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Product Details of [ 103286-27-7 ]

CAS No. :103286-27-7 MDL No. :MFCD08061386
Formula : C9H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :WQUTYGRAHPHFBE-UHFFFAOYSA-N
M.W :213.07 Pubchem ID :11287326
Synonyms :

Calculated chemistry of [ 103286-27-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.3
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 2.66
Log Po/w (WLOGP) : 2.96
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.3
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.143 mg/ml ; 0.000669 mol/l
Class : Soluble
Log S (Ali) : -2.67
Solubility : 0.456 mg/ml ; 0.00214 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.98
Solubility : 0.0224 mg/ml ; 0.000105 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 103286-27-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 103286-27-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 103286-27-7 ]

[ 103286-27-7 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 74-93-1 ]
  • [ 103286-27-7 ]
  • [ 24852-84-4 ]
YieldReaction ConditionsOperation in experiment
85% With lithium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.5h;
  • 2
  • [ 103286-27-7 ]
  • [ 134365-29-0 ]
YieldReaction ConditionsOperation in experiment
92% With sulfuric acid; nitric acid for 2h;
  • 3
  • [ 103286-27-7 ]
  • [ 122-00-9 ]
YieldReaction ConditionsOperation in experiment
90% With sodium iodide; tin(ll) chloride In tetrahydrofuran; water for 2h; Heating;
  • 4
  • [ 591-17-3 ]
  • [ 75-36-5 ]
  • [ 103286-27-7 ]
  • [ 65095-33-2 ]
YieldReaction ConditionsOperation in experiment
53.8% With aluminium trichloride In dichloromethane Ambient temperature;
  • 5
  • [ 103286-27-7 ]
  • [ 100-52-7 ]
  • [ 874651-69-1 ]
YieldReaction ConditionsOperation in experiment
95% With sodium methylate In methanol at 0 - 20℃;
With sodium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere; Glovebox; Schlenk technique; enantioselective reaction;
  • 6
  • 4-methoxy-1-trimethylsilanyl-hepta-1,6-diyn-3-ol [ No CAS ]
  • [ 103286-27-7 ]
  • 1-[2-(5-hydroxy-4-methoxy-7-trimethylsilanyl-hepta-1,6-diynyl)-4-methyl-phenyl]-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine at 80℃; for 5h;
  • 7
  • [ 103286-27-7 ]
  • [ 349547-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / CH3ONa / methanol / 0 - 20 °C 2: 72 percent / K2CO3; PPh3 / PdCl2 / dimethylformamide / 5 h / 120 °C
  • 8
  • [ 103286-27-7 ]
  • (R)-5-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 95 percent / CH3ONa / methanol / 0 - 20 °C 2: 72 percent / K2CO3; PPh3 / PdCl2 / dimethylformamide / 5 h / 120 °C 3: 91 percent / BH3*THF / (S)-methyloxazaborolidine / toluene; tetrahydrofuran / 2 h / -20 °C 4: Et3N; DABCO / tetrahydrofuran / 3 h / Heating
Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 130 °C / Inert atmosphere; Glovebox; Schlenk technique 2: water; C28H33N3O2; nickel(II) bromide dimethoxyethane; manganese; lithium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 24 h / 80 °C / Inert atmosphere; Glovebox; Schlenk technique
  • 9
  • [ 103286-27-7 ]
  • (S)-5-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 95 percent / CH3ONa / methanol / 0 - 20 °C 2: 72 percent / K2CO3; PPh3 / PdCl2 / dimethylformamide / 5 h / 120 °C 3: 91 percent / BH3*THF / (S)-methyloxazaborolidine / toluene; tetrahydrofuran / 2 h / -20 °C 4: Et3N; DABCO / tetrahydrofuran / 3 h / Heating
Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 130 °C / Inert atmosphere; Glovebox; Schlenk technique 2: water; C36H49N3O2; nickel(II) bromide dimethoxyethane; manganese; lithium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 24 h / 80 °C / Inert atmosphere; Glovebox; Schlenk technique
  • 10
  • [ 103286-27-7 ]
  • [ 874651-70-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / CH3ONa / methanol / 0 - 20 °C 2: 72 percent / K2CO3; PPh3 / PdCl2 / dimethylformamide / 5 h / 120 °C 3: 91 percent / BH3*THF / (S)-methyloxazaborolidine / toluene; tetrahydrofuran / 2 h / -20 °C
  • 11
  • [ 103286-27-7 ]
  • [ 874651-69-1 ]
YieldReaction ConditionsOperation in experiment
10.1 g (95%) With hydrogenchloride; sodium methylate; benzaldehyde In methanol; sodium hydrogencarbonate 1 1-(2-Bromo-4-methyl-phenyl)-3-phenyl-propenone EXAMPLE 1 1-(2-Bromo-4-methyl-phenyl)-3-phenyl-propenone To a solution of 2-bromo-4-methylacetophenone (7.20 g, 34.0 mmol) and benzaldehyde (3.65 g, 34.0 mmol) in dry methanol (50 ml) was added freshly prepared sodium methoxide (35.7 mmol) in dry methanol (30 ml) at 0° C. The resulting mixture was stirred at 0° C. for 5 h and raised to room temperature over night. 10 ml of HCl (10%) were added slowly and the mixture was evaporated to near dryness under reduced pressure. The residue was suspended in saturated NaHCO3 (50 ml) and extracted with 3*50 ml diethyl ether, washed with brine and dried over MgSO4. Purification by flash chromatography eluding with diethyl ether:pentane 5:95, gave 10.1 g (95%) of the title compound. Rf 0.66 (diethyl ether:pentane 20:80). 1H NMR δ: 2.25 (s, 3H), 6.96 (d, J=10.2 Hz, 1H), 7.15 (d, J=10.2 Hz, 1H), 7.05 (dd, J=7.6 Hz, 2.6 Hz, 1H), 7.24 (m, 3H), 7.34 (m, 2H), 7.40 (m, 3H). 13C NMR δ: 21.4, 112.5, 117.3, 122.5, 122.8, 123.7, 124.9, 128.4, 132.2, 133.6, 133.9, 143.6, 145.3, 186.6.
  • 12
  • [ 103286-27-7 ]
  • [ 40547-58-8 ]
  • [ 174344-19-5 ]
YieldReaction ConditionsOperation in experiment
0.58 g (50%) With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; N-[3-Methyl-2-(4-methyl-benzoyl)-benzofuran-6-yl]acetamide STR73 0.72 g (3.75 mmol) of N-(4-acetyl-3-hydroxy-phenyl)acetamide and 0.81 g (4.1 mmol) of 2-bromo-4-methylacetophenone were dissolved in 5 ml DMF and 1,55 g (11.25 mmol) of potassium carbonate were added. The suspension was heated to 60 C. for 1 h and ethylacetate was added. The organic phase was washed three times with water, one time with a NaCl solution, dried over Na2 SO4 and concentrated in vacuo. The residue was further purified by crystallisation (ethanol). Yield: 0.58 g (50%) Rf =0,12 (III)
0.58 g (50%) With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; EXAMPLE 36 N-[3-Methyl-2-(4-methyl-benzoyl)-benzofuran-6-yl]acetamide STR38 0.72 g (3.75 mmol) of N-(4-acetyl-3-hydroxy-phenyl)acetamide and 0.81 g (4.1 mmol) of 2-bromo-4-methylacetophenone were dissolved in 5 ml DMF and 1,55 g (11.25 mmol) of potassium carbonate were added. The suspension was heated to 60 C. for 1 h and ethylacetate was added. The organic phase was washed three times with water, one time with a NaCl solution, dried over Na2 SO4 and concentrated in vacuo. The residue was further purified by crystallisation (ethanol). Yield: 0.58 g (50%) Rf =0,12 (III)
  • 13
  • [ 103286-27-7 ]
  • [ 42748-90-3 ]
  • 5-chloro-1-(4-methylphenacyl)pyrimidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; triethylamine 5 5-Chloro-1-(4-methylphenacyl)pyrimidin-2-one EXAMPLE 5 5-Chloro-1-(4-methylphenacyl)pyrimidin-2-one A suspension of 5-chloropyrimidin-2-one hydrochloride (501 mg) and 2-bromo-4-methylacetophenone (638 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one and three quarter hours, then cooled and the solid filtered off. The filtrate was evaporated, the residue was diluted with water (100 ml) and the product was extracted with ethyl acetate (3*50 ml). This was combined with the solid and crystallized from acetone: yield 306 mg, m.p. 214°-217° dec: λmaxEtOH 253 nm (ε 19760), 332 nm (ε 2620), λinf 232 nm (ε 11040).
  • 14
  • [ 16982-21-1 ]
  • [ 103286-27-7 ]
  • 4-(4-methylphenyl)-2-thiazolecarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In ethanol; water 5 4-(4-Methylphenyl)-2-thiazolecarboxylic acid (synthesis of starting material) Preparation 5 4-(4-Methylphenyl)-2-thiazolecarboxylic acid (synthesis of starting material) A solution of 2-bromo-4--methylacetophenone (826 mg, 3.76 mmol) and 2-thio-oxamic acid ethyl ester (1 g, 7.51 mmol) in dry ethanol (30 ml) was heated under reflux for 1.5 hours. After distilling off the solvent from the reaction mixture, the residue was treated with water, made weak alkaline (pH 8) with saturated aqueous sodium carbonate and extracted with ethyl acetate. The organic phase was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was dissolved in developing solvent (n-hexane: ethyl acetate 8: 2) and applied on silica gel column. The first fraction (impurities) was discarded and the following fraction (colorless solution) was pooled and concentrated to give viscous product, which was crystallized by adding n-hexane. The crystals were filtered with suction to give 438 mg (yield 47%) of ethyl 4-(4-methylphenyl)-2-thiazolecarboxylate as white solids, m.p. 53-57°C.
  • 15
  • [ 103286-27-7 ]
  • [ 131002-03-4 ]
YieldReaction ConditionsOperation in experiment
20% With tert.-butylhydroperoxide; ammonia; tetra-(n-butyl)ammonium iodide In water at 100℃; for 16h; Green chemistry;
  • 16
  • [ 824-54-4 ]
  • [ 103286-27-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / -78 - 0 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 12 h / Reflux
Multi-step reaction with 2 steps 1: diethyl ether; dibutyl ether / -78 - 0 °C / Inert atmosphere 2: manganese(IV) oxide / chloroform / 18 h / Reflux; Inert atmosphere
Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 3 h / 0 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 °C / Inert atmosphere 2: pyridinium chlorochromate; silica gel / dichloromethane / 20 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C 2: pyridinium chlorochromate / dichloromethane / 0 - 20 °C / Molecular sieve
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 °C / Schlenk technique; Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 20 °C
Multi-step reaction with 2 steps 1: magnesium; iodine / diethyl ether / 3 h / -10 - 0 °C 2: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / -78 - 20 °C / Schlenk technique 2: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Schlenk technique
Multi-step reaction with 2 steps 1.1: magnesium; iodine / diethyl ether 1.2: 3 h / -10 - 0 °C 2.1: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C
Multi-step reaction with 2 steps 1: magnesium; iodine / diethyl ether / 4 h / 0 °C 2: pyridinium chlorochromate / dichloromethane / 20 °C

  • 17
  • 1-(2′-bromo-4′-methylphenyl)ethan-1-ol [ No CAS ]
  • [ 103286-27-7 ]
YieldReaction ConditionsOperation in experiment
85% With silica gel; pyridinium chlorochromate In dichloromethane at 20℃;
79% With manganese(IV) oxide In chloroform for 18h; Reflux; Inert atmosphere;
52% With rhodium(III) chloride hydrate; C13H19N4(1+)*Br(1-) In toluene at 115℃; for 24h; Schlenk technique; Inert atmosphere; 4.3. General procedure for dehydrogenation of alcohol General procedure: RuCl3nH2O (0.5 mol %), HMTA-Bz (1 mol %), alcohol (0.25 ml)and dry toluene (1.0 ml) were placed in a Schlenk tube. The reactionmixture was stirred under open condition to nitrogen andrefluxed for 24 h. After completion of the reaction all toluene wereevaporated under vacuo, the oxidized products were isolated fromcrude mixture with the help of column chromatography using hexane/EtOAc as eluent. The formation of products was confirmed bycomparing the 1H NMR data with literature reports.
With manganese(IV) oxide In dichloromethane for 12h; Reflux; eq. 4 General procedure: Before evacuated and recharged with N2 for 3 times, 2-bromobenzaldehyde derivative (5 mmol) was added to the tube. THF (20 mL) was added to the tube and the mixture was cooled to -78 oC. MeMgCl (1.5-2 eq.) was dropwised to the mixture. The reaction was performed for 1 h at -78 oC, 1 h at 0 oC. 10 mL 2N HCl and 20 mL water were added to the tube and the mixture was extracted with Et2O (10 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 1-(2-bromophenyl)ethanol derivative. 1-(2-bromophenyl)ethanol derivative (3 mmol) and 10 mL CH2Cl2 were added to a 25 mL round-bottom flask. After MnO2 (10 eq., 30 mmol) was added to the mixture slowly, the reaction was heated to reflux for 12 h. After filtration and purification on silica gel, 1-(2-bromophenyl)ethanone derivative was provided, yield 60-84%.
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; Molecular sieve;
With pyridinium chlorochromate In dichloromethane at 20℃;
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 2h;
With pyridinium chlorochromate In dichloromethane at 20℃; for 3h; Schlenk technique;

Reference: [1]Chang, Xin; Chen, Hong-Chao; Li, Chuan-Ying; Ma, Pei-Long; Wang, Peng [Angewandte Chemie - International Edition, 2020, vol. 59, # 23, p. 8937 - 8940][Angew. Chem., 2020, vol. 132, # 23, p. 9022 - 9025,4]
[2]Faggyas, Réka J.; Calder, Ewen D. D.; Wilson, Claire; Sutherland, Andrew [Journal of Organic Chemistry, 2017, vol. 82, # 21, p. 11585 - 11593]
[3]Barteja, Parul; Devi, Preeti; Kannan, Muthukumar; Muthaiah, Senthilkumar [Journal of Catalysis, 2020, vol. 386, p. 1 - 11]
[4]Lou, Zhen-Bang; Pang, Xin-Long; Chen, Chao; Wen, Li-Rong; Li, Ming [Chinese Chemical Letters, 2015, vol. 26, # 10, p. 1231 - 1235]
[5]Ye, Chenghao; Kou, Xuezhen; Xia, Jingzhao; Yang, Guoqiang; Kong, Li; Wei, Quhao; Zhang, Wanbin [Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901]
[6]Acharyya, Ranjan Kumar; Kim, Soyoung; Park, Yeji; Han, Jung Tae; Yun, Jaesook [Organic Letters, 2020, vol. 22, # 20, p. 7897 - 7902]
[7]Wang, Zhixin; Li, Yang; Chen, Fan; Qian, Peng-Cheng; Cheng, Jiang [Chemical Communications, 2021, vol. 57, # 14, p. 1810 - 1813] Shekhar, Chander; Satyanarayana, Gedu [European Journal of Organic Chemistry, 2022, vol. 2022, # 18]
[8]Zhou, Liwei; Qiao, Shujia; Zhou, Fengru; Xuchen, Xinyu; Deng, Guobo; Yang, Yuan; Liang, Yun [Organic Letters, 2021, vol. 23, # 8, p. 2878 - 2883] Zhou, Liwei; Sun, Mingjie; Zhou, Fengru; Deng, Guobo; Yang, Yuan; Liang, Yun [Organic Letters, 2021, vol. 23, # 18, p. 7150 - 7155]
[9]Yoon, Wan Seok; Han, Jung Tae; Yun, Jaesook [Advanced Synthesis and Catalysis, 2021, vol. 363, # 21, p. 4953 - 4959]
  • 18
  • [ 103286-27-7 ]
  • 3-(2-bromo-4-methylphenyl)-6-methylnaphthalen-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With copper(l) iodide; 1,10-Phenanthroline; sodium t-butanolate In toluene at 120℃; for 4h; Inert atmosphere; Sealed tube; General procedure for the preparation of desired compound General procedure: A sealed tube was charged with the mixture of CuI (0.1 mmol, 19.0 mg), 1,10-phenanthroline (0.2 mmol, 36.0 mg), NaOtBu (6 mmol, 0.576 g) and bromine acetophenone derivative 1 (1.0 mmol). The tube was evacuated and recharged with N2 for 3 times. Before toluene (2.0 mL) were added, the tube was sealed and the mixture was allowed to stir at 120 °C for 4 hours. After completion, the mixture was cooled to room temperature, then 2N HCl aq. (1-2 mL) was added and the mixture was extracted with Et2O (5 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel (petroleum ether/diethyl ether: 25/1 to 10/1) provided the corresponding product 3a-l as a solid or yellow oil.
  • 19
  • [ 103286-27-7 ]
  • [ 1779-49-3 ]
  • 2-bromo-4-methyl-1-(prop-1-en-2-yl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-bromo-4-methylacetophenone at 20℃; Inert atmosphere;
86% Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 2-bromo-4-methylacetophenone In tetrahydrofuran Inert atmosphere; 1 Example 1:(1S,3S,3′S)-3,3′,6,6′-tetramethyl-2,2′,3,3′-tetrahydro-1,1′-spirobi[benzo[b] Silole) (Ia)Synthesis In a nitrogen atmosphere, methyltriphenylphosphine bromide (7.1g, 20mmol) and potassium tert-butoxide (2.8g, 25mmol) and 30mL of tetrahydrofuran in a 100mL dry Schlenk tube, after stirring at room temperature for 0.5h, will be dissolved A solution of 1-(2-bromo-4-methylphenyl)ethanone (2.2g, 10.3mmol) in tetrahydrofuran (5mL) was added dropwise to the previous system,The reaction was detected by TLC. The reaction was quenched by adding saturated aqueous ammonium chloride dropwise.Extracted with ethyl acetate three times, the organic phase was washed with saturated brine,Dry over anhydrous sodium sulfate, let stand, remove the desiccant by suction filtration,The filtrate was removed with a rotary evaporator and purified by column chromatography2-bromo-4-methyl-1-(prop-1-en-2-yl)benzene(1.87g, yield: 86%).
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-bromo-4-methylacetophenone In tetrahydrofuran for 2h; Inert atmosphere;
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 2-bromo-4-methylacetophenone In tetrahydrofuran at 20℃; for 36h; Inert atmosphere;
With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 12h;

  • 20
  • [ 75-16-1 ]
  • [ 7697-27-0 ]
  • [ 103286-27-7 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether at 0 - 20℃; Inert atmosphere;
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
  • 21
  • [ 103286-27-7 ]
  • diphenyl(5-methyl-2-(prop-1-en-2-yl)phenyl)silanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 2.3: Cooling
  • 22
  • [ 103286-27-7 ]
  • (S)-3-(bromomethyl)-1,3-dihydro-3,6-dimethyl-1,1-diphenylbenzo[c][1,2]oxasilole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 2.3: Cooling 3.1: (Ra)-4-hydroxy-2,6-bis(2,4,6-triisopropylphenyl)-5,5’,6,6’,7,7’,8,8’-octahydrodinaphtho[1,3,2]dioxaphosphepine 4-oxide; C15H19F4N2(1+)*Cl(1-)*Br2; potassium carbonate / toluene / 4 h / 0 °C / Inert atmosphere
  • 23
  • [ 103286-27-7 ]
  • C22H21BrOSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere 2.3: Cooling 3.1: N-Bromosuccinimide / dichloromethane / 20 °C / Inert atmosphere
  • 24
  • [ 103286-27-7 ]
  • C9H7BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine In dimethyl sulfoxide at 110℃; for 3h;
  • 25
  • [ 103286-27-7 ]
  • [ 544-97-8 ]
  • [ 129167-74-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: dimethyl zinc(II) With titanium tetrachloride In hexane; dichloromethane at -40℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromo-4-methylacetophenone In hexane; dichloromethane at 0℃; Inert atmosphere;
  • 26
  • [ 103286-27-7 ]
  • [ 30086-49-8 ]
  • 3-methyl-5-phenyl-5H-quinazolino[3,2-b]cinnoline-7,13-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 2-bromo-4-methylacetophenone With iodine In dimethyl sulfoxide at 110℃; for 3h; Stage #2: 2-amino-N'-phenylbenzohydrazide With potassium carbonate In dimethyl sulfoxide at 20 - 100℃; for 11h; 16 Example 16 In the reaction flask were successively added 25mL of 2-bromo-5-methyl acetophenone 1b (127mg, 0.6mmol), dimethyl sulfoxide (3mL), and elemental iodine (152mg, 0.6mmol), was heated with stirring at 110 The reaction 3h, cooled to room temperature, 2-aminobenzoic hydrazide 2a (90.8mg, 0.4mmol) and K2CO3 (221mg, 1.6mmol), the reaction was stirred at room temperature for 5h, then stirred and heated at 100 deg.] C 6h. After completion of the reaction, the reaction flask was added saturated ammonium chloride solution to quench the reaction, extracted with dichloromethane, the organic phase was washed with deionized water and saturated sodium chloride solution, dried over anhydrous sodium sulfate. Filtration, rotary evaporation, separating silica gel column (petroleum ether / ethyl acetate = 2/1) to give a yellow solid of 3-methyl-5-phenyl quinazoline -5H- [3,2-b] cinnoline - 7,13-dione 3b (79mg, 56%).
  • 27
  • [ 54655-41-3 ]
  • [ 103286-27-7 ]
  • (1S)-2,3-dihydro-1,5-dimethyl-3-(methylene)indan-1-ol [ No CAS ]
  • C12H14O [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: B-allyl-1,3,2-dioxaborinane With (S)-3,3'-dibromo-1,1'-bi-2-naphthol In toluene at 35℃; for 0.1h; Inert atmosphere; Stage #2: 2-bromo-4-methylacetophenone In toluene at 35℃; for 120h; Inert atmosphere; Stage #3: With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; hydrazine hydrate In toluene at 135℃; for 18h; Inert atmosphere; enantioselective reaction;
  • 28
  • [ 5344-90-1 ]
  • [ 103286-27-7 ]
  • 2-(2-bromo-4-methylphenyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With (6,8,15,17-tetramethyl-7H,16H-5,9,14,18-tetraaza-dibenzo[b,i]-cyclotetradecenato(2-)-k(4)-N,N',N'',N''')nickel(II); potassium <i>tert</i>-butylate In toluene at 90℃; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;
  • 29
  • [ 103286-27-7 ]
  • [ 40545-33-3 ]
  • 2,9-dimethylindolo[2,1-b]quinazoline-6,12-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Following the procedure described in Example 1, 1b (127.8 mg, 0.6 mmol), bisMethylsulfoxide (3 mL) and iodine (152 mg, 0.6 mmol) were added and the mixture was heated and stirred at 110 C. for 3 h, then cooled to room temperature, added2b (60.1 mg, 0.4 mmol), CuBr (11.5 mg, 0.08 mmol) and K2CO3 (221 mg, 1.6 mmol) were added and stirred at room temperatureShould be 5h, then heated to 100 heated reaction 3h. After completion of the reaction, saturated ammonium chloride solution was added to the reaction vessel to quenchThe reaction was extracted with methylene chloride. The combined organic phases were washed with deionized water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. TooThe mixture was filtered, spin-dried and separated on a silica gel column (petroleum ether / ethyl acetate = 2/1, v / v) to obtain 2,9-dimethylindolo [2,1-b]6,12-dione 3 g (75 mg, 68%).
  • 30
  • [ 103286-27-7 ]
  • [ 28144-70-9 ]
  • 9-methylindolo[2,1-b]quinoxazoline-6,12-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: 2-bromo-4-methylacetophenone With iodine In dimethyl sulfoxide at 110℃; for 3h; Stage #2: anthranilic acid amide With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 20 - 100℃; for 8h; 9 Example 9 Following the procedure described in Example 1, 1b (127.8 mg, 0.6 mmol), bisMethylsulfoxide (3 mL) and iodine (152 mg, 0.6 mmol) were added and the mixture was heated and stirred at 110 ° C. for 3 h, then cooled to room temperature, addedAnthranilamide 2a (54.5 mg, 0.4 mmol), CuBr (11.5 mg, 0.08 mmol) and K2CO3 (221 mg,1.6mmol), the reaction was stirred at room temperature for 5h, then heated and stirred at 100 for 3h. After completion of the reaction, add to the reaction vesselThe reaction mixture was quenched with saturated ammonium chloride solution and extracted with methylene chloride. The combined organic phases were washed with deionized water and saturated sodium chloride solutionDistilled, dried over anhydrous sodium sulfate. Filtration, spin-drying, separation of 9-methylindole through a silica gel column (petroleum ether / ethyl acetate = 3/1, v / v)[2,1-b] quinazoline-6,12-dione 3b (61 mg, 58%).
  • 31
  • [ 110-91-8 ]
  • [ 103286-27-7 ]
  • [ 3077-16-5 ]
  • [ 7025-91-4 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In 1,4-dioxane at 140℃; for 16h; Inert atmosphere; Darkness; Overall yield = 72 %; Overall yield = 127.6 mg; 9 4.2. General procedure for the synthesis of aryl amines (3) General procedure: To the mixture of o-bromoacetophenone derivatives 1 (1.0 mmol), t-BuOK (2.0 mmol, 2.0 equiv) and amines 2 (2.0 mmol, 2.0 equiv), dry 1,4-dioxane (5 mL) was added. The mixture was refluxed at 140 °C under N2 without light for 16 h. The reaction was monitored by TLC. Then, the resulting reaction mixture was diluted with water (10 mL), eluting with EtOAc (3 * 15 mL). The organic layer was dried over anhydrous Na2SO4 followed by concentration under reduced pressure and purified by column chromatography using petroleum ether/ethyl acetate to afford the corresponding products.
  • 32
  • [ 103286-27-7 ]
  • [ 536-74-3 ]
  • [ 14635-91-7 ]
  • [ 3287-02-3 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium <i>tert</i>-butylate In 1,4-dioxane at 140℃; for 16h; Inert atmosphere; Darkness; Overall yield = 67 %; Overall yield = 128.8 mg; 5 4.3. General procedure for the synthesis of aryl alkynes (5) General procedure: To the mixture of o-bromoacetophenone derivatives 1 (2.0 mmol, 2.0 equiv), t-BuOK (2.0 mmol, 2.0 equiv) and terminal alkynes 4 (1.0 mmol), dry 1,4-dioxane (5 mL) was added. The mixture was refluxed at 140 °C under N2 without light for 16 h. The reaction was monitored by TLC. Then, the resulting reaction mixture was diluted with water (10 mL), eluting with EtOAc (3 * 15 mL). The organic layer was dried over anhydrous Na2SO4 followed by concentration under reduced pressure and purified by column chromatography using petroleum ether/ethyl acetate to afford the corresponding products.
  • 33
  • [ 103286-27-7 ]
  • (R)-5-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one [ No CAS ]
  • (S)-5-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 130 °C / Inert atmosphere; Glovebox; Schlenk technique 2: N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); benzoic acid; (R)-7,7’-diphenylphosphino-1,1'-spirobiindane / ethylene glycol / 16 h / 100 °C / Inert atmosphere; Glovebox; Schlenk technique
  • 34
  • [ 103286-27-7 ]
  • [ 536-74-3 ]
  • C24H22N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.08 h / Inert atmosphere 1.2: Inert atmosphere; Heating 2.1: methanol / 60 °C / Inert atmosphere
  • 35
  • [ 103286-27-7 ]
  • bis(5-methyl-2-(prop-1-en-2-yl)phenyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C 2.2: -78 - 20 °C 2.3: 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 2.3: -78 °C / Schlenk technique
  • 36
  • [ 103286-27-7 ]
  • (1S,3S,3′S)-3,3′,6,6′-tetramethyl-2,2′,3,3′-tetrahydro-1,1′-spirobi[benzo[b]silole] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C 2.2: -78 - 20 °C 2.3: 0 - 20 °C / Inert atmosphere 3.1: 1,5-hexadienerhodium(I)-chloride dimer; EtDUPHOS / dichloromethane / 12 h / 20 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: Inert atmosphere 2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 2.3: -78 °C / Schlenk technique 3.1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,2-bis((2R,5R)-2,5-diethylphosphoranylidene)benzene / dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 37
  • [ 103286-27-7 ]
  • C10H17BO2 [ No CAS ]
  • C13H14O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; palladium dichloride; XPhos In tetrahydrofuran; water at 70℃;
  • 38
  • [ 103286-27-7 ]
  • C11H19BO2 [ No CAS ]
  • C14H16O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; palladium dichloride; XPhos In tetrahydrofuran; water at 70℃;
  • 39
  • [ 103286-27-7 ]
  • [ 14900-39-1 ]
  • C17H16O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 110℃; for 18h; Schlenk technique; Inert atmosphere;
  • 40
  • [ 947546-75-0 ]
  • [ 103286-27-7 ]
YieldReaction ConditionsOperation in experiment
67% With ethyl 2-hydroxypropionate; water at 110℃; Green chemistry; 3.3. General process for alkyne hydration to form compounds 2 General procedure: Alkynes (2mmol) were added to a stirred 35mL solution of EL:H2O(1:3). The reaction mixture was stirred at 110 °C for a suitable time.After successful conversion, the resultant solution was cooled to roomtemperature and extracted with ethyl acetate (4-6 mL). The combinedorganic phaseswere dehydrated over anhydrous sodium sulfate and filtered.The filtered solution was concentrated under reduced pressureand purified by column chromatography on silica gel (hexane:EtOAcas the eluent) to provide the pure desired product
  • 41
  • [ 103286-27-7 ]
  • C9H7BrO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; selenium(IV) oxide at 90℃; for 5h; Inert atmosphere;
Stage #1: 2-bromo-4-methylacetophenone With pyridine; selenium(IV) oxide at 90℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride; water
With selenium(IV) oxide
  • 42
  • [ 103286-27-7 ]
  • dienyl pinacol boronic ester [ No CAS ]
  • C13H14O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; palladium dichloride; XPhos In tetrahydrofuran; water at 80℃; Schlenk technique;
  • 43
  • [ 103286-27-7 ]
  • [ 552-89-6 ]
  • C16H12BrNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; potassium hydroxide In ethanol at 25℃; for 6h;
  • 44
  • [ 103286-27-7 ]
  • (S)-2,3,5-trimethyl-1'H-spiro[indene-1,2'-quinoline] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide; potassium carbonate / ethanol / 6 h / 25 °C 2: iron; ammonium chloride / ethanol; water / 12 h / 90 °C 3: cobalt(II) iodide; (R,R)-chiraphos; indium; isopropyl alcohol / acetonitrile / 36 h / 60 °C / Inert atmosphere
  • 45
  • [ 103286-27-7 ]
  • 2-(2-bromo-4-methylphenyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; potassium carbonate / ethanol / 6 h / 25 °C 2: iron; ammonium chloride / ethanol; water / 12 h / 90 °C
  • 46
  • [ 103286-27-7 ]
  • [ 74-88-4 ]
  • [ 1437051-59-6 ]
YieldReaction ConditionsOperation in experiment
254.2 mg With iodine; magnesium In diethyl ether at 0℃; for 4h;
  • 47
  • [ 103286-27-7 ]
  • C27H22N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 0 - 80 °C / Inert atmosphere 2: scandium tris(trifluoromethanesulfonate) / dichloromethane / 20 °C / Inert atmosphere 3: (2R)-1-(2,6-diphenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline; bis(η3-allyl-μ-chloropalladium(II)); sodium phosphate / 1,4-dioxane / 17 h / 100 °C / Sealed tube; Inert atmosphere
  • 48
  • [ 103286-27-7 ]
  • C27H23BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 0 - 80 °C / Inert atmosphere 2: scandium tris(trifluoromethanesulfonate) / dichloromethane / 20 °C / Inert atmosphere
  • 49
  • [ 103286-27-7 ]
  • [ 78388-19-9 ]
  • 4-methyl-N-(3-methylbut-2-en-1-yl)-N-(2-oxo-2-(p-tolyl)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With potassium carbonate In acetone Reflux; Inert atmosphere; Sealed tube;
  • 50
  • [ 103286-27-7 ]
  • trifluoro(vinyl)-λ4-borane potassium salt [ No CAS ]
  • 1-(4-methyl-2-vinylphenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; potassium carbonate In 1,4-dioxane; water monomer at 100℃; for 5h; Inert atmosphere; Sealed tube;
Same Skeleton Products
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