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[ CAS No. 3074-03-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 3074-03-1
Chemical Structure| 3074-03-1
Structure of 3074-03-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3074-03-1 ]

CAS No. :3074-03-1 MDL No. :MFCD00215960
Formula : C17H10O Boiling Point : -
Linear Structure Formula :- InChI Key :MLMNDNOSVOKYMT-UHFFFAOYSA-N
M.W : 230.26 Pubchem ID :18311
Synonyms :

Calculated chemistry of [ 3074-03-1 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.82
TPSA : 17.07 Ų

Pharmacokinetics

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) : -4.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 4.83
Log Po/w (WLOGP) : 4.05
Log Po/w (MLOGP) : 3.43
Log Po/w (SILICOS-IT) : 4.68
Consensus Log Po/w : 3.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.97
Solubility : 0.00248 mg/ml ; 0.0000108 mol/l
Class : Moderately soluble
Log S (Ali) : -4.92
Solubility : 0.00276 mg/ml ; 0.000012 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.76
Solubility : 0.0000402 mg/ml ; 0.000000175 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.17

Safety of [ 3074-03-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3074-03-1 ]

* 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 [ 3074-03-1 ]

[ 3074-03-1 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 3074-03-1 ]
  • [ 243-17-4 ]
YieldReaction ConditionsOperation in experiment
90% With lithium aluminium tetrahydride; aluminium trichloride Heating;
82% With iodine; acetic acid In water at 80℃; 1 [194] Preparation of compound 1-2 [195] 33.3 g of iodine (144 mmol), 44 g of hypophosphorous acid (660 mmol, 50% aqueous solution), and 2000 mL of acetic acid were introduced into a reaction vessel, and the mixture was stirred at 80°C for 30 minutes. 95 g of compound 1-1 (413 mmol) was slowly added dropwise thereto and the mixture was stirred under reflux overnight. The reaction solution was cooled to room temperature, and the separated solid was filtered and washed with cold methyl alcohol and hexane to obtain 73 g of compound 1-2 (yield: 82%).
82% With iodine; hypophosphorous acid; acetic acid In water Reflux; 1 Preparation of compound 1-2 33.3 g of iodine (144 mmol), 44 g of hypophosphorous acid (660 mmol, 50% aqueous solution), and 2000 mL of acetic acid were introduced into a reaction vessel, and the mixture was stirred at 80°C for 30 minutes. 95 g of compound1-1(413 mmol) was slowly added dropwise thereto and the mixture was stirred under reflux overnight. The reaction solution was cooled to room temperature, and the separated solid was filtered and washed with cold methyl alcohol and hexane to obtain 73 g of compound1-2(yield: 82%).
With zinc
With palladium on activated charcoal; ethanol Hydrogenation;
Multi-step reaction with 2 steps 1: 100 percent / 5percent Pd/C / 760 Torr 2: 5percent Pd/C / 760 Torr

  • 3
  • [ 243-17-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
99% With 2-Picolinic acid; sodium tetrahydroborate; bismuth(III) oxide In pyridine; water; acetic acid at 100℃; for 16h;
99% With oxygen In octane at 80℃; for 6h; Schlenk technique;
95% With air; graphene-supported KOH composite In N,N-dimethyl-formamide at 20℃; for 24h;
89% With oxygen In N,N-dimethyl acetamide at 130℃; for 3h; Schlenk technique;
86% With oxygen; sodium hexamethyldisilazane In tetrahydrofuran at 60℃; for 12h; Sealed tube; Green chemistry; 3.2. Representative Procedure for the Oxidation of Diarylmethane General procedure: To an 8 mL oven-dried vial, 4-benzylpyridine (0.1 mmol), dry THF (1 mL), LiHMDS (0.15mmol) were added subsequently. The reaction system was sealed by a rubber septum with a needleconnected with O2 balloon. After stirring at 60 °C for 12 h, the reaction mixture was passed througha short pad of silica gel and eluted with ethyl acetate (1 mL × 3). The combined organics wereconcentrated under reduced pressure. The residue was purified by flash chromatography to givethe diarylketone 2a as white solid (15.6 mg, 85% yield).
With sodium dichromate; acetic acid
With sodium dichromate; acetic acid
Irradiation;
bei der Oxydation;
With pyridine; tert.-butylhydroperoxide; acetic acid In water at 100℃; for 19.5h; 1 1) Catalytic oxidation of benzylic positions via redox activation of bismuth; General oxidation procedure 1; To a suspension of bismuth oxide (37 mg, 10 mol%), in distilled water (1.5 rnL), stirred at room temperature in a microwave vessel, was added sodium borohydride (18 mg, 60 mol%). An exothermic reaction was observed, with formation of a finely divided, black precipitate of bismuth metal. Washing with water (2x2 mL), removal of the supernatant afforded activated Bi(O). After addition of pyridine (0.8 mL), acetic acid (0.08 mL), picolinic acid (20 mg, 20 mol%), substrate (0.8 mmol) and -butyl hydroperoxide (70% in water, 0.66 mL, 6 eq), the vessel was sealed, the mixture sonicated for 30 min, and gradually heated to the indicated temperature, then stirred for the indicated period of time. After completion of the heating period, cooling to EPO room temperature, diluting with diethyl ether, filtration over Celite, afforded a crude sample, which was analyzed by GCMS.

  • 4
  • [ 18508-00-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
With lead(II) oxide at 260 - 270℃;
  • 6
  • [ 55270-95-6 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride Diazotization;
  • 7
  • 11-oxo-11<i>H</i>-benzo[<i>b</i>]fluorene-5-carboxylic acid [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
With quinoline; copper oxide-chromium oxide
  • 8
  • [ 83-33-0 ]
  • [ 643-79-8 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
55% With sodium ethanolate In ethanol for 2h; Reflux; 1 [192] Preparation of compound 1-1 [193] 100 g of indanone (757 mmol), 111.6 g of phthalaldehyde (832 mmol), 10.3 g of 20% sodium ethoxide ethyl alcohol solution (151 mmol), and 1300 mL of ethyl alcohol were introduced into a reaction vessel. After the mixture was refluxed for 2 hours, the mixture was cooled to room temperature and stirred overnight. The reaction solution was cooled to 0°C, and the separated solid was filtered and washed with cold methyl alcohol and hexane to obtain 95 g of compound 1-1 (yield: 55%).
55% With sodium ethanolate In ethanol for 2h; Reflux; 1 Preparation of compound 1-1 100 g of indanone (757 mmol), 111.6 g of phthalaldehyde (832 mmol), 10.3 g of 20% sodium ethoxide ethyl alcohol solution (151 mmol), and 1300 mL of ethyl alcohol were introduced into a reaction vessel. After the mixture was refluxed for 2 hours, the mixture was cooled to room temperature and stirred overnight. The reaction solution was cooled to 0°C, and the separated solid was filtered and washed with cold methyl alcohol and hexane to obtain 95 g of compound1-1(yield: 55%).
50.2% With sodium ethanolate In ethanol 1.) overnight, 2.) reflux, 24 h;
41% Stage #1: inden-1-one; o-phthalic dicarboxaldehyde In methanol for 0.5h; Stage #2: With potassium hydroxide In methanol for 3h; Reflux;
With methanol; potassium hydroxide
With potassium hydroxide; ethanol

  • 9
  • [ 3074-03-1 ]
  • [ 5693-33-4 ]
  • 3-(naphthalen-2-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 2.32 g 2: 45% With potassium hydroxide In toluene for 4h; Heating;
  • 11
  • [ 328086-35-7 ]
  • [ 3074-03-1 ]
  • 5-(trimethylsilyl)benzo[b]fluoren-11-one [ No CAS ]
  • 6-(trimethylsilyl)benzo[a]fluorene-11-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 18% 3: 11% With crithmene In toluene at 180℃; for 79h;
1: 37% 2: 11% 3: 18% With crithmene In toluene at 180℃; for 79h;
1: 24% 2: 20% 3: 32% at 180℃; for 14h; solid state, celite;
1: 25% 2: 18% 3: 8% In 1,2-dichloro-benzene at 180℃; for 96h;

  • 12
  • [ 251-41-2 ]
  • [ 3074-03-1 ]
  • [ 328563-84-4 ]
YieldReaction ConditionsOperation in experiment
81%
  • 13
  • [ 3074-03-1 ]
  • [ 405290-76-8 ]
YieldReaction ConditionsOperation in experiment
90% With hydrazine hydrate In ethanol for 9h; Heating;
  • 14
  • [ 280763-58-8 ]
  • [ 3074-03-1 ]
  • 6-trimethylsilanyl-benzo[<i>c</i>]fluoren-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 61% With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.0833333h;
1: 59% 2: 23% Stage #1: 1-[2-(2-phenyl-1-ethynyl)phenyl]-3-(trimethylsilyl)-2-propyn-1-one In toluene at 150℃; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran
  • 15
  • C23H16IN [ No CAS ]
  • [ 479-79-8 ]
  • [ 3074-03-1 ]
  • 16
  • methyl 11-methoxy-11H-benzo[b]fluorene-11-carboxylate [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
With chromium(VI) oxide In water; acetic acid for 0.75h; Heating;
  • 17
  • [ 77123-58-1 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / n-BuLi / tetrahydrofuran; hexane / 5 h / 0 - 23 °C 2: 91 percent / BaMnO4 / CH2Cl2 / 72 h / 23 °C 3: 32 percent / 14 h / 180 °C / solid state, celite
  • 18
  • [ 328086-30-2 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / BaMnO4 / CH2Cl2 / 72 h / 23 °C 2: 32 percent / 14 h / 180 °C / solid state, celite
Multi-step reaction with 2 steps 1: 91 percent / BaMnO4 / CH2Cl2 / 3 h / 20 °C 2: 37 percent / γ-terpinene / toluene / 79 h / 180 °C
  • 19
  • [ 3074-03-1 ]
  • 11-methyl-11H-benzo[b]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4.98 g / diethyl ether / 32 h 2: 0.98 g / HI / acetic acid / Heating
  • 20
  • [ 59046-72-9 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: 0.25 h 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 61 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: 0.25 h 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. borax / methanol / 20 °C 4.1: 70 percent / benzene / 150 °C
  • 21
  • [ 536-74-3 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: 0.25 h 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 61 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C
Multi-step reaction with 5 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: 0.25 h 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. borax / methanol / 20 °C 4.1: 70 percent / benzene / 150 °C
  • 22
  • [ 879286-37-0 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: MnO2 / CH2Cl2 / 20 °C 2: 61 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C
Multi-step reaction with 3 steps 1: MnO2 / CH2Cl2 / 20 °C 2: aq. borax / methanol / 20 °C 3: 70 percent / benzene / 150 °C
Multi-step reaction with 3 steps 1: 94 percent / PCC / CH2Cl2 / 4 h / 20 °C 2: 85 percent / aq. borax / methanol / 0.5 h / 20 °C 3: 74 percent / toluene / 13 h / 150 °C
  • 23
  • [ 280763-58-8 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. borax / methanol / 20 °C 2: 70 percent / benzene / 150 °C
Multi-step reaction with 2 steps 1: 85 percent / aq. borax / methanol / 0.5 h / 20 °C 2: 74 percent / toluene / 13 h / 150 °C
  • 24
  • [ 3074-03-1 ]
  • [ 96615-37-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C
  • 25
  • [ 3074-03-1 ]
  • [ 405290-75-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C 3: 58 percent / benzene / 4 h / Heating
  • 26
  • [ 3074-03-1 ]
  • 9-(11'H-benzo[b]fluoren-11'-ylidene)-9H-thioxanthene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C 3: 58 percent / benzene / 4 h / Heating 4: 97 percent / PPh3 / benzene / 8 h / Heating
  • 27
  • [ 3074-03-1 ]
  • [ 405290-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C 3: 58 percent / benzene / 3 h / Heating
  • 28
  • [ 3074-03-1 ]
  • 9-(11'H-benzo[b]fluoren-11'-ylidene)-9H-telluroxanthene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C 3: 58 percent / benzene / 3 h / Heating 4: 65 percent / PPh3 / benzene / 25 h / Heating
  • 29
  • [ 3074-03-1 ]
  • [ 405290-73-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C 3: 65 percent / benzene / 7 h / Heating
  • 30
  • [ 3074-03-1 ]
  • 9-(11'H-benzo[b]fluoren-11'-ylidene)-9H-selenoxanthene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 90 percent / NH2NH2*H2O / ethanol / 9 h / Heating 2: 87 percent / HgO; Na2SO4; KOH / diethyl ether; ethanol / 5 h / 20 °C 3: 65 percent / benzene / 7 h / Heating 4: 75 percent / PPh3 / benzene / 3 h / Heating
  • 31
  • [ 3074-03-1 ]
  • [ 98677-74-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether / 1 h / Ambient temperature 2: p-TsOH / hexane
  • 32
  • [ 3074-03-1 ]
  • [ 98677-86-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether / 1 h / Ambient temperature 2: p-TsOH / hexane
  • 33
  • [ 3074-03-1 ]
  • [ 131544-01-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.73 g / tetrahydrofuran / 16 h 2: HI / acetic acid / 1 h / 80 °C
  • 34
  • [ 3074-03-1 ]
  • [ 88746-48-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium/charcoal; ethanol / Hydrogenation 2: trityl sodium; diethyl ether / Herstellung von 11<i>H</i>-Benzo<<i>b</i>>fluoren-11-<14<i>C</i>>carbonsaeure; anschliessend Behandeln mit 14CO2
  • 35
  • [ 4859-45-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: concentrated H2SO4 2: copper oxide-chromium oxide; quinoline
  • 36
  • [ 156753-34-3 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: aqueous HCl / Diazotization
  • 37
  • phenylmagnesium bromide [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: benzene; diethyl ether / 0 °C 3: aqueous HCl / Diazotization
  • 38
  • [ 1221067-88-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
84% With sulfuric acid In 1,2-dichloro-ethane for 4h; Reflux;
  • 40
  • C18H13NO [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water at 100℃; Inert atmosphere;
  • 41
  • [ 644-13-3 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
79% With palladium diacetate; silver(l) oxide In trifluoroacetic acid at 130℃; for 36h; Inert atmosphere;
50% With trifluoroacetic acid; silver(l) oxide In water at 130℃; for 22h; chemoselective reaction;
48% With palladium diacetate; potassium carbonate; trifluoroacetic acid; silver(l) oxide at 140℃; for 24h; Schlenk technique; Inert atmosphere;
  • 42
  • [ 580-13-2 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 2 h / 20 - 85 °C 1.2: 0 - 20 °C / Inert atmosphere 2.1: pyridinium chlorochromate; triethylamine / dichloromethane / 20 °C 3.1: palladium diacetate; trifluoroacetic acid; potassium carbonate; silver(l) oxide / 24 h / 140 °C / Schlenk technique; Inert atmosphere
  • 43
  • [ 100-52-7 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 2 h / 20 - 85 °C 1.2: 0 - 20 °C / Inert atmosphere 2.1: pyridinium chlorochromate; triethylamine / dichloromethane / 20 °C 3.1: palladium diacetate; trifluoroacetic acid; potassium carbonate; silver(l) oxide / 24 h / 140 °C / Schlenk technique; Inert atmosphere
  • 44
  • [ 35060-38-9 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridinium chlorochromate; triethylamine / dichloromethane / 20 °C 2: palladium diacetate; trifluoroacetic acid; potassium carbonate; silver(l) oxide / 24 h / 140 °C / Schlenk technique; Inert atmosphere
  • 45
  • [ 3815-22-3 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: silver hexafluoroantimonate; [RhCl2(p-cymene)]2; silver(l) oxide / tetrahydrofuran / 16 h / 110 °C / Inert atmosphere 2.1: trifluoroacetic anhydride / 2 h / 100 °C 2.2: 2 h / 100 °C
  • 46
  • [ 1402849-74-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-methyl-3-phenyl-2-naphthamide With trifluoroacetic anhydride at 100℃; for 2h; Stage #2: With hydrogenchloride In water at 100℃; for 2h;
  • 47
  • [ 3074-03-1 ]
  • [ 5693-33-4 ]
YieldReaction ConditionsOperation in experiment
42% With potassium hydroxide In toluene for 4h; Reflux;
  • 48
  • [ 3074-03-1 ]
  • [ 479-79-8 ]
  • 49
  • [ 3074-03-1 ]
  • [ 1353012-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / toluene / 4 h / Reflux 2: PPA / 4 h / 75 °C / Inert atmosphere 3: Lawessons reagent / benzene / 5 h / Reflux
  • 50
  • [ 3074-03-1 ]
  • [ 1448168-83-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hydroxide / toluene / 4 h / Reflux 2: PPA / 4 h / 75 °C / Inert atmosphere 3: Lawessons reagent / benzene / 5 h / Reflux 4: hydrazine hydrate / benzene; ethanol / 2 h / Reflux
  • 51
  • [ 3074-03-1 ]
  • [ 841-75-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium hydroxide / toluene / 4 h / Reflux 2: PPA / 4 h / 75 °C / Inert atmosphere 3: Lawessons reagent / benzene / 5 h / Reflux 4: hydrazine hydrate / benzene; ethanol / 2 h / Reflux 5: potassium hydroxide; mercury(II) oxide; sodium sulfate / ethanol; diethyl ether / 3 h / 0 °C
  • 52
  • [ 3074-03-1 ]
  • (E)-11-(11H-benzo[a]fluorene-11-ylidene)-11H-benzo[a]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hydroxide / toluene / 4 h / Reflux 2: PPA / 4 h / 75 °C / Inert atmosphere 3: Lawessons reagent / benzene / 5 h / Reflux 4: toluene / 12 h / 100 °C
Multi-step reaction with 6 steps 1: potassium hydroxide / toluene / 4 h / Reflux 2: PPA / 4 h / 75 °C / Inert atmosphere 3: Lawessons reagent / benzene / 5 h / Reflux 4: hydrazine hydrate / benzene; ethanol / 2 h / Reflux 5: potassium hydroxide; mercury(II) oxide; sodium sulfate / ethanol; diethyl ether / 3 h / 0 °C 6: toluene / 12 h / 100 °C
  • 53
  • [ 66252-13-9 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: [bis(pyridine)iodine]+ tetrafluoroborate; tetrafluoroboric acid / dichloromethane; diethyl ether / 24 h / -70 °C 2: palladium diacetate; triphenylphosphine; triethylamine / water; N,N-dimethyl-formamide / 22 h / 130 °C / Inert atmosphere
  • 54
  • [ 32316-92-0 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; potassium carbonate / water; N,N-dimethyl-formamide / 2 h / 20 °C 2: [bis(pyridine)iodine]+ tetrafluoroborate; tetrafluoroboric acid / dichloromethane; diethyl ether / 24 h / -70 °C 3: palladium diacetate; triphenylphosphine; triethylamine / water; N,N-dimethyl-formamide / 22 h / 130 °C / Inert atmosphere
  • 55
  • 2-(3-iodonaphthalen-2-yl)benzonitrile [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
66% With palladium diacetate; triethylamine; triphenylphosphine In water; N,N-dimethyl-formamide at 130℃; for 22h; Inert atmosphere;
  • 56
  • [ 2042-37-7 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; potassium carbonate / water; N,N-dimethyl-formamide / 2 h / 20 °C 2: [bis(pyridine)iodine]+ tetrafluoroborate; tetrafluoroboric acid / dichloromethane; diethyl ether / 24 h / -70 °C 3: palladium diacetate; triphenylphosphine; triethylamine / water; N,N-dimethyl-formamide / 22 h / 130 °C / Inert atmosphere
  • 57
  • [ 3074-03-1 ]
  • [ 92-86-4 ]
  • C46H30O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.2% Stage #1: 4-(4-bromophenyl)bromobenzene With magnesium; lithium chloride In tetrahydrofuran; ethylene dibromide for 9h; Inert atmosphere; Reflux; Stage #2: 11H-Benzo[b]fluoren-11-one In tetrahydrofuran; ethylene dibromide at 50℃; for 5.5h; Reflux; 4 Synthesis Example 4 Synthesis of Biphenyl Derivative (12) Synthesis Example 4 Synthesis of Biphenyl Derivative (12) In a nitrogen atmosphere, 24.3 g (1.00 mol) of magnesium was weighed and fed into a 5-L four-neck flask, to which a portion of a solution of 156 g (0.50 mol) of 4,4′-dibromobiphenyl and 22.5 g (0.53 mol) of lithium chloride in 1,000 ml of dry THF was added until the magnesium was immersed therein. An amount of dibromoethane was added whereupon reaction started. The remaining portion of the THF solution was added dropwise over 5 hours while maintaining the exothermic reaction. At the end of dropwise addition, 500 ml of THF was added to the reaction solution, which was ripened for 4 hours under reflux to form a Grignard reagent. The flask was cooled to an internal temperature of 50° C., a suspension of 177.3 g (0.77 mol) of 9-benzo[b]fluorenone in 1,500 ml of dry THF was added dropwise over 30 minutes. At the end of dropwise addition, the solution was ripened for 5 hours under reflux. The flask was cooled in an ice bath, whereupon 1,000 ml of saturated ammonium chloride aqueous solution was added to quench the reaction. The reaction solution was combined with 500 ml of MIBK and transferred to a separatory funnel, from which the water layer was discharged. After further separatory washing with 500 ml of deionized water and saturated saline, the organic layer was dried over magnesium sulfate. After filtration of the drying agent and distillation of the solvent, the residue was purified by column chromatography, obtaining 53.2 g (yield 21.1%) of biphenyl derivative (12). Biphenyl Derivative (12): (0165) IR (KBr): ν=3543, 3427, 3050, 1637, 1607, 1504, 1494, 1251, 1168, 1038, 882, 817, 781, 755 cm-1 (0166) 1H-NMR (600 MHz in DMSO-d6): δ=6.49 (2H, -OH, s), 7.29-7.32 (8H, m), 7.41-7.48 (10H, m), 7.75 (2H, s), 7.86 (2H, d), 7.95 (2H, d), 7.97 (2H, d), 8.31 (2H, d) ppm (0167) 13C-NMR (150 MHz in DMSO-d6): δ=82.03, 118.21, 120.72, 123.52, 125.05, 125.75, 125.83, 126.22, 126.31, 128.03, 128.33, 128.84, 128.87, 133.35, 133.64, 137.85, 138.40, 138.59, 144.90, 149.64, 151.07 ppm
  • 58
  • 2-(naphthalen-2’-yl)benzaldehyde [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium sulfate / dichloromethane / 5 h / 20 °C 2.1: [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 24 h / 80 °C 2.2: 2 h / 20 °C
  • 59
  • C24H19N [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: C24H19N With [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 80℃; for 24h; Stage #2: With hydrogenchloride In 1,2-dichloro-ethane at 20℃; for 2h;
  • 60
  • [ 3074-03-1 ]
  • C41H28BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C 2: Eaton′s Reagent / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 61
  • [ 3074-03-1 ]
  • C51H35N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C 2: Eaton′s Reagent / dichloromethane / 2 h / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol / 3 h / 120 °C
  • 62
  • [ 3074-03-1 ]
  • [ 100-58-3 ]
  • 11-hydroxy-11-phenyl-11H-benzo<b>fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; 3 Preparation of compound 3-1[176]After introducing 11H-benzo[b]fluoren-11-one (41.5g, 181 mmol), and tetrahydrofuran 550mL into a reaction vessel, the reaction mixture was cooled to 0°C, and then phenyl magnesium bromide (78mL, 235mmol, 3M diethylether solution) was slowly added dropwise thereto. The reaction mixture was stirred at room temperature for 1 hour. After adding ammonium chloride aqueous solution to the reaction mixture to terminate the reaction, the mixture was diluted with ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, distilled under reduced pressure, and purified by column chromatography to obtain compound 3-1 (56 g, 99%).
  • 63
  • [ 132-64-9 ]
  • [ 3074-03-1 ]
  • C29H18O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 11H-Benzo[b]fluoren-11-one In tetrahydrofuran at -78 - 20℃; 5 Preparation of compound 5-1[190]After introducing dibenzofuran (21g, 127mmol) and tetrahydrofuran 330mL into a reaction vessel, the mixture was subjected into nitrogen atmosphere, and cooled to -78°C. After slowly adding n-butyl lithium (50mL, 2.5 M, 115mmol) dropwise, the mixture was stirred at -78°C for 2 hours. After slowly adding 11H-benzo[B]fluorene-11-one (26g, 115mmol) dissolved in tetrahydrofuran 330mL dropwise, the mixture was slowly warmed to room temperature, and stirred overnight. After adding ammonium chloride aqueous solution to the reaction mixture to terminate the reaction, the mixture was extracted with methylene chloride (MC). The extracted organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The products were purified by column chromatography to obtain compound 5-1 (44g, 96%).
  • 64
  • 7,12-dihydro-1-oxoindeno[3,2-c][2]benzooxepine [ No CAS ]
  • [ 3074-03-1 ]
  • [ 15875-52-2 ]
YieldReaction ConditionsOperation in experiment
1: 8% 2: 82% With caesium carbonate In ethanol at 80℃; for 2h; General procedure for the synthesis of 2 (2a as an example). General procedure: A mixture of 6H-benzo[e]indeno[1,2-b]oxepin-12(11H)-one 1a (248 mg, 1.0 mmol), and Cs2CO3 (652 mg, 2 mmol) in EtOH (5 mL) was stirred at 80 C for 2 h. The resulting mixture was then poured into 300 mL 1 M HCl (aq) and extracted with EtOAc 3 times (3x100 mL). The organic extract was dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc 20/1) to afford the products 2a.
  • 65
  • [ 3074-03-1 ]
  • 1-(11H-benzo[b]fluoren-11-yl)-3-(2,6-dihydroxybenzoyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride / ethanol; water / 3 h / Reflux 2: zinc; acetic acid / water / 1 h / 110 °C 3: triethylamine / 1,2-dichloro-ethane / Reflux 4: acetone / 10 h / 110 °C 5: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 4 h / 40 °C
  • 66
  • [ 3074-03-1 ]
  • C39H30N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / ethanol; water / 3 h / Reflux 2: zinc; acetic acid / water / 1 h / 110 °C 3: triethylamine / 1,2-dichloro-ethane / Reflux 4: acetone / 10 h / 110 °C
  • 67
  • [ 3074-03-1 ]
  • 2,3-benzofluorenone oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride In ethanol; water for 3h; Reflux; 9H-Fluoren-9-one oxime (26a) General procedure: A mixture of hydroxylamine hydrochloride (5.0 g) and 9H-fluoren-9-one (27a, 5.0 g) in 70% alcohol (50 mL) was refluxed under stirring for 3 h, poured into H2O (100 mL), filtered, washed, and dried, to afford 26a (4.9 g, 90%) as yellow solid: mp 195-196 °C (lit.4 192-194°C); 1H NMR (400 MHz, DMSO-d6) δ: 12.56 (s, 1H), 8.35 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.5 Hz, 1H), 7.84 (t, J = 7.4 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 7.51 (t,J = 7.5 Hz, 1H), 7.44 (t, J = 7.5 Hz, 1H), 7.39 (t, J =7.6 Hz, 1H), 7.34 (t, J = 7.5 Hz, 1H); EI-MS m/z 195.1 (M+), 179.1 (100%).
  • 68
  • [ 71-43-2 ]
  • [ 93-09-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
53% With sodium persulfate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; trifluorormethanesulfonic acid; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique;
  • 69
  • [ 32316-92-0 ]
  • [ 98-88-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
72% With C31H25N2O3PPdS; potassium hydroxide In methanol; water at 50℃; for 7h; Green chemistry; regioselective reaction;
  • 70
  • [ 3074-03-1 ]
  • [ 100-59-4 ]
  • 11-hydroxy-11-phenyl-11H-benzo<b>fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.6 g In tetrahydrofuran at 0 - 20℃; for 8h; 4 Synthesis of 4-(11-phenyl-11H-benzo[b]fluorene-11-yl)phenol 11H-benzo [b]fluorene-11-one (23.0 g) was added to tetrahydrofuran solvent (200 ml), and the reaction mixture was cooled to 0° C. 2M phenyl magnesium chloride tetrahydrofuran solution (60 mL) was slowly added thereto. After the addition was completed, the reaction mixture was raised to room temperature, and stirred for an additional 8 hours. After the reaction was completed, a saturated ammonium chloride aqueous solution (200 ml) was slowly added to the reaction solution, and ethyl acetate (200 ml) was added thereto, thereby performing an extraction process. A water layer was subjected to additional extraction with ethyl acetate (200 ml). Water in an oil layer was removed with anhydrous sodium sulfate, and filtered. The organic solvent was removed by distillation under reduced pressure, and high purity of 11-phenyl-11H-benzo[b]fluorene-11-ol (22.6 g) was obtained by purification using silica gel column chromatography. Phenol (68 g) and sulfuric acid (2.0 ml) were added to a dichloromethane solvent (100 ml). 11-phenyl-11H-benzo[b]fluorene-11-ol (22.6 g) was added thereto at room temperature, followed by stirring for 1 hour to perform the reaction. After the reaction, an organic layer was washed with water once and 1N sodium hydroxide aqueous solution twice. An organic solvent was removed by distillation under reduced pressure, and high purity of 4-(11-phenyl-11H-benzo[b]fluorene-11-yl)phenol (13.0 g) was secured through toluene recrystallization. (0151) 1H NMR (CDCl3, 500 MHz) δ 8.22 (s, 1H), 8.04-7.88 (m, 4H), 7.86 (d, 1H), 7.53-7.35 (m, 4H), 7.27 (m, 5H), 7.10 (d, 2H), 6.70 (d, 2H), 4.63 (s, 1H)
  • 71
  • (E)-3-phenyl-1-(2'-trimethylsilylethynyl)phenyl-2-enoacetone [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
69% With copper(l) iodide; Selectfluor In dimethyl sulfoxide at 65℃; for 3h; 10 Example 10 A mixture of 0.3 mmol of (E) -3-phenyl-1- (2'-trimethylsilylethynyl) phenyl-2-enoacetone (91.2 mg), 0.6 mmol of Selectfluor (212.4 mg) and 0.03 mmol of CuI 5.97 mg) was added to a 15 mL thick-walled pressure-resistant reaction tube, and 3 mL of DMSO was added as a solvent. Then, the mixture was magnetically stirred at 65 ° C for 3 hours. Then, silica gel (100-200 mesh) was added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography using petroleum ether / ethyl acetate = 30: 1 as the eluent The eluate containing the product was collected and the eluent was evaporated to give 11H-benzofluorenone. The material was a yellow solid in 69% yield.
  • 72
  • [ 3074-03-1 ]
  • [ 108-95-2 ]
  • 11,11-bis(4-hydroxyphenyl)-11H-benzo[b]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With methanesulfonic acid; 3-mercaptopropionic acid at 40 - 60℃; for 1.5h; 4 24.0 g of 2,3-benzofluorenone and 49.1 g of phenol were weighed out in a three-necked flask equipped with a stirrer, a condenser and a thermometer, and 20 ml of dimethyl carbonate was added and dissolved at 40 ° C. 0.4 g of 3-mercaptopropionic acid was added to the solution in the three-necked flask, 13.5 g of methanesulfonic acid was added dropwise over 30 minutes, and the mixture was stirred at 60 ° C. for 1 hour, whereupon white crystals precipitated . After cooling the solution in the three-necked flask to room temperature, 300 ml of toluene was added and stirred for 1 hour, and white crystals were separated by filtration. And dried in a vacuum oven to obtain 38.4 g of white crystals (yield 92%, HPLC (High Performance Liquid Chromatography) purity 98.2%).
  • 73
  • [ 3074-03-1 ]
  • C67H40BrN3 [ No CAS ]
  • C84H49N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: C67H40BrN3 With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 11H-Benzo[b]fluoren-11-one In tetrahydrofuran at -78 - 28℃; for 12h; Stage #3: In acetic anhydride at 120℃; for 5h; Reflux; 4 Synthesis of compound 63 The test apparatus was sufficiently dried,A 2 L three-necked flask was charged with 37.5 g (38.8 mml, 1.1 eq.)Of intermediate-31, 700 ml of dry tetrahydrofuran was added,After dissolution, the temperature was lowered to -78 ° C and 16.9 ml of 2.5 M (42.2 mmol, 1.2 eq.) Of n-BuLi was added dropwise.After completion of the dropwise addition, the mixture was stirred at that temperature for 1 hour,8.1 g (35.2 mmol, 1.0 eq.) Of 11H-benzo [B] fluorene-11-one was added dropwise at this temperature,After completion of the dropwise addition, the mixture was stirred at room temperature for 12 hours.To end the reaction,Add 4M hydrochloric acid solution,Extracted with methylene chloride, the organic phase was washed with saturated brine to neutral, dried, the solvent was removed, dried sufficiently, and then fed to a 2 L dry three-necked flask,400 ml of acetic anhydride was added, the temperature was raised to 120 ° C, and the mixture was refluxed for 5 hours to complete the reaction. Cooled to room temperature,Remove the solvent, dissolve with methylene chloride, add the appropriate amount of water 3 times, dry, remove the solvent, dry, with toluene and ethanol to recrystallize,To give 26.7 g of compound 63 in a yield of 69%
  • 74
  • [ 68376-11-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C / Inert atmosphere; Schlenk technique 2: trifluorormethanesulfonic acid / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere; Schlenk technique
  • 75
  • [ 3074-03-1 ]
  • [ 7501-02-2 ]
  • C45H36O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In toluene at 50℃; for 2h; 1 A synthesis of a 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]-2,3-benzofluorene (9,9 -bis [4-(2-hydroxyethoxy)-3-phenylphenyl]benzo[b]fluorene, BOPPEBF) 11.6g (50mmol) of 2,3-benzo fluorenones (a benzo [b] fluorenone) and 53.6 g (250mmol) of 2-(o-phenylphenoxy) ethanol were dissolved in 40 g of toluene at 50 degrees C. The sulfuric acid 21.5g (215mmol) was added to the solution, and it stirred at the temperature of 50 degrees C for 2 hours. It dissolved in methyl isobutyl ketone and the reaction mixture was rinsed, after concentrating an organic layer in vacuum, the crude crystal produced by recrystallizing with toluene was reprecipitated with methanol, and the solid was obtained. When1H-NMR analyzed the obtained solid, it checked that it was a 9,9 -bis [4-(2-hydroxy ethoxy)-3-phenylphenyl]-2,3-benzofluorene. The purity of the solid measured by HPLC was 90.7%
  • 76
  • [ 3074-03-1 ]
  • [ 90-43-7 ]
  • C41H28O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; 3-mercaptopropionic acid In toluene at 50℃; for 4h; 2 A synthesis of a 9,9 -bis[4-(2-hydroxy)-3-phenylphenyl]-2,3-benzofluorene ( 9,9 -bis [4-(2-hydroxy)-3-phenylphenyl] 2,3-benzo[b]fluorene, BOPPBF) 23.2 g (100mmol) of 2,3-benzo fluorenones (a benzo [b] fluorenone), the o-phenylphenol 85.2g (500mmol), and 1.6 g of beta-mercaptopropionic acid were dissolved in 80 g of toluene at 50 degrees C. The sulfuric acid 51.6g was added to the solution, and it stirred at the temperature of 50 degrees C for 4 hours. The reaction mixture was dissolved in methyl isobutyl ketone, and the organic layer was rinsed. The solid was deposited by cooling an organic layer after rinsing, and it washed with methanol, and obtained the solid. When1H-NMR analyzed the obtained solid, it checked that it was a 9,9 -bis [4-hydroxy-3-phenylphenyl]-2,3-benzofluorene. The purity of the solid measured by HPLC was 99.5%
  • 77
  • [ 3074-03-1 ]
  • C50H39N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 80 °C
Multi-step reaction with 4 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 80 °C
  • 78
  • [ 3074-03-1 ]
  • C53H43N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 16 h / 80 °C
Multi-step reaction with 4 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 16 h / 80 °C
  • 79
  • [ 3074-03-1 ]
  • C52H41N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 80 °C
Multi-step reaction with 4 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / 80 °C
  • 80
  • [ 3074-03-1 ]
  • C58H45N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; toluene / 18 h / 80 °C
Multi-step reaction with 4 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; toluene / 18 h / 80 °C
  • 81
  • [ 3074-03-1 ]
  • 11,11-dimethyl-11H-benzo[b]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C
Multi-step reaction with 2 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C
  • 82
  • [ 3074-03-1 ]
  • C19H15Br [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C
  • 83
  • [ 3074-03-1 ]
  • C46H37N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodine; acetic acid / water / 80 °C 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / Reflux
Multi-step reaction with 4 steps 1.1: acetic acid; iodine; hypophosphorous acid / water / Reflux 2.1: potassium hydroxide; potassium iodide; N-benzyl-N,N,N-triethylammonium chloride / water; dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 20 °C 3.1: bromine / dichloromethane / 2 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 3 h / Reflux
  • 84
  • [ 1864-94-4 ]
  • [ 97295-35-7 ]
  • [ 479-79-8 ]
  • [ 3074-03-1 ]
  • 85
  • [ 583-55-1 ]
  • [ 66-99-9 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
70% With palladium diacetate; potassium hydrogencarbonate; DL-Pro-NHMe In tert-Amyl alcohol at 120℃; for 24h; Inert atmosphere; 10 4.2. General procedure for the synthesis of 9-fluorenone General procedure: A mixture of arylaldehyde (0.1 g, 1 mmol), dihaloarene (0.565 g, 2 mmol), Pd(OAc)2 (0.022 g, 10.0 mol%), N-phenylpicolinamide (L7, 0.019 g, 15.0 mol%) and potassium hydrogen carbonate (0.5 g, 5 mmol) in tert-amyl alcohol (5.0 ml) was taken in 100.0 ml round bottom flask under N2 atmosphere and stirred for 120°C for 24 h. Progress of the reaction was monitored continuously by TLC with ethyl acetate: hexane (2:3) eluent system. After completion of reaction, crude was poured into crushed ice and then filter the reaction mixture. Filtrate then extracted with ethyl acetate (3 times). Organic layer was separated, dried (over anhydrous Na2SO4) and evaporated under reduced pressure and purified by column chromatography to obtain desired product. Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found exactly similar as reported in the literature (References of above compound are mentioned in Supplementary data).
  • 86
  • 3-phenyl-N-tosyl-2-naphthamide [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
40% With trifluorormethanesulfonic acid; acetic acid at 130℃; for 1h;
  • 87
  • [ 93-09-4 ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride; magnesium sulfate / 1,2-dichloro-benzene / 24 h / 120 °C / Inert atmosphere 2: silver(l) oxide; potassium carbonate; palladium diacetate; acetic acid / 24 h / 130 °C / Inert atmosphere 3: trifluorormethanesulfonic acid; acetic acid / 1 h / 130 °C
  • 88
  • N′-methyl-N′-(pyridin-2-yl)benzohydrazide [ No CAS ]
  • [ 3074-03-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: cobalt(II) acetate; oxygen; potassium carbonate / 2,2,2-trifluoroethanol / 36 h / 140 °C / 760.05 Torr / Sealed tube; Inert atmosphere 2: cobalt(II) acetate; caesium carbonate; oxygen / 2,2,2-trifluoroethanol / 36 h / 140 °C / 760.05 Torr / Sealed tube; Inert atmosphere
Multi-step reaction with 2 steps 1: cobalt(II) acetate; oxygen; potassium carbonate / 2,2,2-trifluoroethanol / 36 h / 140 °C / 760.05 Torr / Sealed tube; Inert atmosphere 2: cobalt(II) acetate; caesium carbonate; oxygen / 2,2,2-trifluoroethanol / 36 h / 140 °C / 760.05 Torr / Sealed tube; Inert atmosphere
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