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[ CAS No. 1477-19-6 ] {[proInfo.proName]}

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Chemical Structure| 1477-19-6
Chemical Structure| 1477-19-6
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Product Details of [ 1477-19-6 ]

CAS No. :1477-19-6 MDL No. :MFCD00867417
Formula : C17H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RFRXIWQYSOIBDI-UHFFFAOYSA-N
M.W : 266.29 Pubchem ID :255968
Synonyms :
Fragivix;L 2197;Venagil;Vasoc;Benzarona;Benzaronum;NSC 82134
Chemical Name :(2-Ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone

Calculated chemistry of [ 1477-19-6 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 77.88
TPSA : 50.44 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.61
Log Po/w (XLOGP3) : 4.27
Log Po/w (WLOGP) : 3.93
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 4.21
Consensus Log Po/w : 3.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.54
Solubility : 0.00771 mg/ml ; 0.000029 mol/l
Class : Moderately soluble
Log S (Ali) : -5.04
Solubility : 0.00242 mg/ml ; 0.00000909 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.97
Solubility : 0.000285 mg/ml ; 0.00000107 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.04

Safety of [ 1477-19-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P273-P301+P312-P330 UN#:N/A
Hazard Statements:H302-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1477-19-6 ]

* 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.

  • Upstream synthesis route of [ 1477-19-6 ]
  • Downstream synthetic route of [ 1477-19-6 ]

[ 1477-19-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 3343-80-4 ]
  • [ 1477-19-6 ]
YieldReaction ConditionsOperation in experiment
90% With sodium thioethylate In N,N-dimethyl-formamide at 125 - 130℃; for 1 h; In a RBF/SB (50 mL), benzofuran (12; 1.00 g; 3.57 mmol) was diluted with DMF (18 mL) and NaSEt (455 mg) was added. The mixture was heated (125-130 °C; 1.0 h). Next, the mixture was quenched (2 vol NH4CI aq) and extracted with EtOAc (4 x 75 mL). The organic phase was washed with H20, followed by NaCl aq. The organic phase was then dried (MgS04), filtered, concentrated under reduced pressure and purified via Si02 chromatography (4:1 ; Hex:EtOAc) to give 13 as a white solid (857 mg; 3.22 mmol; 90percent yield). 1H-NMR (400 MHz) CDC13: 10.4 (bs, 1H; exchangeable in D20), 7.80-7.78 (d, 2H), 7.49-7.47 (d, 1H), 7.43-7.41 (d, 1H), 7.30-7.26 (t, 1H), 7.22-7.18 (t, 1H), 6.98-6.94 (d, 2H), 2.95-2.89 (q, 2H), 1.36-1.32 (t, 3H); 13C-NMR (100 MHz) CDC13: 192.1, 165.9, 161.5, 153.6, 132.2, 130.9, 129.0, 124.4, 123.5, 121.1, 1 16.1, 115.6, 1 1 1.0, 21.8, 12.2. LC MS-MS: 267.0 -> 121.2 m/z; GS1 and GS2 at 20, DP = 46, CE = 29, CXP = 6, tR = 4.31 min.
77.2% With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 110℃; for 3 h; Ethanethiol (8 mL) was added dropwise to a suspension of sodium hydride (640 mg, 16.0 mmol) in dry THF (15 mL) under ice-water bath. Stir for 5 minutes. A large number of solid precipitation. The solvent was distilled off under reduced pressure. DMF (20 mL) was then added to the residue. The reaction solution A was obtained. A solution of compound 2 (3.0 g, 10.7 mmol) in DMF (20 mL) was added dropwise to reaction solution A. Followed by stirring at 110°C for 3 hours. Cooled to room temperature. Water (120 mL) was added. Extraction with ethyl acetate (60 mL x 3). The combined organic phases were washed with saturated brine (30 mL x 2). Dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The product was purified by column chromatography (200-300 mesh silica gel, ethyl acetate: petroleum ether = 1:50 to 1: 6) to obtain (2-ethylbenzofuran-3-yl)(4-hydroxyphenyl)methanone (3) (2.2 g). The yield was 77.2percent.
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2701 - 2713
[2] Patent: WO2012/48058, 2012, A2, . Location in patent: Page/Page column 14-15
[3] Patent: CN106065010, 2016, A, . Location in patent: Paragraph 0061; 0064
[4] Journal of the Chemical Society, 1957, p. 625,627
  • 2
  • [ 3131-63-3 ]
  • [ 100-07-2 ]
  • [ 1477-19-6 ]
YieldReaction ConditionsOperation in experiment
68.2% With lewis acid In chloroform at 10 - 30℃; for 4 h; (1) To a 500 mL reaction vessel, 112 g of chloroform, 36 g of 2-ethylbenzofuran, and 72 g of p-methoxybenzoyl chloride were added, and then a feed tube was washed by further adding 50 g of chloroform. When cooling to 10-30 ° C, then the first addition of Lewis acid 17g; cooling to the last temperature range for the second time plus Lewis acid 17g; cooling to the last temperature range for the third time to add Lewis acid 17g,a total of 51g of Lewis acid was added, and the temperature was kept constant at 15-30 ° C for 4 h;(2) After the completion of the heat preservation reaction, tap water is quenched; acidified with 110 g of dilute hydrochloric acid (10percent).Then, the heating is started to 65-70 ° C, and the stirring is kept for 0.5 hour; the stirring is stopped for 0.5 hours, and then the liquid is separated, and the material in the reactor is washed twice with hot water of about 70 ° C.The washed material is sucked into the reactor for distillation under reduced pressure; after the distillation is completed, it is slightly lowered.The temperature was about 65 ° C, and 35 g of methanol was further added thereto, and the mixture was cooled, cooled, and crystallized by freezing, filtered, and dried to obtain 60 g of a benzalkonone intermediate (white solid).(3) Add 140g of chloroform, benzalkonone intermediate dry product 60g, add 30g of chloroform rinse feed pipe to the clean 500ml reactor; pass the cooling water to reduce the temperature inside the reactor, when the temperature is stable at 15-30 At a temperature of °C, 43g of Lewis acid was added at a time, and stirred under the action of cooling water for 0.5 hours; after the completion of the stirring, the temperature was raised to 90-95 ° C, and the heat preservation was started.Should be 2-3h; after the reaction is completed, pass the cooling water and start to cool down to 20-30 °C;(4) After cooling for 3 hours, add water to quench; add 130 g of dilute hydrochloric acid (10percent) to acidify, stir for half an hour, then warm to 90-95 ° C, stir for half an hour to separate the liquid; after the liquid separation, use 70 ° C or so Washed twice, will wash the finished materialDistillation was carried out, acetonitrile and petroleum ether were added to cool and crystallize, and after filtration, it was rinsed with an appropriate amount of solvent to obtain a crude benzalkonium. Then, 40 g of the obtained benzalkonone crude product and 70 g of acetonitrile and petroleum ether were charged into the reactor, activated carbon was added, and the temperature was immediately maintained by heating and refluxing for 0.5 hour.It was filtered with a precision filter under air pressure, cooled, crystallized, filtered, and dried to obtain 35 g of benzalkonone, and the yield of the final product was 68.2percent.
Reference: [1] Patent: CN108440469, 2018, A, . Location in patent: Paragraph 0016-0030
  • 3
  • [ 3562-84-3 ]
  • [ 1477-19-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 5, p. 1122 - 1125
  • 4
  • [ 3131-63-3 ]
  • [ 1477-19-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 1682,1685
[2] Journal of the Chemical Society, 1957, p. 625,627
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2701 - 2713
[4] Patent: WO2012/48058, 2012, A2,
[5] Patent: CN106065010, 2016, A,
  • 5
  • [ 100-07-2 ]
  • [ 1477-19-6 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 625,627
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2701 - 2713
  • 6
  • [ 1646-26-0 ]
  • [ 1477-19-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2701 - 2713
[2] Patent: WO2012/48058, 2012, A2,
  • 7
  • [ 90-02-8 ]
  • [ 1477-19-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2701 - 2713
[2] Patent: CN106065010, 2016, A,
  • 8
  • [ 100-52-7 ]
  • [ 1477-19-6 ]
Reference: [1] Patent: WO2012/48058, 2012, A2,
  • 9
  • [ 90908-77-3 ]
  • [ 1477-19-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 1682,1685
  • 10
  • [ 27914-73-4 ]
  • [ 1477-19-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 1682,1685
  • 11
  • [ 3131-63-3 ]
  • [ 1486-50-6 ]
  • [ 101596-43-4 ]
  • [ 1477-19-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 1682,1685
  • 12
  • [ 1477-19-6 ]
  • [ 3562-84-3 ]
YieldReaction ConditionsOperation in experiment
35% for 0.25 h; In a RBF/SB (50 mL), hydroxy-benzofuran (13; 318 mg; 1.19 mmol) was diluted with AA (20 mL) and then Br2 (138 μ) was added. After 15 min, the mixture was quenched with H20 (35 mL) and extracted with EtOAc (3 x 70 mL). The organic phase was washed NaCl aq (2 x 50 mL) and dried (MgS04), filtered, concentrated under reduced pressure, and purified via Si02 chromatography (3:1 ; Hex:EtOAc) to give 7 as a light red solid (176 mg; 0.469 mmol; 35percent yield). 1H-NMR (400 MHz) DMSO-d6: 10.2 (bs, 1H; exchangeable in D20), 7.91 (s, 2H), 7.66-7.64 (d, 1H), 7.43-7.41 (d, 1H), 7.36-7.33 (t, 1H), 7.29-7.27 (d, 1H), 2.83-2.77 (q, 2H), 1.28-1.24 (t, 3H); 13C-NMR (100 MHz) DMSO-d6: 187.5, 165.8, 156.1, 153.5, 133.7,132.3, 126.9, 125.2, 124.3, 121.2, 1 15.6, 1 12.2, 1 11.7, 21.84, 12.4. LC/MS-MS: 424.9 -> 278.8 m/z; GS1 and GS2 at 20, DP = 96, CE = 37, CXP = 16, tR = 4.65 min.
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2701 - 2713
[2] Patent: WO2012/48058, 2012, A2, . Location in patent: Page/Page column 15
[3] Journal of the Chemical Society, 1957, p. 625,627
[4] Patent: US5266711, 1993, A,
  • 13
  • [ 1477-19-6 ]
  • [ 68-90-6 ]
  • [ 3562-84-3 ]
Reference: [1] Patent: US4766223, 1988, A,
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