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[ CAS No. 1192-62-7 ] {[proInfo.proName]}

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Product Details of [ 1192-62-7 ]

CAS No. :1192-62-7 MDL No. :MFCD00003242
Formula : C6H6O2 Boiling Point : -
Linear Structure Formula :C4H3O(COCH3) InChI Key :IEMMBWWQXVXBEU-UHFFFAOYSA-N
M.W : 110.11 Pubchem ID :14505
Synonyms :
2-Furyl methyl ketone
Chemical Name :1-(Furan-2-yl)ethanone

Calculated chemistry of [ 1192-62-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 28.9
TPSA : 30.21 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 0.52
Log Po/w (WLOGP) : 1.48
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.25
Solubility : 6.24 mg/ml ; 0.0567 mol/l
Class : Very soluble
Log S (Ali) : -0.73
Solubility : 20.7 mg/ml ; 0.188 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.88
Solubility : 1.44 mg/ml ; 0.0131 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 1192-62-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P264-P280-P302+P352+P312-P304+P340+P310-P305+P351+P338 UN#:2811
Hazard Statements:H300+H330-H311-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1192-62-7 ]

* 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 [ 1192-62-7 ]
  • Downstream synthetic route of [ 1192-62-7 ]

[ 1192-62-7 ] Synthesis Path-Upstream   1~17

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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 5, p. 3116 - 3124
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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 5, p. 3116 - 3124
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Reference: [1] Angewandte Chemie, 1994, vol. 106, # 21, p. 2275 - 2276
[2] Tetrahedron Letters, 1988, vol. 29, # 48, p. 6227 - 6230
[3] Helvetica Chimica Acta, 1932, vol. 15, p. 1118,1121
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  • [ 28588-74-1 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 5, p. 3116 - 3124
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YieldReaction ConditionsOperation in experiment
61% With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring.
The reaction mixture was stirred overnight, then poured onto cold water.
The product was extracted with ether (200 mL, 3* times).
Yield 61percent, mp 92-93° C. (hexanes/ether, Lit. mp 94-95° C.; see Gilman H., et al., J. Am. Chem. Soc., 53, 4192-4196 (1931).
1H NMR (CDCl3); δ 2.45 (s, 3H), 6.49 (d, J=3.9 Hz, 1H), 7.12 (d, J=3.6 Hz, 1H).
13C NMR; δ 8185.4, 154.4, 128.2, 118.9,114.3, 25.7.
50.4% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 24 h; To a solution of 1 (10 g, 90 mmol) in DMF 40 mL, NBS (19g, 108 mmol) was added by keeping the temperature at 0 °C. Thereaction mixture was stirred overnight at room temperature. Upon completion,the reaction mixture was poured into ice-cold water. The mixture was dilutedwith EtOAc, and the insoluble material was filtered off through Celite. Theorganic layer of the filtrate was washed with brine, dried anhydrous magnesiumsulfate, and concentrated. The residue was chromatographed (SiO2,EtOAc/n-hexane, 1/19, v/v) to afford compound 2 (8.7 g, 45.4mmol, 50.4percent). 1H NMR (500 MHz, CDCl3,δ, ppm): 2.46 (3H. s),6.49 (1H, d, J = 3.4 Hz), 7.12 (1H,d, J = 3.4 Hz). MS m/z 188 (M + H)+.
44.5% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.5 h; Synthesis of 2-acetyl-5-bromofuran (29)
2-Acetylfuran (2.2 g, 20 mmol) was dissolved in DMF (20 mL), followed by addition of N-bromosuccinimide (3.91 g, 22 mmol).
The mixture was reacted at room temperature for 30 min and then added into distilled water (50 mL), and the layers were separated with ethyl acetate (50 mL x 2).
The ethyl acetate layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/15) as an elution solvent to obtain Compound 29.
Yield 1.68 g (yield rate 44.5percent).
44.5% With N-Bromosuccinimide In hexane; water; ethyl acetate; N,N-dimethyl-formamide Synthesis of 2-acetyl-5-bromofuran (29)
2-Acetylfuran (2.2 g, 20 mmol) was dissolved in DMF (20 mL), followed by addition of N-bromosuccinimide (3.91 g, 22 mmol).
The mixture was reacted at room temperature for 30 min and then added into distilled water (50 mL), and the layers were separated with ethyl acetate (50 mL*2).
The ethyl acetate layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/15) as an elution solvent to obtain Compound 29.
Yield 1.68 g (yield rate 44.5percent).
28% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; To a stirred solution of compound 4 (5.0 g, 45.45 mmol) and DMF (50 mL), NBS (8.8 g, 50 mmol) was added portion-wise at room temperature under stirring. The reaction mixture was allowed to stir at room temperature overnight. 50percent starting material remained by TLC and LCMS. Reaction mixture was poured into cold water and the compound was extracted with diethyl ether (150 mL X 3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 5percent ethyl acetate in n-hexane as an eluent to afford compound 43 (2.4 g, 28percent) as a white solid.

Reference: [1] Journal of Natural Products, 2017, vol. 80, # 9, p. 2561 - 2565
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 14, p. 3658 - 3664
[3] Patent: US2005/282853, 2005, A1, . Location in patent: Page/Page column 15; 19
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 7, p. 1784 - 1788
[5] Organic Letters, 2017, vol. 19, # 21, p. 5976 - 5979
[6] Patent: EP2030635, 2009, A1, . Location in patent: Page/Page column 26; 50
[7] Patent: US2010/278733, 2010, A1,
[8] Patent: WO2013/130892, 2013, A1, . Location in patent: Paragraph 00287
[9] Patent: US2010/29745, 2010, A1, . Location in patent: Page/Page column 14
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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
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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
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Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 402 - 409
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Reference: [1] Gazzetta Chimica Italiana, 1958, vol. 88, p. 879,896
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Reference: [1] Patent: US4374988, 1983, A,
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Reference: [1] Carbohydrate Research, 1997, vol. 305, # 1, p. 1 - 15
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Reference: [1] Carbohydrate Research, 1997, vol. 305, # 1, p. 1 - 15
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 12, p. 2341 - 2345[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 12, p. 2610 - 2614
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YieldReaction ConditionsOperation in experiment
97% at 100℃; for 9 h; A mixture of 2-acetylfuran (25.0 g, 0.227 mmol) and N,N-dimethylformamide dimethylacetal (40 ml) was stirred at 100°C for 9 hours. After cooling as it was, the reaction mixture was concentrated. To the residue were added diethyl ether and hexane. The resulting solid was collected by filtration and washed with hexane, to give the title compound (36.5 g, 97percent) as a brown solid.1H NMR (400 MHz, DMSO-d6) δ ppm; 2.88 (3H, br s), 3.14 (3H, br s), 5.65 (1H, d, J= 12.6 Hz), 6.60 (1H, dd, J=2.0, 3.4 Hz), 7.10 (1H, dd, J = 0.8, 3.4 Hz), 7.68 (1H, d, J = 12.6 Hz), 7.79 (1H, dd, J = 0.8, 2.0 Hz).
97% at 100℃; for 9 h; Reference Example 5
3-(Dimethylamino)-1-(2-furyl)-2-propen-1-one
A mixture of 2-acetylfuran (25.0 g, 0.227 mmol) and N,N-dimethylformamide dimethylacetal (40 ml) was stirred at 100° C. for 9 hours.
After cooling as it was, the reaction solution was concentrated.
Diethyl ether and hexane were added to the residue, and the resulting solid was collected by filtration and washed with hexane, to give the title compound (36.5 g, 97percent) as a brown solid.
1H NMR (400 MHz, DMSO-d6) δ ppm; 2.88 (3H, br s), 3.14 (3H, br s), 5.65 (1H, d, J=12.6 Hz), 6.60 (1H, dd, J=2.0, 3.4 Hz), 7.10 (1H, dd, J=0.8, 3.4 Hz), 7.68 (1H, d, J=12.6 Hz), 7.79 (1H, dd, J=0.8, 2.0 Hz).
Reference: [1] Patent: EP1439175, 2004, A1, . Location in patent: Page 45-46
[2] Patent: US2004/6082, 2004, A1, . Location in patent: Page/Page column 22
[3] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1707 - 1710
[4] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495
[5] Journal of the Korean Chemical Society, 2011, vol. 55, # 2, p. 243 - 250
[6] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1837 - 1843
[7] Journal of the Chinese Chemical Society, 2003, vol. 50, # 2, p. 283 - 296
[8] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 21, p. 6282 - 6285
[9] Synthetic Communications, 2012, vol. 42, # 10, p. 1521 - 1531
[10] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1581 - 1588
[11] Journal of Heterocyclic Chemistry, 2014, vol. 51, # SUPPL. 1, p. E384-E388
[12] Research on Chemical Intermediates, 2015, vol. 41, # 6, p. 3759 - 3765
[13] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 936 - 942
[14] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 545 - 551
[15] Bioorganic Chemistry, 2019, vol. 83, p. 549 - 558
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YieldReaction ConditionsOperation in experiment
168 g at 110℃; for 3 h; 2-acetyl-furan (121 g, 1.1 mol) and N, N- dimethylformamide dimethyl acetal (155 g, 1.3 mol) was dissolved in 500 ml of anhydrous dimethyl formamide, in 110 was refluxed for 3 hours. After the spin-dry solvent, ether was added and the product was precipitated crystals were separated and dried to give 168 g of yellow crystals.
Reference: [1] Patent: CN105237518, 2016, A, . Location in patent: Paragraph 0048
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Reference: [1] Journal of the Chemical Society - Dalton Transactions, 1997, # 21, p. 4025 - 4035
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Reference: [1] Heterocycles, 1998, vol. 47, # 2, p. 689 - 702
[2] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495