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[ CAS No. 79418-78-3 ] {[proInfo.proName]}

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Chemical Structure| 79418-78-3
Chemical Structure| 79418-78-3
Structure of 79418-78-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 79418-78-3 ]

CAS No. :79418-78-3 MDL No. :MFCD02683560
Formula : C8H7FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OOGOFUKAJDPHDJ-UHFFFAOYSA-N
M.W : 170.14 Pubchem ID :598452
Synonyms :

Calculated chemistry of [ 79418-78-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.3
TPSA : 46.53 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 1.1
Log Po/w (WLOGP) : 1.77
Log Po/w (MLOGP) : 0.94
Log Po/w (SILICOS-IT) : 1.92
Consensus Log Po/w : 1.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.83
Solubility : 2.54 mg/ml ; 0.0149 mol/l
Class : Very soluble
Log S (Ali) : -1.67
Solubility : 3.64 mg/ml ; 0.0214 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.17
Solubility : 1.14 mg/ml ; 0.00673 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 79418-78-3 ]

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 [ 79418-78-3 ]

* 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 [ 79418-78-3 ]
  • Downstream synthetic route of [ 79418-78-3 ]

[ 79418-78-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 127685-76-1 ]
  • [ 79418-78-3 ]
YieldReaction ConditionsOperation in experiment
89% With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide In ethylene glycol at 80℃; for 6 h; General procedure: a mixture of substrate 1a(1 mmol), cobalt salt (n1molpercent) and NaOH (n2 equiv)in EG (5 mL) was stirred with O2 (1 atm) being bubbled, under 80 oCfor 8 h. Hydrochloric acid (10 mL, 2percent) and methyl tert-butyl ether (MTBE, 10 mL) were successively added to the reactionmixture. The organic layer was separated, and the aqueous phase was furtherextracted with MTBE(10 mL × 2). The combined organic phase was dried over anhydrous sodium sulfateand concentrated to give a residue, which was purified by column chromatographyon silica gel (eluents: petroleum ether/ethyl acetate, 10/1) to provide thedesired products 2a.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 8, p. 1406 - 1411
[2] Green Chemistry, 2014, vol. 16, # 5, p. 2807 - 2814
[3] Green Chemistry, 2014, vol. 16, # 3, p. 1248 - 1254
  • 2
  • [ 1089186-95-7 ]
  • [ 79418-78-3 ]
YieldReaction ConditionsOperation in experiment
72% With hydrogenchloride; hexamethylenetetramine; acetic acid In waterReflux A solution of 25.4 g (74 mmol) 1-(3-fluoro-4-hydroxy-5-methoxyphenyl)-N,N,N-trimethylmethanaminiumiodide was dissolved in acetic acid (65 mL) and H2O (65 mL) and heated to reflux.Hexamethylenetetramine 40 g (285 mmol) was added to the refluxing solution in one portion. The mixture was stirred at reflux for 2 hours at which time concentrated HCl (16.4 mL) was added. Thesolution was stirred an additional 5 minutes, cooled, and extracted with ether (3 X 175 mL). The organiclayer was washed with H2O (2 X 175 mL), dried over MgSO4, and concentrated under vacuum to give9.00 g (72percent yield) of 3a as a white powder. 1H NMR (300 MHz, CDCl3) 9.75 (s, 1H), 7.35 (d, J = 10.3 Hz,1H), 7.31 (s, 1H), 3.88 (s, 3H). 19F NMR (282 MHz, C6D6) -134.71 (d, J = 10.2 Hz)
0.29 g With hexamethylenetetramine In water; acetic acid at 120℃; for 2 h; Commercially available 2-fluoro-6-methoxyphenol (1.00 g, 6.8 mmol) was added to a solution of 40percent dimethylamine (1.6 mL, 12.4 mmol) and 37percent formaldehyde (0.92 mL, 12.4 mmol) in ethanol (20 mL). The mixture was refluxed for 2 h, cooled to room temperature, and concentrated in vacuo to give a solid. The solid was triturated with ether and the solvent was removed under vacuum. The product was dissolved in chloroform (20 mL) and iodomethane (4.0 mL, 64.2 mmol) was added. The reaction mixture was stirred for 18 h at room temperature and filtered. Without purification the filtrate was dissolved in acetic acid (20 mL) and H2O (20 mL) and then HMTA (1.4 g, 10.3 mmol) was added. The reaction mixture was heated to 120 °C. After 2 h, conc. HCl (0.8 mL) was added and it was heated for a further 5 min and cooled. The reaction mixture was extracted with EtOAc and water. The organic layer was dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 7 as a white solid (0.29 g, 25percent).
Reference: [1] Synlett, 2014, vol. 25, # 20, p. 2891 - 2894
[2] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 233 - 243
  • 3
  • [ 73943-41-6 ]
  • [ 76-05-1 ]
  • [ 79418-78-3 ]
  • [ 79418-73-8 ]
YieldReaction ConditionsOperation in experiment
36% at 80℃; for 2.5 h; Hexamethylenetetramine (178 g, 1.27 mmol) was dissolved in trifluoroacetic acid (330 mL), and the solution was heated to 80°C. To the solution was dropwise added a solution of compound ii-15a (90 g, 633 mmol) in trifluoroacetic acid (330 mL) over 1.5 hours. Thereafter, the solution was stirred at 80°C for 1 hour. The reaction liquid was cooled to room temperature, and thereto was added a 20percent aqueous sodium carbonate solution to adjust the pH thereof to 8. Thereafter, a 2 N aqueous hydrochloric acid solution was used to adjust the pH to 4. The liquid was subjected to extraction with ethyl acetate, and then activated carbon and magnesium sulfate were added to the target phase. The solution was subjected to filtration. The solution was concentrated while the residue was subjected to silica chromatography. The resultant desired-compound-containing fraction was concentrated and dried under reduced pressure to yield each of compound ii-15b (38.8 g, yield: 36percent) and compound ii-15c (28.0 g, yield: 26percent).1H-NMR (DMSO-d6) δ: 10.48 (1H, s), 9.77 (1H, s), 7.39 (1H, d, J = 10.2 Hz), 7.34 (1H, s), 3.89 (3H, s).15b1H-NMR (DMSO-d6) δ: 10.02 (1H, s), 9.65 (1H, s), 7.31 (1H, dd, J = 8.1, 8.1 Hz), 6.98 (1H, d, J = 8.1 Hz), 3.90 (3H, s).15c
Reference: [1] Patent: EP2557082, 2013, A1, . Location in patent: Paragraph 0343; 0345
  • 4
  • [ 100-97-0 ]
  • [ 79418-78-3 ]
YieldReaction ConditionsOperation in experiment
46 g With acetic acid In water for 2 h; Reflux To a solution of 146 (124 g, 362 mmol) in FIOAc (300 mL) and water (300 mL) is added HMTA (196 g, 1.4 mol) under reflux. After stirring for 2 hour, concentrated HC1 solution (80 mL) is added and the mixture is stirred for 5 minutes, cooled, and extracted with MTBE (800 rnL x 3). The combined organic layers are washed with water (800 mL x 2), dried over anhydrous magnesium sulfate, and concentrated to give 147 as a white solid (46 g. 75percent yield).
Reference: [1] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0408
  • 5
  • [ 50-00-0 ]
  • [ 73943-41-6 ]
  • [ 79418-78-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 299 - 302
  • 6
  • [ 103905-49-3 ]
  • [ 79418-78-3 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 21, p. 4072 - 4073
[2] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 233 - 243
[3] Synlett, 2014, vol. 25, # 20, p. 2891 - 2894
[4] Patent: WO2017/176812, 2017, A1,
  • 7
  • [ 73943-41-6 ]
  • [ 79418-78-3 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 21, p. 4072 - 4073
[2] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 233 - 243
[3] Synlett, 2014, vol. 25, # 20, p. 2891 - 2894
  • 8
  • [ 456-49-5 ]
  • [ 79418-78-3 ]
Reference: [1] Synlett, 2014, vol. 25, # 20, p. 2891 - 2894
  • 9
  • [ 71144-35-9 ]
  • [ 77-78-1 ]
  • [ 71924-61-3 ]
  • [ 79418-78-3 ]
  • [ 79418-74-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1395 - 1399
[2] Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1395 - 1399
  • 10
  • [ 71144-41-7 ]
  • [ 79418-78-3 ]
  • [ 79418-74-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1395 - 1399
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