BF5P Boiling Point : -
Linear Structure Formula :- InChI Key :OTWRLIQGHGHSEI-UHFFFAOYSA-N
M.W : 382.12 Pubchem ID :11303586
Synonyms :

Calculated chemistry of [ 96385-23-8 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.05
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 101.25
TPSA : 13.59 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 6.06
Log Po/w (WLOGP) : 7.31
Log Po/w (MLOGP) : 5.96
Log Po/w (SILICOS-IT) : 5.0
Consensus Log Po/w : 4.87

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.28
Solubility : 0.000203 mg/ml ; 0.000000531 mol/l
Class : Poorly soluble
Log S (Ali) : -6.13
Solubility : 0.000287 mg/ml ; 0.00000075 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.22
Solubility : 0.0000023 mg/ml ; 0.000000006 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.38

Safety of [ 96385-23-8 ]

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:

Application In Synthesis of [ 96385-23-8 ]

* 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 [ 96385-23-8 ]

[ 96385-23-8 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 102195-80-2 ]
  • [ 96385-23-8 ]
  • [ 138958-00-6 ]
  • [ 138957-99-0 ]
  • 2
  • tricyclohexyl(hydroxymethyl)phosphonium tetrafluoroborate [ No CAS ]
  • [ 96385-23-8 ]
YieldReaction ConditionsOperation in experiment
73% With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 20℃; The compound 1 (150 g, 0.396 mol) was dissolved in dichloromethane (1.5 L) and cooled to 0 C. To the reaction system, DAST (191 g, 1.187 mol) was slowly dripped. Then the reaction solution was raised to room temperature and reacted overnight. The reaction solution was quenched by pouring into ice water. The resulting mixture was extracted with dichloromethane. The obtained organic phases were combined, washed once by water (500 mL) and saturated saline solution (500 ml) respectively, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was dissolved with dichloromethane (350 mL) under heating, and then was slowly dripped into petroleum ether while stirring. During the process, solid precipitations were accompanied. The solids were filtered and dried in drying oven (50 C) overnight to give the product fluoromethyl triphenylphosphonium tetrafluorofluoroborate (110 g, 73%).
58.39% With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 15℃; for 16h; To the mixture of (hydroxymethyl)triphenylphosphonium tetrafluoroborate (184 g, 484.05 mmol) in DCM (85 mL), DAST (64 mL, 484.05 mmol) was added dropwise at 0 C and then the reaction mixture was stirred at room tempearture (5-15 C) overnight (l6h). The reaction mixture was diluted with ice H20 (960 mL) and separated, the organic phase was dried over Na2S04 and filtered. The filtrate was mixed with TBME (300 mL) to recrystallize the product. After overnight, more crystals precipitated out, filtered and the filter cake was dried under reduced pressure. Compound (0336) (fluoromethyl)triphenylphosphonium tetrafluoroborate (108 g, yield: 58.39%, BF4) was obtained as a light yellow solid. 1H NMR (400MHz, DMSO-rfc) d 7.87 - 7.70 (m, 15H), 6.29 (d, 7 = 45.2 Hz, 2H).
44% With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 20℃; for 1h; (Hydroxymethyl)triphenylphosphonium tetrafluoroborate (11.4 g, 0.03 mol, 1.0 eq),Dissolved in anhydrous dichloromethane(100 mL), the temperature was lowered to 0 degree, DAST (7.2 mL, 0.06 mol, 2.0 eq) was slowly added dropwise, and the reaction was resumed at room temperature for 1 hour.The reaction was completely detected by TLC, and the temperature was lowered to 0 degree. The reaction was quenched by slowly adding water (30 mL), and the mixture was separated, dried and concentrated.The crude product was subjected to silica gel column chromatography (100-200 mesh silica gel,Purified by methanol/dichloromethane = 0-10%)Recrystallized from diethyl ether / dichloromethane,Obtained as a brown solid (5.0 g, yield: 44%).
With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 20℃; for 20h; DAST (37.85 g, 234.79 mmol, 31.02 mL) was slowly added dropwise to a dichloromethane (400 mL) solution of the compound BB-1-2 (85.00 g, 223.61 mmol) at 0 C. After the addition was completed, the reaction solution was stirred at 20 C for 20 hours. After the completion of the reaction, the reaction was quenched with water (250 mL), the system was stirred at 0 C for 15 minutes, the organic layer was separated, washed with 250 mL 5% sodium bicarbonate aqueous solution, and concentrated under reduced pressure to obtain a crude product, and the crude product was recrystallized with diethyl ether: dichloromethane = 1:1 (600 mL) to obtain the target product BB-1. 1H NMR (400MHz, CDCl3) delta: 7.83-7.94 (m, 2H), 7.66-7.79 (m, 9H), 7.41-7.57 (m, 2H), 7.08-7.22 (m, 2H), 6.22-6.40 (m, 1H), 3.65-3.73 (m, 1H).

  • 3
  • C37H30FP2(1+)*BF4(1-) [ No CAS ]
  • [ 96385-23-8 ]
  • [ 791-28-6 ]
  • 4
  • [ 100-52-7 ]
  • [ 96385-23-8 ]
  • [ 351-78-0 ]
  • 5
  • [ 69131-35-7 ]
  • [ 96385-23-8 ]
  • [ 217805-13-5 ]
  • 6
  • [ 96385-23-8 ]
  • 3-n-hexylcyclobutanone [ No CAS ]
  • [ 217805-09-9 ]
  • 7
  • [ 591-50-4 ]
  • [ 96385-23-8 ]
  • [ 68-12-2 ]
  • [ 351-78-0 ]
  • 8
  • [ 769092-24-2 ]
  • [ 96385-23-8 ]
  • (Z)-1-[(dimethylamino)methyl]-2-fluoromethylidenecyclohexane [ No CAS ]
  • [ 444334-14-9 ]
  • 9
  • [ 769092-24-2 ]
  • [ 96385-23-8 ]
  • [ 444334-14-9 ]
  • 10
  • [ 7673-68-9 ]
  • [ 96385-23-8 ]
  • (Z)-7-(2-fluoroethenyl)dibenzobicyclo[2.2.2]octa-2,5-diene [ No CAS ]
  • (E)-7-(2-fluoroethenyl)dibenzobicyclo[2.2.2]octa-2,5-diene [ No CAS ]
  • 11
  • [ 7353-59-5 ]
  • [ 96385-23-8 ]
  • [ 362014-42-4 ]
  • [ 362014-40-2 ]
  • 12
  • S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulphonium tetrafluoroborate [ No CAS ]
  • [ 603-35-0 ]
  • [ 96385-23-8 ]
  • 13
  • [ 88410-12-2 ]
  • [ 96385-23-8 ]
  • 14
  • [ 603-35-0 ]
  • thiocyanato [ No CAS ]
  • [ 96385-23-8 ]
  • 15
  • [ 96385-23-8 ]
  • [ 80474-45-9 ]
  • [ 80474-14-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In acetonitrile; at 20℃; 1 g (2.13 mmol) of 17- propionate carbothioic acid was suspended in 12 ml of acetonitrile. 0.45 g (0.65 eq) of cesium carbonate and 1.4 g (1 .7 eq) of P- mono<strong>[96385-23-8]fluoromethyltriphenylphosphonium tetrafluoroborate</strong> were added. The mixture was stirred at room temperature until the reaction is complete. The solid was isolated by filtration, washed twice with 3 ml of acetonitrile previously cooled to 5 C and then with 3 ml of water. The solid was dried under vacuum at a temperature below 35 C.
  • 16
  • [ 96385-23-8 ]
  • [ 184429-84-3 ]
  • tert-butyl (2-(((tert-butyldimethylsilyl)oxy)methyl)-3-fluoroallyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% (Fluoromethyl)triphenylphosphonium tetrafluoroborate (5.0 g, 13.1 mmol, 1.5 eq) was dissolved in anhydrous water under nitrogen.In THF (50 mL), the mixture was cooled to -20 C, and NaHMDS (1.6 M, 6.5 mL, 10.45 mmol, 1.5 eq) was slowly added dropwise.Add the insulation for 10 minutes.Slowly adding (3-((tert-butyldimethylsilyl)oxy)-2-oxopropyl)carbamic acid tert-butyl ester(2.64 g, 8.7 mmol, 1.0 eq) in THF (5 mL)After the incubation for 1 hour, the temperature was returned to room temperature, and the reaction was completely detected by LC-MS.The reaction was quenched by dropwise addition of water (10 mL), and the mixture was concentrated to viscous liquid.Add water (50 mL) and extract with ether (50 mL) three times.Combine the organic phases, dry and concentrate.The crude product was subjected to silica gel column chromatography (100-200 mesh silica gel,Purified colorless viscous liquid by petroleum ether / ethyl acetate = 0-30%(cis-trans isomer mixture, 4.0 g, 97%).
94% To a vigorously stirring suspension of fluoromethyl(triphenyl)-phosphonium tetrafluoroborate (18.9 g, 49.4 mmol) in dry THF (190 mL) at -20 C under N2 was added sodium bis(trimethylsilyl)amide (1.0 M in THF; 49.4 niL, 49,4 mmol) slowly over 10 min. The resulting deep orange solution was left to stir at this temperature for 15 min. A solution of <strong>[184429-84-3]tert-butyl 3-(tert-butyldimethylsilyloxy)-2-oxopropylcarbamate</strong> (10.0 g, 33.0 mmol) in THF (10 mL) was then added slowly over 10 min. After complete addition, stirring was continued for a further 1 h during which time the reaction was allowed to warm slowly to room temperature. The reaction was quenched by addition of water (5 mL) and the reaction mixture was concentrated in vacuo. The residue was partitioned between water (100 mL) and diethyl ether (100 mL) and the aqueous layer was extracted with further diethyl ether (2 x 100 ml). The combined organics were dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified over silica gel eluting with n-hexane followed by 6 % ethylacetate in n-hexane to give tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-fluoroallylcarbamate as a mixture of E/Z double-bond isomers (E/Z = 1:1; 9.9 g, 94%). The isomers were not separated at this stage.
76.7% To a suspension of (fluoromethyl)triphenylphosphonium tetrafluoroborate (32.74 g, 85.68 mmol, BF4) in THF (200 mL) at -78 C under N2 was added NaHMDS (1M, 85.68 mL) over 30 min, the mixture was stirred for lh at -78 C. A solution of compound 12B (13 g, 42.84 mmol) in THF (50 mL) was added slowly. After addition, the mixture was stirred for 20h at -78 C. The reaction mixture was quenched by water (300 mL), concentrated to remove THF, then extracted with TBME (100 mL x 3), the organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated to give a residue. The residue was purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, Eluent of 0 ~ 10% Ethyl acetate/Petroleum ether gradient 85 mL/min). Compound 12C (10.5 g, yield: 76.7%) as light yellow oil was obtained. 'H NMR (400MHz, CDCb) d 6.66 - 6.39 (m, 1H), 4.82 (s, 1H), 4.02 (dd, / = 1.2, 4.4 Hz, 2H), 3.82 (d, J = 3.4 Hz, 2H), 1.36 (s, 9H), 0.82 (s, 9H), 0.01 (s, 6H).
  • 17
  • (2S,3S,4aR,8S,8aR)-tert-butyl 8-formyl-2,3-dimethoxy-2,3-dimethyltetrahydro-2H-spiro[[1,4]dioxino[2,3-c]pyridine7,1'-cyclopropane]-6(3H)-carboxylate [ No CAS ]
  • [ 96385-23-8 ]
  • (2S,3S,4aR,8S,8aR)-tert-butyl 8-((Z)-2-fluorovinyl)-2,3-dimethoxy-2,3-dimethyltetrahydro-2H-spiro[[1,4]dioxino[2,3-c]pyridine-7,1'-cyclopropane]-6(3H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% [00150j A freshly prepared solution of lithium diisoproylamide (2.26 mmol) in anhydrous THF (8 mL) was added slowly to a stirred suspension of (fluoromethyl)triphenylphosphoniumtetrafluoroborate (0.86 g, 2.26 mmol) at -78C under N2. The mixture was stirred at 0 C for 15 mm and then cooled to -78 C. A solution of(2S,3S,4aR,8S,8aR)-tert-butyl 8-formyl-2,3 -dimethoxy-2,3 -dimethyltetrahydro-2H-spiro [[1,41 dioxino [2,3-cl pyridine7,1?-cyclopropanej-6(3H)-carboxylate (290 mg, 0.75 mmol) was added slowly. The mixture was allowed to warm up to room temperature and stirred for 18 h. The reaction was quenched with saturated aqueous ammonium chloride, and diluted with EtOAc. The organic layer was washed with water, brine, dried, and concentrated. The residue was purified bychromatography to give (2S,3 S,4aR, 8S, 8aR)-tert-butyl 8-((Z)-2-fluorovinyl)-2,3-dimethoxy-2,3 -dimethyltetrahydro-2H-spiro[ [1,41 dioxino [2,3-cl pyridine-7, 1 ?-cyclopropanel -6(3H)-carboxylate (19 mg, 6%) as oil. ?H NMR (400 MHz, CDC13) oe 6.56 (ddd, J= 0.8, 4.8, 83.6Hz, 1H), 4.30-4.00 (m, 2H), 3.75-3.60 (m, 2H), 3.32 (s, 3H), 3.27 (s, 3H), 3.28-3.25 (m, 1H),2.87 (t,J= 11.2 Hz, 1H), 1.48 (s, 9H), 1.33 (s, 3H), 1.32 (s, 3H), 1.20-1.06 (br, 1H), 1.02-0.85 (m, 1H), 0.52-0.35 (m, 2H); MS, (ES, m/z) [M+Najb 424.22.
  • 18
  • (2S,3S,4aR,8S,8aR)-tert-butyl 8-formyl-2,3-dimethoxy-2,3-dimethyltetrahydro-2H-spiro[[1,4]dioxino[2,3-c]pyridine7,1'-cyclopropane]-6(3H)-carboxylate [ No CAS ]
  • [ 96385-23-8 ]
  • (2S,3S,4aR,8S,8aR)-tert-butyl 8-((E)-2-fluorovinyl)-2,3-dimethoxy-2,3-dimethyltetrahydro-2H-spiro[[1,4]dioxino[2,3-c]pyridine-7,1'-cyclopropane]-6(3H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% [00152j A freshly prepared solution of lithium diisoproylamide (2.26 mmol) in anhydrous THF (8 mL) was added slowly to a stirred suspension of (fluoromethyl)triphenylphosphoniumtetrafluoroborate (0.86 g, 2.26 mmol) at -78C under N2. The mixture wasstirred at 0 C for 15 mm and then cooled to -78 C. A solution of(25,35,4aR,85,8aR)-tert-butyl 8-formyl-2,3 -dimethoxy-2,3 -dimethyltetrahydro-2H-spiro [[1,41 dioxino [2,3 -cj pyridine7,1?-cyclopropanej-6(3H)-carboxylate (290 mg, 0.75 mmol) was added slowly. The mixture was allowed to warm up to room temperature and stirred for 18 h. The reaction was quenched with saturated aqueous ammonium chloride, and diluted with EtOAc. The organic layer waswashed with water, brine, dried, and concentrated. The residue was purified by chromatography to give (2S,3 S ,4aR, 8S ,8aR)-tert-butyl 8-((E)-2-fluorovinyl)-2,3-dimethoxy- 2,3 -dimethyltetrahydro-2H-spiro[ [1,41 dioxino [2,3-cl pyridine-7, 1 ?-cyclopropanel -6(3H)- carboxylate (12 mg, 4%) as oil. ?H NMR (400 MHz, CDC13) oe 6.59 (dd, J= 10.8, 84.4 Hz, 1H), 4.75-4.62 (m, 1H), 4.15-3.90 (br, 1H), 3.72-3.55 (m, 2H), 3.31 (s, 3H), 3.26 (s, 3H),2.89 (t,J= 11.2 Hz, 1H), 2.65 (br, 1H), 1.46 (s, 9H), 1.33 (s, 6H), 1.23-1.10 (br, 1H), 1.07-0.95 (m, 1H), 0.60-0.40 (m, 2H); MS, (ES, m/z) [M+Najb 424.22.
  • 19
  • [ 96385-23-8 ]
  • [ 28096-33-5 ]
YieldReaction ConditionsOperation in experiment
With lithium hexamethyldisilazane; In tetrahydrofuran; at -85℃; for 0.5h; Method A: Modified Burton's method [18] was used to prepare phosphonium salt 28 via fluorination of [Ph3PCH2OH]+BF4- with DAST analog - 4-(trifluoro-lambda4-sulfanyl)morpholine. The argon atmosphere was maintained throughout the system during experiment. A mixture of 28 (3.8g, 10mmol) and dry THF (25mL) was cooled to -90C and to resulting slurry 1M solution LHMDS in THF (10mL, 10mmol) was added dropwise under intensive stirring at such a rate to maintain temperature ?-80C. Resulting clear solution was stirred at -85C for 30min and then freshly distilled 21 (1.43g, 11mmol) was added via a syringe. The reaction was allowed to proceed for 1h at this temperature and then overnight at 5C. All volatile products were distilled off in a trap (-78C) to give a solution of 19 in THF, based on NMR data. Fractionation of this solution with an effective column gave fraction (1.5g, bp 28-35C), contained 19 (?60%) and THF (?40%), based on GLC analysis.
  • 21
  • tert-butyl (2-(2-butylbenzo[d]oxazol-6-yl)-2-oxoethyl)carbamate [ No CAS ]
  • [ 96385-23-8 ]
  • tert-butyl (2-(2-butylbenzo[d]oxazol-6-yl)-3-fluoroallyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: To a stirring suspension of <strong>[96385-23-8](fluoromethyl)triphenylphosphonium tetrafluoroborate</strong> (1.5 eq) in THF cooled to -5 C was added 1.5M NaHMDS (1.5 eq) dropwise, the reaction was stirred for 15 minutes at -5 C. A ketone (1 eq) in THF was added dropwise. The reaction was allowed to warm to 18 C and was stirred for 30 minutes. The reaction was diluted with water extracted with EtOAc, combined organics were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude residue obtained was purified by automated FCC to the desired product.
  • 22
  • tert-butyl (3-(2-butylbenzo[d]oxazol-6-yl)-2-oxopropyl)carbamate [ No CAS ]
  • [ 96385-23-8 ]
  • tert-butyl (2-((2-butylbenzo[d]oxazol-6-yl)methyl)-3-fluoroallyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% tert- butyl (2-((2-butylbenzo[d]oxazol-6-yl)methyl)-3-fluoroallyl)carbamate was prepared according to the following procedure. To a stirring suspension of <strong>[96385-23-8](fluoromethyl)triphenylphosphonium tetrafluoroborate</strong> (331 mg, 0.61 mmol) in THF (5 mL) cooled to -5 C was added 1.5M NaHMDS (0.54 mL) dropwise, the reaction was stirred for 15 minutes at -5 C. tert- butyl (3-(2-butylbenzo[d]oxazol-6-yl)-2-oxopropyl)carbamate (140 mg, 0.40 mmol) in THF (2 mL) was added dropwise. The reaction was allowed to warm to 18 C and was stirred for 30 minutes. The reaction was diluted with water (10 mL), extracted with EtOAc (2x10 mL), combined organics were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude residue obtained was purified by automated FCC to afford tert- butyl (2-((2-butylbenzo[d]oxazol-6-yl)methyl)-3- fluoroallyl)carbamate (72 mg, 49%) as a yellow oil. LCMS (General 4): RT: 1.59 min; Yield: 44 %; M/z 363.4 (M+FL). and RT: 1.61 min; Yield: 51 %; m/z 363.4 (M+H+).
Same Skeleton Products
Historical Records