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[ CAS No. 326-90-9 ] {[proInfo.proName]}

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Chemical Structure| 326-90-9
Chemical Structure| 326-90-9
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Product Details of [ 326-90-9 ]

CAS No. :326-90-9 MDL No. :MFCD00020935
Formula : C8H5F3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :OWLPCALGCHDBCN-UHFFFAOYSA-N
M.W : 206.12 Pubchem ID :67594
Synonyms :

Calculated chemistry of [ 326-90-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.91
TPSA : 47.28 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) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.08
Log Po/w (XLOGP3) : 1.49
Log Po/w (WLOGP) : 3.24
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : 2.39
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.81 mg/ml ; 0.00877 mol/l
Class : Soluble
Log S (Ali) : -2.09
Solubility : 1.67 mg/ml ; 0.00812 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.322 mg/ml ; 0.00156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.23

Safety of [ 326-90-9 ]

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

Application In Synthesis of [ 326-90-9 ]

* 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 [ 326-90-9 ]
  • Downstream synthetic route of [ 326-90-9 ]

[ 326-90-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1192-62-7 ]
  • [ 383-63-1 ]
  • [ 326-90-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃;
Stage #2: With hydrogenchloride In water; ethyl acetate
Into a 500 mL flask was weighed 20.0 g (181.6 mmol) of 2-acetylfuran, 50 mL of THF, and 24 mL of ethyl trifluoroacetate. The resulting solution was cooled to 0-3 °C in an ice bath and 1.0 M LiHMDS was added (200 mL). The reaction was allowed to warm to room temperature where it remained overnight. The reaction was then concentrated in vacuo to remove THF and the residue was washed into a separatory funnel with ethyl acetate and 1.0 M HCl. The ethyl acetate was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The resulting 4,4,4-trifluoro-1-furan-2-yl-butane-1,3-dione was recovered as a brown semisolid, yield: 32.5 g (100+percent).
82.6% With sodium In ethanol at 20℃; General procedure: Ethyl trifluoroacetate 9 (0.047 mol) and 2-acetyl furan (0.047 mol) were added dropwise to a solution of ethanol (55 mL) containing thinly sliced sodium (0.047 mol), and stirred over night at room temperature. Then,the solution was poured in ice-water containing concentrated sulfuric acid. The solution was extracted with dichloromethane, dried, concentrated and purified on a column of silica using a 10percent gradient of ethyl acetate in hexanes to afford 10 (82.6percenty). 10(0.020 mmol) was added drop wise into a solution of hydrazinobenzene(0.020 mmol), ethanol(50ml)and acetic acid(0.5 ml), then refluxed.The cooled mixture was concentrated under vacumm and the pyrazole11(66.7percenty) was obtained after purification by silicagel(a5percentgradient of ethyl acetate in hexanes). Pyrazole 11(0.043mol) was dissolved in acetone (120 ml) and KMnO4(0. 071mmol) was added. This mixture was heated at 60°C for 3 h and cooled to room temperature.Then isopropyl alcohol was added and stirred at room temperature overnight. The reaction mixture was filtered and concentrated. The residue was dissolved in 1N NaOH, washed and acidified with 2N HCl solution to obtain 12(46.3 percent y).The amide derivatives 13-14 were prepared through acyl chlorides derived from 12. A solution of 12 (0.004mol) in thionyl chloride(10mL) was refluxed for 5 hand then concentrated under vacuum. The crude acylchloride was added dropwise to a cooled solution(0°C) of substituted aniline(0.004mol) and TEA (0.008mol) in dichloromethane (10mL). The mixture was stirred over night at room temperature, and then purified on a column of silica using a gradient of e thyl acetate in hexanes to afford the pure products.
Reference: [1] Patent: WO2008/73825, 2008, A1, . Location in patent: Page/Page column 134
[2] Chinese Chemical Letters, 2016, vol. 27, # 4, p. 566 - 570
[3] Synthesis, 1997, # 11, p. 1321 - 1324
[4] Journal of the American Chemical Society, 1950, vol. 72, p. 2948,2949
[5] Journal of Fluorine Chemistry, 2002, vol. 118, # 1-2, p. 135 - 147
[6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 343 - 346
[7] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 15, p. 5370 - 5383
[8] Journal of Fluorine Chemistry, 2006, vol. 127, # 6, p. 780 - 786
[9] Russian Journal of General Chemistry, 2007, vol. 77, # 10, p. 1732 - 1741
[10] Chemistry of Heterocyclic Compounds, 2008, vol. 44, # 5, p. 606 - 614[11] Khim. Geterotsikl. Soedin., 2008, # 5, p. 765 - 775,11
[12] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1581 - 1588
[13] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3076 - 3080
[14] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 545 - 551
[15] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 911 - 914
  • 2
  • [ 1192-62-7 ]
  • [ 326-90-9 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: With potassium <i>tert</i>-butylate In benzene
Stage #2: at 5 - 20℃; for 16.3333 h;
Stage #3: With sulfuric acid In waterCooling with ice
[00141] Scheme 6: Synthesis of the diketone intermediate 4,4,4-trifluoro- 1 -(furan-2- vDbutane- 1 ,3-dione 19 6 1; [00142] The diketone 19 was synthesized from acetylfuran and trifluoracetate to obtain the 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione 19 product as follows. 2- Acetylfuran 18 (11.0 g, 210 mmol) was dissolved in benzene (210 mL). At room temperature was added KOtBu (23.6 g, 210 mol). The resulting red solution was cooled to 5° C. Ethyl trifluoracetate 6 (25 mL, 29.8 g, 210 mmol) was added dropwise in approximately 20 minutes keeping the temperature below 15 °C. Then the mixture was stirred for 16 hours at room temperature. The mixture was poured in ice- water (300 mL) containing concentrated sulfuric acid (5 g). The aqueous mixture was extracted with tBME (3 x 200 mL). The combined organic layers were washed with brine (200 mL), dried (Na2SO4) and concentrated to give a dark brown oil (20.8 g). The crude product was purified by kugelrohr distillation to give compound 19 (17.0 g, 39percent) as a yellowish oil.
Reference: [1] Patent: WO2010/96115, 2010, A1, . Location in patent: Page/Page column 55-56
  • 3
  • [ 123826-63-1 ]
  • [ 407-25-0 ]
  • [ 326-90-9 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 48, p. 8701 - 8705
  • 4
  • [ 123826-63-1 ]
  • [ 407-25-0 ]
  • [ 326-90-9 ]
  • [ 910136-44-6 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 48, p. 8701 - 8705
  • 5
  • [ 1192-62-7 ]
  • [ 407-38-5 ]
  • [ 326-90-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 402 - 409
  • 6
  • [ 326-90-9 ]
  • [ 438450-39-6 ]
Reference: [1] Chinese Chemical Letters, 2018, vol. 29, # 6, p. 911 - 914
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