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[ CAS No. 205-39-0 ]

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Product Details of [ 205-39-0 ]

CAS No. :205-39-0 MDL No. :MFCD00046916
Formula : C16H10O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :218.25 g/mol Pubchem ID :-
Synonyms :

Calculated chemistry of of [ 205-39-0 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.23
TPSA : 13.14 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.69
Log Po/w (XLOGP3) : 5.37
Log Po/w (WLOGP) : 4.74
Log Po/w (MLOGP) : 3.68
Log Po/w (SILICOS-IT) : 4.48
Consensus Log Po/w : 4.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.32
Solubility : 0.00105 mg/ml ; 0.00000483 mol/l
Class : Moderately soluble
Log S (Ali) : -5.4
Solubility : 0.00087 mg/ml ; 0.00000398 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.64
Solubility : 0.0000494 mg/ml ; 0.000000226 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.69

Safety of [ 205-39-0 ]

Signal Word:Danger Class:9
Precautionary Statements:P201-P264-P280-P301+P330+P331-P312 UN#:3077
Hazard Statements:H302-H361-H372-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 205-39-0 ]

* 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 [ 205-39-0 ]

[ 205-39-0 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 694-80-4 ]
  • [ 15147-55-4 ]
  • [ 205-39-0 ]
  • [ 142095-78-1 ]
YieldReaction ConditionsOperation in experiment
1: 17% 2: 20% With potassium <i>tert</i>-butylate In ammonia for 3h; Irradiation;
  • 2
  • [ 583-55-1 ]
  • [ 15147-55-4 ]
  • [ 205-39-0 ]
  • [ 142095-77-0 ]
YieldReaction ConditionsOperation in experiment
1: 32% 2: 24% With potassium <i>tert</i>-butylate In ammonia for 3h; Irradiation;
  • 3
  • [ 128916-17-6 ]
  • [ 243-42-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
19% at 650℃; for 1h; Flash vacuum pyrolysis;
at 650℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 4
  • [ 159052-03-6 ]
  • [ 239-30-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
1: 44% 2: 14% at 850℃;
  • 5
  • [ 354816-85-6 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaBH4 / methanol; CH2Cl2 / 2 h / 20 °C 2: Pd-C / triethylene glycol dimethyl ether / 24 h / Heating
  • 6
  • 11c-nitro-2,3,4a,5,11b,11c-hexahydronaphtho[2,1-b]benzo[b]furan-4(1H)-one [ No CAS ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: DBN / tetrahydrofuran / 0.5 h / 0 °C 2: NaBH4 / methanol; CH2Cl2 / 2 h / 20 °C 3: Pd-C / triethylene glycol dimethyl ether / 24 h / Heating
  • 7
  • [ 583-55-1 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 32 percent / t-BuOK / liquid ammonia / 3 h / Irradiation 2: sodium, ethanol
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 96 h / 90 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere 3: palladium diacetate; potassium carbonate; triphenylphosphine / acetonitrile / 48 h / 80 °C / Glovebox; Sealed tube; Inert atmosphere
  • 8
  • [ 15147-55-4 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 17 percent / t-BuOK / liquid ammonia / 3 h / Irradiation 2: sodium, ethanol
Multi-step reaction with 2 steps 1: 32 percent / t-BuOK / liquid ammonia / 3 h / Irradiation 2: sodium, ethanol
Multi-step reaction with 2 steps 1: 45 percent / t-BuOK / liquid ammonia / 3 h / Irradiation 2: sodium, ethanol
  • 9
  • [ 20841-53-6 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
at 1100℃;
  • 10
  • [ 66691-27-8 ]
  • [ 243-42-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
With 2Ag(1+)*CH2O3(2-); Pd(TFA)2 In 1,4-dioxane; dimethyl sulfoxide at 150℃; for 14h; Inert atmosphere; regioselective reaction;
With acethylacetonato(1,5-cyclooctadiene)rhodium(I); potassium iodide In acetic anhydride at 160℃; for 10h; Inert atmosphere; Overall yield = 78 %;
  • 11
  • [ 1993-03-9 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / palladium diacetate / toluene; ethanol 2: potassium carbonate / water
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine)palladium (0) / toluene; ethanol 2: boron tribromide; sodium bicarbonate / dichloromethane; water 3: potassium carbonate / water
Multi-step reaction with 2 steps 1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 6.5 h / 80 - 100 °C / Inert atmosphere 2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 80 °C / Inert atmosphere 2: boron tribromide; sodium hydrogencarbonate / dichloromethane; water / 54 h / 0 - 20 °C / Inert atmosphere 3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 6.5 h / 80 - 100 °C / Inert atmosphere 2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 80 °C / Inert atmosphere 2: boron tribromide; sodium hydrogencarbonate / dichloromethane; water / 0 - 20 °C 3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere

  • 12
  • [ 3401-47-6 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine)palladium (0) / toluene; ethanol 2: boron tribromide; sodium bicarbonate / dichloromethane; water 3: potassium carbonate / water
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 80 °C / Inert atmosphere 2: boron tribromide; sodium hydrogencarbonate / dichloromethane; water / 54 h / 0 - 20 °C / Inert atmosphere 3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 80 °C / Inert atmosphere 2: boron tribromide; sodium hydrogencarbonate / dichloromethane; water / 0 - 20 °C 3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
  • 13
  • [ 573-97-7 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / palladium diacetate / toluene; ethanol 2: potassium carbonate / water
Multi-step reaction with 2 steps 1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / toluene; ethanol; water / 6.5 h / 80 - 100 °C / Inert atmosphere 2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 6.5 h / 80 - 100 °C / Inert atmosphere 2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 6 h / 150 °C / Inert atmosphere
  • 14
  • [ 205-39-0 ]
  • [ 1383607-08-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sec.-butyllithium; 2,3-dimethyl-2,3-diaminobutane / cyclohexane; hexane; tetrahydrofuran / 2 h / -80 °C / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 2 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -80 - 20 °C / Inert atmosphere 1.2: 17 h / -80 - 20 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - 20 °C / Inert atmosphere 1.2: 17 h / -75 - 20 °C / Inert atmosphere 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; ethanol / 12 h / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -75 - 20 °C / Inert atmosphere 1.2: 17 h / -75 °C 1.3: 1 h / 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water; ethanol / 12 h / 90 °C / Inert atmosphere

  • 15
  • [ 205-39-0 ]
  • [ 1382763-43-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium bicarbonate / toluene; cyclohexane; hexane; tetrahydrofuran; nitrogen 2: sodium carbonate / tetrakis(triphenylphosphine)palladium (0) / toluene; hexane; ethanol
Multi-step reaction with 2 steps 1.1: sec.-butyllithium; 2,3-dimethyl-2,3-diaminobutane / cyclohexane; hexane; tetrahydrofuran / 2 h / -80 °C / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 3 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; sec.-butyllithium / cyclohexane; hexane; tetrahydrofuran / 2.5 h / -80 - 20 °C / Inert atmosphere 1.2: 48 h / 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 3 h / 80 °C / Inert atmosphere
  • 16
  • [ 205-39-0 ]
  • [ 1382763-47-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; sec.-butyllithium / cyclohexane; hexane; tetrahydrofuran / 2.5 h / -80 - 20 °C / Inert atmosphere 1.2: 48 h / 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 3 h / 80 °C / Inert atmosphere
  • 17
  • [ 205-39-0 ]
  • [ 1382763-49-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; sec.-butyllithium / cyclohexane; hexane; tetrahydrofuran / 2.5 h / -80 - 20 °C / Inert atmosphere 1.2: 48 h / 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 6 h / 80 °C / Inert atmosphere
  • 18
  • [ 205-39-0 ]
  • [ 1382763-54-3 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: benzo[b]naphtho[1,2-d]furan With 2,3-dimethyl-2,3-diaminobutane; sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -80℃; for 2h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane; cyclohexane at 20℃; for 48h; Inert atmosphere; 1.3 After the air in a 500 mL three-neck flask was replaced with nitrogen, 5.8 g (50 mmol) of tetramethylethylenediamine (TMEDA) and 180 mL of tetrahydrofuran (THF) were placed into the flask, and this solution was cooled to -80° C. Then, 50 mL (50 mmol) of sec-butyl lithium (a 1.0 mol/L solution of cyclohexane and n-hexane) was dripped into this solution with a syringe. After that, this solution was stirred at the same temperature for 30 minutes. Then, 10 g (45 mmol) of benzo[b]naphtho[1,2-d]furan dissolved in 70 mL of THF was added dropwise to this solution with a dropping funnel. After that, this solution was stirred at the same temperature for 2 hours. Then, 11 mL (100 mmol) of trimethyl borate was added to this solution, and the mixture was stirred for 2 days while its temperature was returned to room temperature. After that, the aqueous layer of this mixture was subjected to extraction with ethyl acetate, and the obtained solution of the extract and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine. The organic layer was dried with magnesium sulfate, and after that, this mixture was gravity-filtered. The obtained filtrate was concentrated to give a white solid. A mixed solvent of toluene and hexane was added to the obtained solid, the mixture was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that 9.2 g of a white powder of the object of the synthesis was obtained in 78% yield.
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: hydrogenchloride
  • 19
  • [ 205-39-0 ]
  • [ 1382763-45-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sec.-butyllithium; 2,3-dimethyl-2,3-diaminobutane / cyclohexane; hexane; tetrahydrofuran / 2 h / -80 °C / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: potassium carbonate; tris-(o-tolyl)phosphine / palladium diacetate / ethanol; water / 4 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; sec.-butyllithium / cyclohexane; hexane; tetrahydrofuran / 2.5 h / -80 - 20 °C / Inert atmosphere 1.2: 48 h / 20 °C 2.1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 4 h / 80 °C / Inert atmosphere
  • 20
  • [ 1264712-17-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 6h; Inert atmosphere; 1.2 Into a 1 L three-neck flask were placed 15 g (63 mmol) of 1-(2-fluorophenyl)-2-naphthol, 300 mL of N-methyl-2-pyrrolidone (NMP), and 18 g (130 mmol) of potassium carbonate. The mixture in this flask was stirred at 150° C. for 6 hours under a nitrogen stream. After that, this mixture was cooled down to room temperature and added to about 500 mL of water. The aqueous layer of this mixture was subjected to extraction with ethyl acetate, and the obtained solution of the extract and the organic layer were combined and washed with water and saturated brine. The organic layer was dried with magnesium sulfate, and after that, this mixture was gravity-filtered. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (developing solvent: hexane) to give an oily substance. The obtained oily substance was dried under reduced pressure, so that 11.8 g of a colorless transparent oily substance of the object of the synthesis was obtained in 86% yield.
86% With potassium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 6h; Inert atmosphere; 1-1-2 [Step 1-1-2] Synthesis of Benzo[b]naphtho[1,2-d]furan Into a 1 L three-neck flask were placed 15 g (63 mmol) of 1-(2-fluorophenyl)-2-naphthol, 300 mL of N-methyl-2-pyrrolidone (NMP), and 18 g (130 mmol) of potassium carbonate. The mixture in this flask was stirred at 150° C. for 6 hours under a nitrogen stream. After that, this mixture was cooled down to room temperature and added to about 500 mL of water. The aqueous layer of this mixture was subjected to extraction with ethyl acetate, and the obtained solution of the extract and the organic layer were combined and washed with water and saturated brine. The organic layer was dried over magnesium sulfate, and after that, this mixture was gravity-filtered. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (developing solvent: hexane) to give an oily substance. The obtained oily substance was dried under reduced pressure, so that 11.8 g of a colorless transparent oily substance of the object of the synthesis was obtained in 86% yield. The above-described synthesis scheme is illustrated in the following scheme (B-2).
  • 21
  • [ 205-39-0 ]
  • [ 121-43-7 ]
  • [ 1382763-54-3 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: benzo[b]naphtho[1,2-d]furan With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hydrogencarbonate In tetrahydrofuran; hexane; cyclohexane at -80 - 20℃; for 2.5h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane; cyclohexane at 20℃; for 48h; Stage #3: With hydrogenchloride In water 1-1-3 [Step 1-1-3] Synthesis of Benzo[b]naphtho[1,2-d]furan-6-boronic acid After the air in a 500 mL three-neck flask was replaced with nitrogen, 5.8 g (50 mmol) of tetramethylethylenediamine (TMEDA) and 180 mL of tetrahydrofuran (THF) were placed into the flask, and this solution was cooled to -80° C. Then, 50 mL (50 mmol) of sec-butyl lithium (a 1.0 mol/L solution of cyclohexane and n-hexane) was dripped into this solution with a syringe. After that, this solution was stirred at the same temperature for 30 minutes. Then, 10 g (45 mmol) of benzo[b]naphtho[1,2-d]furan dissolved in 70 mL of THF was added dropwise to this solution with a dropping funnel. After that, this solution was stirred at the same temperature for 2 hours. Then, 11 mL (100 mmol) of trimethyl borate was added to this solution, and the mixture was stirred for 2 days while its temperature was returned to room temperature. After that, the aqueous layer of this mixture was subjected to extraction with ethyl acetate, and the obtained solution of the extract and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine. The organic layer was dried over magnesium sulfate, and after that, this mixture was gravity-filtered. The obtained filtrate was concentrated to give a white solid. Toluene/hexane was added to the obtained solid, the mixture was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that 9.2 g of a white powder of the object of the synthesis was obtained in 78% yield. The above-described synthesis scheme is illustrated in the following scheme (B-3).
  • 22
  • [ 205-39-0 ]
  • C22H14O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; sec.-butyllithium / cyclohexane; hexane; tetrahydrofuran / 2.5 h / -80 - 20 °C / Inert atmosphere 1.2: 48 h / 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 2 h / 80 °C / Inert atmosphere
  • 23
  • [ 205-39-0 ]
  • 6-(9,10-diphenyl-2-anthryl)-benzo[b]naphtho[1,2-d]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; sec.-butyllithium / cyclohexane; hexane; tetrahydrofuran / 2.5 h / -80 - 20 °C / Inert atmosphere 1.2: 48 h / 20 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 6 h / 80 °C / Inert atmosphere
  • 24
  • [ 1400883-62-6 ]
  • [ 243-42-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; caesium carbonate; cesium pivalate; 1,2-bis-(dicyclohexylphosphino)ethane In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 17h; Glovebox; Sealed tube; Overall yield = 84 %; Overall yield = 60.1 mg;
  • 25
  • [ 1440730-11-9 ]
  • [ 243-42-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
65% With bis(1,5-cyclooctadiene)nickel(0); caesium carbonate; 1,2-bis-(dicyclohexylphosphino)ethane In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 72h; 4.5.2.8. Naphtho[2,3-b]benzofuran (8a) Table 2, entry 8 4.5.2.8. Naphtho[2,3-b]benzofuran (8a) Table 2, entry 8. Followinggeneral procedure A, pivalate 8-OPiv (100 mg, 0.312 mmol,1.0 equiv), Ni(COD)2 (10.7 mg, 0.039 mmol, 0.125 equiv), dcype(33.0 mg, 0.078 mmol, 0.25 equiv), Cs2CO3 (254 mg, 0.780 mmol,2.5 equiv), and xylene (2.5 mL) were combined in a 20 mL scintillationvial. The reactionmixturewas allowed to stir at 160 C for 72h.The ratio of 8a:8b was determined by GC analysis of the crude reactionmixture and was determined to be 2.9:1. Chromatography ona silica gel column using 98/2 hexanes/DCM yielded product asa mixture of 8a and 8b.24 The yield of the desired product (8a8b)was 65% (44.2 mg).Major isomer (8a): 1H NMR (CDCl3): d 8.43 (br s, 1H), 8.12e8.02(multiple peaks, 2H), 7.99 (d, J8.5 Hz, 1H), 7.94 (br s, 1H), 7.63e7.46(multiple peaks, 4H), 7.39 (t, J7.3 Hz, 1H). The spectroscopic data isconsistent with that reported in the literature.25Minor isomer (8b): 1H NMR (CDCl3): d 8.65 (d, J7.9 Hz, 1H), 8.42(dd, J7.0, 1.7 Hz, 1H), 8.05 (d, J8.0 Hz, 1H), 7.95 (d, J8.7 Hz, 1H),7.79 (d, J8.9 Hz, 1H), 7.77e7.70 (multiple peaks, 2H), 7.57 (t,J7.6 Hz, 1H), 7.53e7.49 (multiple peaks, 2H).
  • 26
  • [ 92964-67-5 ]
  • [ 243-42-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 15 h / 20 °C / Schlenk technique; Inert atmosphere 2: bis(1,5-cyclooctadiene)nickel(0); 1,2-bis-(dicyclohexylphosphino)ethane; caesium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 72 h / 160 °C
Multi-step reaction with 2 steps 1: pyridine / 12 h / 45 °C / Sealed tube 2: palladium diacetate; caesium carbonate; cesium pivalate; 1,2-bis-(dicyclohexylphosphino)ethane / 5,5-dimethyl-1,3-cyclohexadiene / 17 h / 140 °C / Glovebox; Sealed tube
  • 27
  • C17H14O4S [ No CAS ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
81% With rubidium carbonate; palladium diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In 5,5-dimethyl-1,3-cyclohexadiene at 140℃;
  • 28
  • [ 479669-16-4 ]
  • [ 243-42-5 ]
  • [ 205-39-0 ]
YieldReaction ConditionsOperation in experiment
1: 47% 2: 8% With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In N,N-dimethyl-formamide at 145℃; for 18h; Inert atmosphere;
  • 29
  • [ 205-39-0 ]
  • benzo[b]naphtho[1,2-d]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; fluorosulfonylchloride In dichloromethane-d2 at -70℃;
  • 30
  • [ 205-39-0 ]
  • 6-iodobenzo[b]naphtho[1,2-d]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: benzo[b]naphtho[1,2-d]furan With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -80 - 20℃; for 17h; 1.1 Synthesis of 6-iodobenzo[b]naphtho[ 1 ,2-d]furan Into a 500 mL three-neck flask were put 12 g (55 mmol) of benzo[b]naphtho[1,2-d]furan and 220 mL of tetrahydrofuran, and the air in the flask was replaced with nitrogen. Then, this solution was cooled to -80 °C. Then, 40 mL (64 mmol) of n-butyllithium (a 1.6 mol/L n-hexane solution) was dropped into this solution with a syringe at -80 °C. After the drop, the resulting solution was stirred atroom temperature for 1 hour.After the stirring, this solution was cooled to -80 °C. Then, a solution in which 17 g (66 mmol) of iodine had been dissolved in 60 mL of tetrahydrofuran was dropped into this solution with a dripping funnel at -80 °C. After the drop, thissolution was stirred for 17 hours while its temperature was returned to room temperature. After the stirring, an aqueous solution of sodium thiosulfate was added to the resulting mixture, and the mixture was stirred for 1 hour. After the stirring, an organic layer of this mixture was washed with water and a saturated aqueous solution of sodium hydrogen carbonate, and then magnesium sulfate was added to the organic layer. The mixture was gravity-filtered to give a filtrate, and then the filtrate was concentratedto give a solid.The resulting solid was recrystallized from toluene/hexane to give a pale brown solid. Ethanol was added to the resulting solid, irradiation with ultrasonic waves was performed, and a solid was collected by suction filtration to give 11 g (31 mmol) of paleyellow powder of the target substance in 56 % yield. A synthesis scheme of Step 1 is shown in (a-i).
45% Stage #1: benzo[b]naphtho[1,2-d]furan With n-butyllithium In tetrahydrofuran; hexane at -75 - 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -75 - 20℃; for 17h; Inert atmosphere; 5.1-1 Synthesis of 6-Iodobenzo[6]naphtho[1,2-d]furan Into a 500 mL three-neck flask was put 8.5 g (39 mmol) of benzo[b]naphtho[1,2-d]furan, and the air in the flask was replaced with nitrogen. Then, 195 mL of tetrahydrofuran (THF) was added thereto. This solution was cooled to -75 °C. Then, 25 mL (40 mmol) of n-butyllithium (a 1.59 mol/L n-hexane solution) was dropped into this solution. After the drop, the resulting solution was stirred at room temperature for 1 hour. After the stirring, the resulting solution was cooled to -75 °C. Into this solution, a solution in which 10 g (40 mmol) of iodine was dissolved in 40 mL of THF was dropped. After the drop, the resulting solution was stirred for 17 hours while the temperature of the solution was returned to room temperature. After the stirring, an aqueous solution of sodium thiosulfate was added to the mixture, and the resulting mixture was stirred for 1 hour. Then, the organic layer of the mixture was washed with water and dried with magnesium sulfate. After the drying, the mixture was gravity-filtered to give a solution. The resulting solution was suction-filtered through Celite (Catalog No. 531-16855 produced by Wako Pure Chemical Industries, Ltd., the same applies to Celite described below and a repetitive description thereof is omitted) and Florisil (Catalog No. 540-00135 produced by Wako Pure Chemical Industries, Ltd., the same applies to Florisil described below and a repetitive description thereof is omitted) to give a filtrate. The resulting filtrate was concentrated to give a solid. The resulting solid was recrystallized from toluene to give 6.0 g (18 mmol) of white powder of the target substance in a yield of 45 %.
45% Stage #1: benzo[b]naphtho[1,2-d]furan With n-butyllithium In tetrahydrofuran; hexane at -75 - 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -75℃; for 17h; Stage #3: With sodium thiosulfate In tetrahydrofuran; hexane; water at 20℃; for 1h; 1.1 Step 1: Synthesis of 6-iodobenzo[b]naphtho[ 1 ,2-d]furan Into a 500 mL three-neck flask was put 8.5 g (39 mmol) of benzo[b]naphtho[1,2-d]furan, and the air in the flask was replaced with nitrogen. Then, 195 mL of tetrahydrofuran (THF) was added thereto. After this solution was cooled to -75 °C, 25 mL (40 mmol) of n-butyllithium (a 1.59 mol/L n-hexane solution) was dropped into this solution. After the dropping, the resulting solution was stirred at room temperature for 1 hour. After a predetermined period of time, the resulting solution was cooled to -75 °C. Then, a solution in which 10 g (40 mmol) of iodine had been dissolved in 40 mL of THF was dropped into this solution. After the dropping, the resulting solution was stirred for 17 hours while thetemperature of the solution was returned to room temperature. Next, an aqueous solution of sodium thiosulfate was added to the mixture, and the resulting mixture was stirred for 1 hour. Then, the organic layer of the mixture was washed with water and dried with magnesium sulfate. After the drying, the mixture was gravity-filtered to give a solution. The resulting solution was suction-filtered through Florisil (Catalog No. 066-05265 produced by Wako Pure ChemicalIndustries, Ltd.) and Celite (Catalog No. 537-02305 produced by Wako Pure Chemical Industries, Ltd.) to give a filtrate. The resulting filtrate was concentrated to give a solid. The resulting solid was recrystallized from toluene to give 6.0 g (18 mmol) of the target white powder in a yield of 45 %. A synthesis scheme (a-i) of Step 1 is shown below.
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