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[ CAS No. 56317-21-6 ]

{[proInfo.proName]} (Synonyms:Moracin-M) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 56317-21-6
Chemical Structure| 56317-21-6
Structure of 56317-21-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 56317-21-6 ]

CAS No. :56317-21-6 MDL No. :MFCD17166969
Formula : C14H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :LHPRYOJTASOZGJ-UHFFFAOYSA-N
M.W :242.23 g/mol Pubchem ID :185848
Synonyms :

1. Moracin M

Calculated chemistry of [ 56317-21-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 67.72
TPSA : 73.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 3.22
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.73
Solubility : 0.0449 mg/ml ; 0.000185 mol/l
Class : Soluble
Log S (Ali) : -4.13
Solubility : 0.0179 mg/ml ; 0.0000738 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0199 mg/ml ; 0.0000822 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.81

Safety of [ 56317-21-6 ]

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

Application In Synthesis of [ 56317-21-6 ]

* 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 [ 56317-21-6 ]

[ 56317-21-6 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 112768-54-4 ]
  • [ 112768-53-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Yield given. Multistep reaction;
  • 2
  • [ 112768-55-5 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
86% With tetrabutyl ammonium fluoride In tetrahydrofuran for 48h; Ambient temperature;
86% With tetrabutyl ammonium fluoride In tetrahydrofuran for 16h; Ambient temperature;
  • 3
  • [ 134937-20-5 ]
  • [ 56317-21-6 ]
  • [ 134979-08-1 ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 18% With boron tribromide In dichloromethane for 480h; Ambient temperature;
  • 4
  • [ 134937-19-2 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
12.3% With formic acid for 1h; Heating;
  • 5
  • [ 56317-21-6 ]
  • [ 74-88-4 ]
  • [ 73343-39-2 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetone Heating;
YieldReaction ConditionsOperation in experiment
Oxyresveratrol-tetraacetat, 1) Br2, 2) KOH in CH3OH, 3) HOAc;
  • 7
  • [ 863310-53-6 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In ethanol
  • 8
  • 3-(3,5-bis-benzyloxy-phenyl)-7-hydroxy-chromen-2-one [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: K2CO3 / acetone 2: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 3: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 4: hydrogen / Pd-C / ethanol
  • 9
  • [ 863310-42-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 2: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 3: hydrogen / Pd-C / ethanol
  • 10
  • [ 863310-61-6 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 2: hydrogen / Pd-C / ethanol
  • 11
  • [ 2732-96-9 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: KOAc / acetic anhydride / 10 h / 150 °C 2: K2CO3 / acetone 3: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 4: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 5: hydrogen / Pd-C / ethanol
  • 12
  • [ 95-01-2 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: KOAc / acetic anhydride / 10 h / 150 °C 2: K2CO3 / acetone 3: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 4: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 5: hydrogen / Pd-C / ethanol
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 2.2: 0.08 h / 0 °C 2.3: 14.5 h / 0 - 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4.1: boron tribromide / dichloromethane
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane 2: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4: boron tribromide / dichloromethane
Multi-step reaction with 5 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 2.2: 0.08 h / 0 °C 2.3: 14.5 h / 0 - 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane 2: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 5: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
Multi-step reaction with 3 steps 1.1: triphenylphosphine; zinc / acetonitrile / 1 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: caesium carbonate; copper(l) iodide / acetonitrile / 3 h / 80 °C / Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating

  • 14
  • [ 50551-63-8 ]
  • [ 56317-21-6 ]
  • 15
  • [ 112768-54-4 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) BuLi, Me3SnCl, 2) Pd(PPh3)4 / 1) THF, rt, 1 h, 2) THF, reflux 2: 86 percent / Bu4NF / tetrahydrofuran / 16 h / Ambient temperature
  • 16
  • [ 108-46-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: trichlorophosphate / acetonitrile 2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 3.2: 0.08 h / 0 °C 3.3: 14.5 h / 0 - 20 °C 4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5.1: boron tribromide / dichloromethane
Multi-step reaction with 5 steps 1: trichlorophosphate / acetonitrile 2: dmap; triethylamine / dichloromethane 3: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 4: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5: boron tribromide / dichloromethane
Multi-step reaction with 6 steps 1.1: trichlorophosphate / acetonitrile 2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 3.2: 0.08 h / 0 °C 3.3: 14.5 h / 0 - 20 °C 4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
Multi-step reaction with 6 steps 1: trichlorophosphate / acetonitrile 2: dmap; triethylamine / dichloromethane 3: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 4: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

  • 17
  • [ 2150-44-9 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 3: 12.3 percent / 90percent HCO2H / 1 h / Heating
  • 18
  • [ 2150-37-0 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 52 percent / 90percent HCO2H / 1 h / Heating 3: 18 percent / BBr3 / CH2Cl2 / 480 h / Ambient temperature
  • 19
  • [ 132552-87-5 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 52 percent / 90percent HCO2H / 1 h / Heating 3: 18 percent / BBr3 / CH2Cl2 / 480 h / Ambient temperature
Multi-step reaction with 2 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO2H / 1 h / Heating
  • 20
  • [ 103929-83-5 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO2H / 1 h / Heating
  • 21
  • [ 134937-22-7 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 52 percent / 90percent HCO2H / 1 h / Heating 2: 18 percent / BBr3 / CH2Cl2 / 480 h / Ambient temperature
  • 22
  • [ 112768-53-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: 86 percent / TBAF / tetrahydrofuran / 48 h / Ambient temperature
  • 23
  • [ 1332302-64-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
2.1 mg In [D3]acetonitrile at 80℃; for 8h;
  • 24
  • [ 50841-50-4 ]
  • [ 108-46-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminum oxide / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Reflux 2: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere
  • 25
  • [ 73343-39-2 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran With boron tribromide In dichloromethane at -78 - 25℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In dichloromethane Schlenk technique; Inert atmosphere; Cooling with ice;
70% With boron tribromide In dichloromethane at -78 - 20℃; for 3h; Inert atmosphere; 7-(6-Hydroxybenzofuran-2-yl)-2,2-dimethylchroman-5-ol,Wittifuran D (11): General procedure: To a stirred solutionof 8 (100 mg, 0.28 mmol) in dry DCM (4 mL) at 78 C under nitrogen conditions wasadded dropwise 1-M BBr3 solution in CH2Cl2 (1.4 mL, 1.42 mmol) and stirred at the sametemperature for 2 h, then room temperature for 1 h. After completion of the reaction, theexcess BBr3 was quenched by adding ice water at 0 C. The reaction mixture was warmedto room temperature and extracted with ethyl acetate 2 times. The combined organic layerwas dried over MgSO4, filtered, and evaporated. The residue was purified by silica gelcolumn chromatography (Hex:EtOAc = 7:3, v/v) to afford compound 11 (50 mg, 60% yield)as a white solid:
Stage #1: 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran With boron tribromide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Stage #2: With methanol In dichloromethane at 0℃; 13 Example 13: Preparation of 5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol, with the following structural formula: [Show Image]; This compound was prepared using Method A from resorcinol and 2-bromo-1-(3,5-dimethoxyphenyl)ethanone: Yield 25% following procedures A.2 and A.5; m.p. 168°C (dec.); IR 3355, 2931, 1613, 1432, 1293, 1145 cm-1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.52 (s, 1H), 9.37 (s, 2H), 7.38 (d, J = 8.4 Hz, 1H), 7.06 (s, 1H), 6.92 (s, 1H), 6.74 (d, J = 8.3 Hz, 1H), 6.68 (s, 2H), 6.21 (s, 1H); 13C-NMR (126 MHz, δ ppm, CD3O) 160.1, 157.4, 156.9, 156.3, 133.9, 123.2, 122.1, 113.4, 104.1, 103.7, 102.3, 98.6.
  • 26
  • [ 134937-20-5 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
92% With aluminum (III) chloride In chloroform at 65℃; for 9h; 1.4 Example 1 2- (3,5-Dimethoxyphenyl) -6-hydroxybenzofuran (10 mmol, 2.70 g), aluminum trichloride(40 mmol, 5.33 g) was added to 50 ml of chloroform, stirred, heated to 65 ° C, 9 h reaction;After completion, the solution was cooled to room temperature, filtered, washed with water (10 ml x 3), dried over anhydrous magnesium sulfate and concentrated.The alcohol was recrystallized to give 2.23 g of white Moracin M as a solid in 92% yield.
88% With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere; Schlenk technique;
88% With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere; 27.2 (2) Take 2- (3,5-dimethoxyphenyl) benzofuran-6-phenol (M18, 40.5mg, 0.15mmol, 1.0eq.)5 ml of dry methylene chloride was added, and boron tribromide (3.0 eq., 1 mmol / mL methylene chloride solution) was added dropwise under a nitrogen atmosphere at -78 ° C, and the reaction was raised to room temperature and stirred for 8 hours. Slowly add 2 mL of water to quench the reaction. Extracted with ethyl acetate (10mL x 3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (eluent PE / EA = 10/1) to obtain the product Moracin M (P4-3) (32mg, 88%). Characteristic data is consistent with literature data.
86% With aluminum (III) chloride In 1,2-dichloro-ethane at 80℃;
26% With aluminum oxide In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux;
25% With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere;
25% With boron tribromide In dichloromethane at 0℃;
25% With boron tribromide In dichloromethane
Multi-step reaction with 2 steps 1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 2: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference: [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104447646, 2016, B Location in patent: Paragraph 0034
[2]Cao, Tongxiang; Jiang, Huanfeng; Zhang, Ling; Zhu, Shifa [Angewandte Chemie - International Edition, 2020, vol. 59, # 12, p. 4670 - 4677][Angew. Chem., 2020, vol. 132, p. 4700 - 4707,8]
[3]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY; GENIFARM GUANGZHOU TECH; XINYUAN GUANGZHOU PHARMACEUTICAL RES - CN110894192, 2020, A Location in patent: Paragraph 0164-0166; 0168
[4]Xu, Tianlong; Zhang, Ensheng; Wang, Dejian; Wang, Yan; Zou, Yong [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4313 - 4324]
[5]Lee, Ju Hee; Ko, Hae Ju; Woo, Eun-Rhan; Lee, Sang Kook; Moon, Bong Soo; Lee, Chan Woo; Mandava, Suresh; Samala, Mallesham; Lee, Jongkook; Kim, Hyun Pyo [European Journal of Pharmacology, 2016, vol. 783, p. 64 - 72]
[6]Location in patent: experimental part Arias, Leire; Vara, Yosu; Cossio, Fernando P. [Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 266 - 275]
[7]Lee, Jae Jun; Yun, So-Ra; Jun, Jong-Gab [Bulletin of the Korean Chemical Society, 2014, vol. 35, # 12, p. 3453 - 3458]
[8]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[9]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]
[10]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
  • 27
  • [ 6626-15-9 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium diacetate; copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate / 72 h / 40 °C / Inert atmosphere 3.1: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 4.1: boron tribromide / dichloromethane / 0 °C
  • 28
  • [ 66417-41-2 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate / 72 h / 40 °C / Inert atmosphere 2: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 3: boron tribromide / dichloromethane / 0 °C
  • 29
  • 1-(2,4-diacetoxyphenyl)-2-(3,5-dimethoxyphenyl)acetylene [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 2: boron tribromide / dichloromethane / 0 °C
  • 30
  • (E)-2-(2-bromo-4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 2: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 3: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C
  • 31
  • 2-(3,5-dimethoxyphenyl)-6-hydroxybenzofuran-3-carboxylic acid [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 2: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C
  • 32
  • [ 88491-44-5 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C 2: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 3: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 4: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C
Multi-step reaction with 4 steps 1: acetic anhydride; triethylamine / 7 h / 110 °C 2: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 3: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 4: aluminum (III) chloride / chloroform / 9 h / 65 °C
  • 33
  • [ 7311-34-4 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C 2: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 3: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 4: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C
Multi-step reaction with 4 steps 1: acetic anhydride; triethylamine / 7 h / 110 °C 2: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 3: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 4: aluminum (III) chloride / chloroform / 9 h / 65 °C
  • 34
  • [ 299912-77-9 ]
  • [ 56317-21-6 ]
  • 35
  • (1-benzofuran-6-yloxy)(tert-butyl)dimethylsilane [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: -78 - 20 °C 1.3: 20 °C / pH 5 2.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 3.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 4.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux
  • 36
  • (6-[tert-butyl(dimethyl)silyl]oxy}-1-benzofuran-2-yl)boronic acid [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 2: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 3: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux
  • 37
  • [ 218444-38-3 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
75% With n-butyllithium; diphenylphosphane In tetrahydrofuran; hexane for 36h; Inert atmosphere; Reflux; 5-(6-Hydroxybenzofuran-2-yl)-2-(3-methyl-2-butenyl)-1,3-benzenediol (1) General procedure: ). n-Butyllithium (2.4 M inhexane, 2.25 mL, 5.4 mmol) was added over 1 h to a stirred solution ofdiphenylphosphine (940 μL, 5.4 mmol) in dry THF (8 mL) at 0°C under nitrogen. 34 (404 mg, 0.9 mmol) in dry THF (4 mL) wasadded and the solution was allowed to warm to room temperature. The mixture washeated under reflux for 36 h and was then poured into 4 M aqueous sodiumhydroxide (8 mL), acidified with 4 M aqueous HCl and extracted into ethylacetate. The organic extract was dried with anhydrous sodium sulfate and thesolvent removed in vacuo.
  • 38
  • [ 6272-26-0 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol / 4 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: -78 - 20 °C 3.3: 20 °C / pH 5 4.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 5.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 6.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux
  • 39
  • 2-(2-bromo-4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 2: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 3: aluminum (III) chloride / chloroform / 9 h / 65 °C
  • 40
  • tris(3,5-dimethoxyphenyl)bismuthine [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

  • 41
  • [ 52924-53-5 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 1.2: 0.08 h / 0 °C 1.3: 14.5 h / 0 - 20 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3.1: boron tribromide / dichloromethane
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 1.2: 0.08 h / 0 °C 1.3: 14.5 h / 0 - 20 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 4.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
  • 42
  • [ 41777-08-6 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3: boron tribromide / dichloromethane
Multi-step reaction with 4 steps 1: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 4: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
  • 43
  • [ 218444-37-2 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
81% With boron tribromide In dichloromethane at -78 - 20℃; for 24h;
  • 44
  • C12H10Br2O4 [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
  • 45
  • C10H8Br2O3 [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
  • 46
  • 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diol [ No CAS ]
  • 2-bromobenzofuran-6-ol [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
83% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide for 1h; Inert atmosphere; Heating;
  • 47
  • [ 106120-04-1 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating
  • 48
  • 4-(2,2-dibromovinyl) benzene-1,3-diol [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; copper(l) iodide / acetonitrile / 3 h / 80 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating
  • 49
  • 5-((3,5-dimethoxyphenyl)ethynyl)-2-methyl-4H-pyran-4-one [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: indium(III) triflate / tetrahydrofuran / 12 h / 100 °C / Inert atmosphere; Schlenk technique 2: boron tribromide / dichloromethane / 8 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
  • 50
  • [ 397333-51-6 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 2.2: Schlenk technique; Inert atmosphere; Cooling with ice
  • 51
  • 6-diazo-3-methoxycyclohexa-2,4-dien-1-one [ No CAS ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone; dichloromethane / 7 h / 55 °C / Schlenk technique; Inert atmosphere; Sealed tube 2.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 3.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 3.2: Schlenk technique; Inert atmosphere; Cooling with ice
  • 52
  • [ 40925-70-0 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium nitrite; hydrogenchloride / ethanol; water / 2.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.1: potassium carbonate / acetone; dichloromethane / 7 h / 55 °C / Schlenk technique; Inert atmosphere; Sealed tube 3.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 4.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 4.2: Schlenk technique; Inert atmosphere; Cooling with ice
  • 53
  • [ 41046-70-2 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 1.2: 15 h / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
  • 54
  • [ 171290-52-1 ]
  • [ 56317-21-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 1.2: 15 h / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
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