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[ CAS No. 488-93-7 ] {[proInfo.proName]}

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Chemical Structure| 488-93-7
Chemical Structure| 488-93-7
Structure of 488-93-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 488-93-7 ]

CAS No. :488-93-7 MDL No. :MFCD00005350
Formula : C5H4O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IHCCAYCGZOLTEU-UHFFFAOYSA-N
M.W : 112.08 Pubchem ID :10268
Synonyms :
3-Furoic Acid

Calculated chemistry of [ 488-93-7 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 25.67
TPSA : 50.44 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : 1.03
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.36
Log Po/w (SILICOS-IT) : 0.69
Consensus Log Po/w : 0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.58
Solubility : 2.95 mg/ml ; 0.0263 mol/l
Class : Very soluble
Log S (Ali) : -1.68
Solubility : 2.35 mg/ml ; 0.0209 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.92
Solubility : 13.4 mg/ml ; 0.119 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.17

Safety of [ 488-93-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 488-93-7 ]

* 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 [ 488-93-7 ]
  • Downstream synthetic route of [ 488-93-7 ]

[ 488-93-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 488-93-7 ]
  • [ 4412-91-3 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 1.2, p. 131 - 134[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 1, p. 144 - 147
[3] Journal of the American Chemical Society, 2017, vol. 139, # 26, p. 8788 - 8791
[4] Tetrahedron Letters, 1994, vol. 35, # 40, p. 7401 - 7404
[5] Tetrahedron, 1996, vol. 52, # 37, p. 12137 - 12158
[6] Chemical Communications, 2004, # 1, p. 44 - 45
[7] Journal of the American Chemical Society, 1981, vol. 103, # 11, p. 3112 - 3120
[8] Organic and Biomolecular Chemistry, 2006, vol. 4, # 6, p. 1020 - 1031
[9] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
[10] Journal of the American Chemical Society, 1950, vol. 72, p. 2195,2198
[11] Australian Journal of Chemistry, 1989, vol. 42, # 12, p. 2181 - 2190
[12] Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 1989, vol. 43, # 4, p. 381 - 385
[13] Tetrahedron Asymmetry, 2014, vol. 25, # 8, p. 677 - 689
  • 2
  • [ 488-93-7 ]
  • [ 4412-91-3 ]
  • [ 30614-67-6 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 48, p. 9982 - 9998,17
[2] Tetrahedron, 2012, vol. 68, # 48, p. 9982 - 9998
  • 3
  • [ 488-93-7 ]
  • [ 89364-31-8 ]
Reference: [1] Helvetica Chimica Acta, 2003, vol. 86, # 5, p. 1371 - 1396
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 4093 - 4102
[3] Yakugaku Zasshi, 1957, vol. 77, p. 232,234[4] Chem.Abstr., 1957, p. 11344
[5] Tetrahedron, 1981, vol. 37, p. 781 - 787
[6] Farmaco, Edizione Scientifica, 1984, vol. 39, # 3, p. 171 - 188
  • 4
  • [ 488-93-7 ]
  • [ 89364-31-8 ]
  • [ 1679-47-6 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3905,3907
  • 5
  • [ 488-93-7 ]
  • [ 4412-96-8 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 2195,2198
  • 6
  • [ 488-93-7 ]
  • [ 36878-91-8 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 3667,3670
  • 7
  • [ 488-93-7 ]
  • [ 75-65-0 ]
  • [ 56267-48-2 ]
YieldReaction ConditionsOperation in experiment
78% With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; Reflux e. To a solution of 3-furoic acid 96 (54.4 g, 485 mmol), triethylamine (105 ml, 753 mmol), tert-butanol (25.2 mL, 786 mmol) in toluene (800 mL) was added dropwise at room temperature over 45 min period diphenyl phosphoryl azide (157.8 mL, 732 mmol). The resulting solution was heated at reflux for 6 h and at room temperature overnight. The reaction was diluted with water (1000 mL) and extracted twice with ethyl acetate (1000 ml). The organic layers were combined washed with water (800 mL), brine (800 mL), decolorized with activated charcoal, dried, filtered and concentrated in vacuo to furnish a brown semisolid. The semisolid was crystallized from dichloromethane (300 mL) and hexanes (600 mL) to furnish tert-butyl furan-3-ylcarbamate 97 (61.5 g, 78percent). 1H NMR (300 MHz, CDC13) δ 7.71 (s, IH), 7.30 - 7.24 (m, IH), 6.43 (s, IH), 6.27 (s, IH), 1.75 - 1.32 (s, 9H).
76%
Stage #1: for 18 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In water at 0℃; for 2 h;
3-Furoic acid (5.60 g, 1.0 eq) was dissolved in tert-butanol (200 ml) and treated with triethylamine (10 ml, 1.4 eq) and diphenyl phosphoryl azide (12 ml, 1.1 eq).
Mixture was heated at reflux for 18 h.
Reaction mixture was cooled to room temperature, then concentrated to 50 ml and poured into saturated aq. NaHCO3.
Mixture was stirred at 0° C. for 2 h.
Solid was collected by filtration and dried under high vacuum.
The crude reaction mixture was purified by flash chromatography to yield tert-butyl furan-3-ylcarbamate (6.95 g, 76percent): 1H NMR (CDCl3, 400 MHz) δ 7.71 (bs, 1H), 7.27 (m, 1H), 6.27 (bs, 1H), 6.20 (bs, 1H), 1.50 (s, 9H); MS (Q1) 184 (M)+.
76%
Stage #1: for 18 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In water at 0℃; for 2 h;
3-Furoic acid (5.6Og, 1.0 eq) was dissolved in fert-butanol (200 ml) and treated with triethylamine (10 ml, 1.4 eq) and diphenyl phosphoryl azide (12 ml, 1.1 eq). Mixture was heated at reflux for 18 h. Reaction mixture was cooled to room temperature, then concentrated to 50 ml and poured into saturated aq. NaHCO3. Mixture was stirred at 0 °C for 2 h. Solid was collected by filtration and dried under high vacuum. The crude reaction mixture was purified by flash chromatography to yield tert-butyl furan-3-ylcarbamate 32 (6.95 g, 76percent) : 1H NMR (CDCl3, 400 MHz) δ 7.71 (bs, IH), 7.27 (m, IH), 6.27 (bs, IH), <n="139"/>6.20 (bs, IH), 1.50 (s, 9H) ; MS (Ql) 184 (M)+.
76%
Stage #1: for 18 h; Heating / reflux
Stage #2: at 0℃; for 2 h;
3-Furoic acid (5.6Og, 1.0 eq) was dissolved in tert-butanol (200 ml) and treated with triethylamine (10 ml, 1.4 eq) and diphenyl phosphoryl azide (12 ml, 1.1 eq). Mixture was heated at reflux for 18 h. Reaction mixture was cooled to room temperature, then concentrated to 50 ml and poured into saturated aq. NaHCO3. Mixture was stirred at 0 0C for 2 h. Solid was collected by filtration and dried under high vacuum. The crude reaction mixture was purified by flash chromatography to yield tert-butyl furan-3-ylcarbamate 32 (6.95 g, 76percent) : 1H NMR (CDCl3, 400 MHz) δ 7.71 (bs, IH), 7.27 (m, IH), 6.27 (bs, IH), 6.20 (bs, IH), 1.50 (s, 9H) ; MS (Ql) 184 (M)+.
71% With diphenyl phosphoryl azide; triethylamine In toluene for 6 h; Heating / reflux Diphenylphosphoryl azide (78.9 mL) was added dropwise to a solution of 3-furoic acid (Aldrich) (27.2 g) in a mixture of toluene (400 mL), triethylamine (52.5 [ML)] and tert- butanol (35.1 [ML).] The solution was heated to reflux for 6 hours, cooled overnight and water added (500 mL). The mixture was extracted into EtOAc (3 x 500 mL) and the combined organics washed with water [(400 ML), BRINE] (400 mL), decolourised over activated charcoal, dried [(MGS04),] and the solvent removed to give 73 g of a brownish solid. Trituration with 1: 1 [DCM/ISOHEXANE] gave the title compound as a white solid (31.5 g, 71percent) ; [1H] NMR [(CDC13)] [8 1.] 50 (s, 9H), 6.22 (s, br, 1H), 6.27 (s, 1H), 7.26 (d, 1H), 7.69 (s, br, [1H)] ; MS [M/E] [MU 184.]
70% at 90℃; for 12 h; 3-Furoic acid (2.8 g, 25 mmoL), diphenyl azidophosphate (6 ml, 27.5 mmoL) and triethylamine (5 mL, 35 mmoL) were added to tert-butanol (50 mL). The mixture was heated to 90° C. and stirred for 12 hours. After cooled to room temperature, aqueous sodium dicarbonate (2 N, 100 mL) was added. The mixture was filtrated, the filter cake was dissolved in ethyl acetate (100 mL), and washed with water (50 mL×3) and saturated brine (50 mL) in sequence, dried over anhydrous sodium sulfate, then filtrated, the filtrate was concentrated under reduced pressure. The residue was purified by silica column chromatography (petroleum ether:ethyl acetate=10:1) to give white solid 30-h (3.2 g, yield: 70percent). LC-MS (ESI): m/z=184 [M+H]+.
54% for 17 h; Heating / reflux To a solution of 3-furoic acid (5.0 g, 44.61 mmol) in f-butanol (178 mL) were added diphenylphosphoryl azide (10.7 mL, 49.65 mmol) and triethylamine (8.9 mL, 63.85 mmol) and the mixture heated at reflux for 17 h. The resulting dark solution was cooled to RT, concentrated in vacuo to ~ 50 mL, then poured into an aqueous sat. solution OfNaHCO3 at 0 °C and stirred for 2 h. The resulting precipitate was collected by filtration, washed with a little water, then air dried. The resultant tan solid was purified by column chromatography to give the title compound as a white solid (4.4 g, 54 percent). [M + H]+ 184.0

Reference: [1] Patent: WO2010/14930, 2010, A2, . Location in patent: Page/Page column 39
[2] Patent: US2008/76758, 2008, A1, . Location in patent: Page/Page column 77
[3] Patent: WO2008/70740, 2008, A1, . Location in patent: Page/Page column 136-137
[4] Patent: WO2008/73785, 2008, A2, . Location in patent: Page/Page column 163
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
[6] Monatshefte fur Chemie, 2009, vol. 140, # 11, p. 1349 - 1359
[7] Patent: WO2004/13141, 2004, A1, . Location in patent: Page 131
[8] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0240; 0241
[9] Patent: WO2008/152394, 2008, A1, . Location in patent: Page/Page column 25; 32-33
[10] Tetrahedron, 1982, vol. 38, # 18, p. 2783 - 2786
  • 8
  • [ 488-93-7 ]
  • [ 124391-75-9 ]
Reference: [1] Farmaco, Edizione Scientifica, 1984, vol. 39, # 3, p. 171 - 188
[2] Tetrahedron, 1981, vol. 37, p. 781 - 787
[3] ACS Catalysis, 2018, vol. 8, # 2, p. 785 - 789
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