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[ CAS No. 579-74-8 ] {[proInfo.proName]}

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Chemical Structure| 579-74-8
Chemical Structure| 579-74-8
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Product Details of [ 579-74-8 ]

CAS No. :579-74-8 MDL No. :MFCD00008725
Formula : C9H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DWPLEOPKBWNPQV-UHFFFAOYSA-N
M.W : 150.17 Pubchem ID :68481
Synonyms :

Calculated chemistry of [ 579-74-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.13
TPSA : 26.3 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) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 2.16
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.19
Solubility : 0.971 mg/ml ; 0.00647 mol/l
Class : Soluble
Log S (Ali) : -1.99
Solubility : 1.53 mg/ml ; 0.0102 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.216 mg/ml ; 0.00144 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 579-74-8 ]

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

Application In Synthesis of [ 579-74-8 ]

* 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 [ 579-74-8 ]
  • Downstream synthetic route of [ 579-74-8 ]

[ 579-74-8 ] Synthesis Path-Upstream   1~9

  • 1
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  • [ 31949-21-0 ]
YieldReaction ConditionsOperation in experiment
96% With copper(ll) bromide In chloroform; ethyl acetate at 70℃; for 8 h; Inert atmosphere; Reflux Copper (II) bromide (2.97 g, 6.66 mmol) was placed in a twonecked round-bottomed flask fitted with a reflux condenser. EtOAc (10.0 mL) was added to it and the mixture was stirred at 70C for 5 min under nitrogen atmosphere. 1-(2-Methoxyphenyl)ethanone (6) (0.50 g, 3.33 mmol) in CHCl3 (10.0 mL) was slowly added to it and then the mixture was refluxed for 8 h. After completion of the reaction, it was cooled to room temperature, filtered through Celite® pad, and washed with EtOAc (20 mL). The filtrate was concentrated under reduced pressure. The crude was puri- fied by column chromatography (EtOAc:hexane = 1:4) to afford the pure product 7a (0.73 g, 96percent) as brown liquid. Rf = 0.43 (EtOAc/hexane = 1/4); 1 H NMR (300 MHz, CDCl3): δ 7.81 (1H, dd, J = 7.8, 1.8 Hz), 7.52 (1H, td, J = 7.8, 1.8 Hz), 7.05–6.96 (2H, m), 4.61 (2H, s), 3.94 (3H, s); 13C NMR (75 MHz, CDCl3): δ 192.3, 158.8, 134.9, 131.6, 124.9, 121.2, 111.7, 56.0, 38.0.
83%
Stage #1: at 60℃;
Stage #2: at 60℃; for 0.25 h;
General procedure: The round-bottom flask containing acetophenone derivative 1, 10 (4 mmol) and PTSA (0.076 g,0.4 mmol) was heated to 60 °C to turn the reaction mixture into a paste and NBS (0.854 g, 4.8 mmol) thenadded slowly. After 15 min, the reaction mixture was cooled to room temperature and water (20 mL)added. The crude product was extracted with dichloromethane (2 x 20 mL), dried over anhydrousNa2SO4 and purified by crystallization from n-hexane–dichloromethane to give pure product. 2-Methoxyphenacyl bromide (2): Yellow solid, soluble in acetone, dichloromethane, chloroform, insolublein water; yield 83percent; m.p.: 43–45 °C; 1H-NMR (500 MHz, CDCl3) (δ, ppm): 7.78 (dd, 1H, J = 1.5,7.5 Hz, Ar–H), 7.51–7.47 (m, 1H, Ar–H), 7.02–6.96 (m, 2H, Ar–H), 4.57 (s, 2H, CH2), 3.93 (s, 3H, OCH3).This result showed consistency with the data in literature [26].
330 g With bromine In acetonitrile at 20 - 25℃; for 4 h; 1 -(2-methoxyphenyl)ethan-1 -one 2-bromo-1 - MW: 150.17 (2-methoxyphenyl)ethan-1-one MW: 229.07 [00242] l-(2-methoxyphenyl)ethanone, 1.1, (300 g, 1.0 eq) was added to a reactor containing acetonitrile (1.2 L, 4.0 V). Br2 (319.62 g, 1.0 eq) was added by cooling the reaction to below 25°C. The reaction mixture was stirred for 4 h at 20-25 °C and sampled for IPC until the content of l-(2-methoxyphenyl)ethanone was 6.5percent. NaHSCb (600 ml, 2V) was added to quench the reaction and then stirred for an additional 0.5h at 20-25°C. Product was extracted with methyl tert-butyl ether (600 ml, 2V), three times, to yield a black oil (418 g, crude), which was purified using a column to yield 330 g of 2-bromo-l-(2-methoxyphenyl)ethan-l-one, 1.2, as an off-white solid (98percent purity).
Reference: [1] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 12, p. 1481 - 1485
[2] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4707 - 4710
[3] Tetrahedron Letters, 2009, vol. 50, # 6, p. 700 - 703
[4] Chemistry - A European Journal, 2011, vol. 17, # 28, p. 7953 - 7959
[5] Molecules, 2017, vol. 22, # 5,
[6] Dalton Transactions, 2008, # 6, p. 822 - 831
[7] Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1497 - 1502
[8] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1170 - 1176
[9] Australian Journal of Chemistry, 1994, vol. 47, # 11, p. 2001 - 2012
[10] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 4, p. 719 - 722
[11] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1291 - 1295
[12] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1297 - 1303
[13] Tetrahedron, 2008, vol. 64, # 22, p. 5191 - 5199
[14] Chemistry - An Asian Journal, 2010, vol. 5, # 10, p. 2258 - 2265
[15] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 403 - 412
[16] Angewandte Chemie - International Edition, 2013, vol. 52, # 44, p. 11632 - 11636[17] Angew. Chem., 2013, vol. 125, # 44, p. 11846 - 11850,5
[18] Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3570 - 3574
[19] Chemical Communications, 2014, vol. 50, # 51, p. 6726 - 6728
[20] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582
[21] Journal of Materials Chemistry A, 2015, vol. 3, # 12, p. 6258 - 6264
[22] MedChemComm, 2015, vol. 6, # 6, p. 1036 - 1042
[23] European Journal of Medicinal Chemistry, 2015, vol. 104, p. 1 - 10
[24] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 8, p. 1166 - 1173
[25] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674
[26] Angewandte Chemie - International Edition, 2016, vol. 55, # 29, p. 8444 - 8447[27] Angew. Chem., 2016, vol. 128, # 29, p. 8584 - 8587,4
[28] Patent: KR101642378, 2016, B1, . Location in patent: Paragraph 0062-0066
[29] ChemMedChem, 2018, vol. 13, # 1, p. 37 - 47
[30] Patent: US2018/44459, 2018, A1, . Location in patent: Paragraph 0367
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[32] Patent: US2018/44284, 2018, A1, . Location in patent: Paragraph 0175; 0176
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[34] Patent: WO2018/161008, 2018, A1, . Location in patent: Paragraph 00241-00242
[35] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
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  • [ 31949-21-0 ]
  • [ 1121543-12-1 ]
Reference: [1] Biochemistry, 2010, vol. 49, # 36, p. 7913 - 7919
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  • [ 445-82-9 ]
Reference: [1] Chemical Communications, 2000, # 14, p. 1323 - 1324
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  • [ 16740-73-1 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; iodine In acetonitrile for 12 h; Darkness General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)
95% With hydrogenchloride; N-Bromosuccinimide In water; acetone at 20℃; for 3 h; Compound 41-2 (0492) To a solution of 41-1 (2.0 g, 13.32 mmol) in acetone (25 mL) was added NBS (2.37 g, 13.32 mmol) and 1M HCl aq. (0.13 mL, 0.13 mmol). The reaction mixture was stirred at room temperature for 3 h, and then concentrated to dryness under reduced pressure. The residue was dissolved with PE (40 mL) the resultant precipitate was filtered and dried in vacuum to afford 41-2 as a white solid (2.90 g, yield: 95percent).
Reference: [1] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
[2] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4707 - 4710
[3] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 312-313
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1423 - 1428
[5] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504
  • 5
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  • [ 40023-74-3 ]
YieldReaction ConditionsOperation in experiment
72% With ammonium hydroxide; ammonium acetate; sodium cyanoborohydride; zinc In ethanol; water at 80℃; for 36 h; General procedure: To a saturated solution of NH4OAc in EtOH (40 mL) were added activated Zn (5 equiv), acetophenone (1 equiv), NaBCNH3(3 equiv) and 30percent aq NH3 (10 mL) respectively. The mixture wasstirred at 80 C for 36 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and made basic using 1 M NaOH (50 mL). Theorganic phase was separated and aqua phase was extracted with (2x25 mL) CH2Cl2. The organic phases were combined and acidified with HCl (pH: 2.0). The organic layer was separated andH2O layer was extracted with CH2Cl2 (2 25 mL). The H2O layer was made basic with NaOH (pH: 10.0), The organic layer was extracted with CH2Cl2 (3 25 mL). Combined organic layers weredried over Na2SO4 and evaporation of the solvent afforded thedesired amines.
Reference: [1] Science, 2017, vol. 358, # 6361, p. 326 - 332
[2] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 245 - 252
[3] Farmaco, 1991, vol. 46, # 7-8, p. 861 - 872
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3592 - 3602
[5] Chirality, 2018, vol. 30, # 7, p. 900 - 906
[6] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 7, p. 1339 - 1347
[7] Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2085 - 2092
[8] Molecules, 2014, vol. 19, # 12, p. 21386 - 21397
[9] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 554 - 569
[10] Green Chemistry, 2017, vol. 19, # 2, p. 474 - 480
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  • [ 149-73-5 ]
  • [ 27798-60-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 235 - 242
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  • [ 149-73-5 ]
  • [ 57486-68-7 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 235 - 242
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  • [ 89368-12-7 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 12, p. 2091 - 2098
  • 9
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  • [ 34589-97-4 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2017, vol. 38, # 12, p. 1481 - 1485