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Chemical Structure| 1479-24-9
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Product Details of [ 1479-24-9 ]

CAS No. :1479-24-9 MDL No. :MFCD00000321
Formula : C11H11FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YMUNUVJSNWUWDA-UHFFFAOYSA-N
M.W : 210.20 Pubchem ID :296342
Synonyms :

Calculated chemistry of [ 1479-24-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.3
TPSA : 43.37 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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.38
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 2.74
Consensus Log Po/w : 2.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.938 mg/ml ; 0.00446 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.655 mg/ml ; 0.00312 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.52
Solubility : 0.0638 mg/ml ; 0.000303 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 1479-24-9 ]

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 [ 1479-24-9 ]

* 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 [ 1479-24-9 ]
  • Downstream synthetic route of [ 1479-24-9 ]

[ 1479-24-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 6148-64-7 ]
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With triethylamine; magnesium chloride In acetonitrile at 20℃; for 0.5 h;
Stage #2: With triethylamine In acetonitrile at 20℃;
Experimental operation: Take malonate potassium salt 1.00 g (about 5.47mmol) of anhydrous magnesium chloride and 0.65 g (About 6.84mmol) in 25 mLround bottom flask was added dropwise 0.55 g of triethylamine was added after 6mL of acetonitrile was dissolved, stirred 30 min at room temperature. Thendropped by 2 mL of acetonitrile was dissolved 0.48 g (2.5 mmol) o-fluorobenzoyl chloride ld, supplemented triethylamine 0.06 mL, stirred atroom temperature overnight. After treatment: 30 mL of water was added to dilutethe reaction solution, and then were added 30,20,20 mL ethyl acetate, and theethyl acetate layer was collected. After 30 mL with saturated brine ethylacetate layer was dried over anhydrous sodium sulfate, and spin dry columnchromatography (PE: EA = 15: 1) to give the product isolated 2d, in 92percent yield.
13.5 g
Stage #1: With triethylamine; magnesium chloride In tetrahydrofuran at 10 - 35℃; for 8.5 h;
Stage #2: at 15 - 35℃; for 16 h;
Example-12: Preparation of compound of Formula Xlla. 2-fluorobenzoic acid (lOg) toluene (80ml) and dimethyl formamide (0.1ml) were charged into a round bottom flask at 25-35°C. To the reaction mass thionyl chloride (12.7g) was added slowly over a period of 30min at same temperature. Reaction mass was heated to reflux and stirred for 3-4hr. After completion of the reaction, reaction mass was cooled to 55-65°C and distilled completely under vacuum at 55-65°C and co-distilled with toluene (2x20ml) to obtain residue and the residue was dissolved in tetrahydrofuran (50ml). Tetrahydrofuran (150ml) and magnesium chloride (24.5g) was added in another round bottom flask at 25-35°C. Reaction mass was cooled to 10-15°C and was added potassium salt of monoethylmalonate (36.4g) at same temperature. To the reaction mass was added triethyl amine (21.6g) slowly over a period of 30min and reaction mass was heated to 25- 35 °C and stirred for 8hr at same temperature. To the reaction mass was added above pre dissolved tetrahydrofuran solution of 2-fluorobenzoyl chloride at 15-25°C and stirred for 16hr at 25-35°C. After completion of the reaction, reaction mass was distilled completely under vacuum at below 50°C and cooled to 25-35°C. To the resultant reaction mass was added water (400ml) and stirred for 3hr at same temperature. Filtered the precipitated solids and washed with water (10ml). The obtained solids were stirred with water (200ml), and a mixture of water (100ml) and sodium bicarbonate (50g), a mixture of water (100ml) and hydrochloric acid (10ml) sequentially at 25-35°C and filtered the solid and washed with water (10ml). The obtained solid was stirred with methanol (20ml) for 40min at 25-35°C. Filtered the solids and washed with methanol (10ml) and dryed the material to obtain title compound. Yield: 13.5 g.
Reference: [1] Patent: CN105663112, 2016, A, . Location in patent: Page/Page column 15
[2] Patent: WO2017/37672, 2017, A1, . Location in patent: Page/Page column 49; 50
  • 2
  • [ 394-47-8 ]
  • [ 1479-24-9 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 0 - 25℃; for 46 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20 - 25℃; for 1 h;
Under nitrogen atmosphere, 30 ML of THF was added to 6.09 g (10 mmol, 1.0 equivalent) of (BrZnCH2COOEt*THF)2..
Under argon atmosphere, a solution of 1.21 g (10 mmol) of 2-fluorobenzonitrile in 5 ML of THF was added dropwise while stirring at 0.similar.5°C.
The mixture was stirred at 20°C.similar.25°C for 46 hours. 15 ML of 10percent hydrochloric acid added dropwise at 20°C or lower, and the mixture was stirred at 20.similar.25°C for 1 hour, followed by dilution with 50 ML of ethyl acetate..
Then, the layers were separated.
The organic layer was washed successively with 15 ML of 1N hydrochloric acid, 20 ML of an aqueous saturated sodium chloride solution, 20 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 20 ML of an aqueous saturated sodium chloride solution..
After washing, the organic layer was dried with anhydrous magnesium sulfate..
Concentration under reduced pressure afforded 1.94 g of the desired product (yield 92percent).1H NMR (CDCl3), (ppm): δ [1.26 (t, J=7.1 Hz), 1.34 (t,J=7.1 Hz)] (3H), [3. 98 (s), 5.84 (s), 12.6 (s)] (2H), 4.17-4.28 (2H, m), 7.08-7.97 (4H, m).
Reference: [1] Patent: EP1471056, 2004, A1, . Location in patent: Page 45-46
  • 3
  • [ 445-27-2 ]
  • [ 105-58-8 ]
  • [ 1479-24-9 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydride In toluene; mineral oil General procedure: The substrate b-ketoesters 10 a–n were either purchased or synthesized following published procedures. Some benzoylacetates were commercially available. Ethyl 3-oxo-3-phenyl propanoate (10a) was purchased. The reaction of benzoylacetates 10 b–n was prepared as described in previous reports. 25–27 A solution of a substituted acetophenone 8 a–n (0.05 mol) dissolved in toluene (50 mL) was added dropwise to a solution containing diethyl carbonate (9) (0.10 mol) and sodium hydride (0.15 mol 60percent dispersion in mineral oil). The mixture was stirred at room temperature, and then refluxed for 30 min. The mixture was poured into ice water,acidified with glacial acetic acid, and extracted with EtOAc (3x100 mL). The EtOAc extract was then dried over anhydrous MgSO4. After removal of the solvent in vacuo, the crude products were purified by silica gel column chromatography eluting with dichloromethane to afford benzoylacetates 10 b–n. All synthetic compounds were in agreement with 1H NMR, 13C NMR, IR and mass spectroscopic data.
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5064 - 5075
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3656 - 3660
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 3922 - 3946
[4] Chemical Communications, 2017, vol. 53, # 58, p. 8136 - 8139
  • 4
  • [ 64-17-5 ]
  • [ 223679-79-6 ]
  • [ 1479-24-9 ]
YieldReaction ConditionsOperation in experiment
85% at 80℃; for 5 h; General procedure: A mixture of an appropriate dione (9a or 9b) (0.3 mol) and EtOH (500 mL) was heated to 80 °C refluxing for 5 h. Upon cooling to room temperature, evaporated the solvent to give the esters 10a or 10b as red oil. 7.10.1
Ethyl 3-(2-fluorophenyl)-3-oxopropanoate (10a)
Red oil; yield: 85percent; MS m/z (ESI): 233.1 [M+Na]+, 443.1 [2M+Na]+.
78% for 10 h; Reflux Step K
Ethyl 3-(2-fluorophenyl)-3-oxopropanoate (Intermediate c)
To a mixture of 400 mL of ethyl alcohol and 200 mL of toluene were added 80g of intermediate b.The reaction mixture was refluxed for 10 h.
After completion of the reaction, the solvent was distilled off under reduced pressure to give black liquid 50 g. Yield: 78percent.
78% for 10 h; Reflux To a mixture of 400 mL of ethyl alcohol and 200 mL of toluene were added 80 g of intermediate b.
The reaction mixture was refluxed for 10 h.
After completion of the reaction, the solvent was distilled off under reduced pressure to give black liquid 50 g. Yield: 78percent.
7 g at 25℃; Reflux Example-7: Preparation of compound of Formula Xlla. Compound of Formula XIa (lOg) and ethanol (50ml) were charged into a round bottom flask at 25-35°C. Reaction mass was heated to reflux and stirred for 2-3hr at and temperature. After completion of the reaction, reaction mass was distilled completely under vacuum at below 50°C and co-distilled with heptane. The resultant reaction mass was stirred with heptane (25ml) for 30min. Filtered the obtained solids and dryed the material to obtain title compound. Yield: 7.0 g; 1H NMR (CDC13): 58.0 (m, 1H), 57.6 (m, 1H), 57.2 (m, 1H), 57.1 (m, 1H), 53.7 (m, 2H), 53.6 (s, 2H), 51.1 (s, 3H); ESI MS: 211 m/z (MH+).

Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2843 - 2855
[2] Archiv der Pharmazie, 2013, vol. 346, # 7, p. 521 - 533
[3] Patent: EP2799437, 2014, A1, . Location in patent: Paragraph 0057
[4] Patent: US2014/364431, 2014, A1, . Location in patent: Paragraph 0188
[5] Patent: WO2017/37672, 2017, A1, . Location in patent: Page/Page column 48
  • 5
  • [ 64-17-5 ]
  • [ 1479-24-9 ]
YieldReaction ConditionsOperation in experiment
52% at 90℃; for 24 h; Reflux The product formed was mixed with ethanol in toluene and heated at 90 C by using reflux condenser for approximately 24 h. The excess ethanol and solvents were removed and progress of reaction was checked by TLC [20]. The final product EFBA was obtained with 52percent yield.
Reference: [1] Journal of Fluorine Chemistry, 2016, vol. 181, p. 36 - 44
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 20, p. 9349 - 9358
  • 6
  • [ 1071-46-1 ]
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 3, p. 620 - 625
  • 7
  • [ 445-29-4 ]
  • [ 1479-24-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2843 - 2855
[2] Archiv der Pharmazie, 2013, vol. 346, # 7, p. 521 - 533
[3] Patent: EP2799437, 2014, A1,
[4] Patent: US2014/364431, 2014, A1,
[5] Patent: WO2017/37672, 2017, A1,
[6] Patent: WO2017/37672, 2017, A1,
  • 8
  • [ 393-52-2 ]
  • [ 1479-24-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2843 - 2855
[2] Archiv der Pharmazie, 2013, vol. 346, # 7, p. 521 - 533
[3] Patent: EP2799437, 2014, A1,
[4] Patent: US2014/364431, 2014, A1,
  • 9
  • [ 6148-64-7 ]
  • [ 445-29-4 ]
  • [ 1479-24-9 ]
Reference: [1] RSC Advances, 2018, vol. 8, # 27, p. 15009 - 15020
  • 10
  • [ 446-52-6 ]
  • [ 1479-24-9 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 31, p. 12616 - 12620
  • 11
  • [ 35227-78-2 ]
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Reference: [1] Synthesis, 1983, # 1, p. 52 - 53
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