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[ CAS No. 174671-46-6 ] {[proInfo.proName]}

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Chemical Structure| 174671-46-6
Chemical Structure| 174671-46-6
Structure of 174671-46-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 174671-46-6 ]

CAS No. :174671-46-6 MDL No. :MFCD10699483
Formula : C7H6BFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LFQDNHWZDQTITF-UHFFFAOYSA-N
M.W : 151.93 Pubchem ID :11499245
Synonyms :
AN-2690

Calculated chemistry of [ 174671-46-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.0
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : 0.31
Log Po/w (MLOGP) : 0.65
Log Po/w (SILICOS-IT) : 0.69
Consensus Log Po/w : 0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.84
Solubility : 2.19 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (Ali) : -1.25
Solubility : 8.56 mg/ml ; 0.0564 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.14
Solubility : 1.11 mg/ml ; 0.00729 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.77

Safety of [ 174671-46-6 ]

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 [ 174671-46-6 ]

* 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 [ 174671-46-6 ]
  • Downstream synthetic route of [ 174671-46-6 ]

[ 174671-46-6 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 845301-93-1 ]
  • [ 174671-46-6 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.833333 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexanes at 20℃; for 1.75 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water at 30℃;
To a solution of 5b (73.2 g, 293 mmol) in dry THF (400 mL) was added n-butyllithium (1.6 M in hexanes; 200 mL) over 45 min at -78° C. under nitrogen atmosphere. Anion precipitated. After 5 min, (i-PrO)3B (76.0 mL, 330 mmol) was added over 10 min, and the mixture was allowed to warm to room temperature over 1.5 h. Water and 6 N HCl (55 mL) were added, and the solvent was removed under reduced pressure to about a half volume. The mixture was poured into ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. To a solution of the residue in tetrahydrofuran (360 mL) was added 6 N HCl (90 mL), and the mixture was stirred at 30° C. overnight. The solvent was removed under reduced pressure to about a half volume. The mixture was poured into ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the residue was treated with i-Pr2O/hexane to give 19b (26.9 g, 60percent) as a white powder: mp 118-120° C.; 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.95 (s, 2H), 7.15 (m, 1H), 7.24 (dd, J=9.7, 1.8 Hz, 1H), 7.74 (dd, J=8.2, 6.2 Hz, 1H), 9.22 (s, 1H); ESI-MS m/z 151 (M-H)-; HPLC purity 97.8percent; Anal (C7H6BFO2) C, H.
Reference: [1] Patent: US2007/265226, 2007, A1, . Location in patent: Page/Page column 59
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450
[3] Patent: US2007/286822, 2007, A1,
  • 2
  • [ 651326-68-0 ]
  • [ 174671-46-6 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.166667 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexanes at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water at 20℃; for 1 h;
Dissolve [1-BROMO-2- (1-ETHOXY-ETHOXYMETHYL)-4-FLUORO-BENZENE] (5.4g, 19.5 mmol) in dry THF (100 mL) and cool to-78 °C under nitrogen. Add butyl lithium (2.5M in Hexanes, 10.2 mL, 25.4 mmol) dropwise at-78 °C. Upon complete addition, stir the reaction at-78 [°C] for 10 minutes and then add trimethyl borate (4.4 mL, 39 mmol) and warm the reaction to room temperature. Pour the reaction into IN [HC1] (100 mL) and stir for 1 hour. Extract the biphasic mixture with ether three times. Dry the combined organic layers with sodium sulfate, filter and concentrate in vacuo. Triturate the oily residue with cold hexanes to yield 2.1 g (70percent) of the title compoud as a white solid NMR (d6- DMSO) [C19.] 18 (s, 1H), 7.70 (dd, J= 8.2, 5.8 Hz, 1H), 7.20 (dd, [J= 9.] 5,2. 7 Hz, 1H), 7.11 (m, 1H), 4.92 (s, 1H).
Reference: [1] Patent: WO2004/9578, 2004, A2, . Location in patent: Page 36-37
  • 3
  • [ 5419-55-6 ]
  • [ 174671-46-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 0.5 h; Inert atmosphere
Stage #2: at 30℃; for 5 h; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 40℃; for 6 h;
(3) Under nitrogen protection, 32.5 g of compound III was added to 250 ml of tetrahydrofuran, and cooled to -70 ° C, 55 ml of n-butyllithium was added dropwise, and the reaction was started for 0.5 h with the addition of n-butyllithium. Sampling liquid phase tracking, adding 39 ml of triisopropyl borate, adding dropwise, heating to 30 ° C, reaction for 5 h, Sampling liquid phase tracking, after completion of the reaction, adding 150 ml of water and 40 mL of 2 mol / l hydrochloric acid, adjusting the pH to 3, layering the organic layer, extracting the aqueous layer with ethyl acetate 3 times each time 50 ml, combining the organic layer, using saturated salt Washed with water, dried over anhydrous sodium sulfate, filtered and evaporated The intermediate was dissolved in 90 ml of tetrahydrofuran, and then added with 23 mL of 6 mol/L HCl, heated to 40 ° C, and reacted for 6 h, extracted with 100 ml of ethyl acetate and 300 ml of water, and the organic layer was separated and the aqueous layer was extracted with ethyl acetate three times each time. 50 ml, the organic layer was combined, washed with saturated brine and concentrated to dryness to give a crude product; Add 50ml of deionized water to the crude product, adjust the pH to 14 with 5percent sodium hydroxide solution, stir the impurities, filter the filtrate, decolorize the filtrate with activated carbon once, add ethyl acetate to elute, take the water layer and add hydrochloric acid. The pH was adjusted to 1, and the solid was precipitated. The organic layer was separated by adding 50 ml of dichloromethane. The aqueous layer was extracted twice with dichloromethane (50 ml), and the organic layer was combined. Dry with anhydrous sodium sulfate and filter. The benzoxaborolane antifungal drug was concentrated under reduced pressure in a yield of 80percent.
Reference: [1] Patent: CN108358961, 2018, A, . Location in patent: Paragraph 0016; 0057; 0058-0060; 0064-0066; 0069; 0073-0075
  • 4
  • [ 1061223-45-7 ]
  • [ 174671-46-6 ]
YieldReaction ConditionsOperation in experiment
81% at 20℃; for 4 h; A mixture of crude (4-fluoro-2-(hydroxymethyl) phenyl)boronic acid (3 g) and 10percent H2S04 solution (20 mL) is stirred at room temperature for 4 hrs. Water is added, and the mixture is extracted with ethyl acetate. The organic layer is washed with brine and dried on anhydrous sodium sulfate. The solvent is removed under reduced pressure, and the residue is treated with MTBE to afford benzo[c] [l,2]oxaborole-l,5(3H)-diol (Yield: 81percent; Purity: 95percent).
Reference: [1] Patent: WO2017/183043, 2017, A1, . Location in patent: Page/Page column 34
  • 5
  • [ 139911-29-8 ]
  • [ 174671-46-6 ]
Reference: [1] Patent: WO2017/125835, 2017, A1, . Location in patent: Paragraph 00117
  • 6
  • [ 943310-56-3 ]
  • [ 174671-46-6 ]
YieldReaction ConditionsOperation in experiment
60% With hydrogenchloride In tetrahydrofuran at 30℃; To a solution of 5b (73.2 g, 293 mmol) in dry THF (400 mL) was added n-butyllithium (1.6 M in hexanes; 200 mL) over 45 min at -78° C. under nitrogen atmosphere.
Anion precipitated.
After 5 min, (i-PrO)3B (76.0 mL, 330 mmol) was added over 10 min, and the mixture was allowed to warm to room temperature over 1.5 h.
Water and 6 N HCl (55 mL) were added, and the solvent was removed under reduced pressure to about a half volume.
The mixture was poured into ethyl acetate and water.
The organic layer was washed with brine and dried over anhydrous Na2SO4.
The solvent was removed under reduced pressure.
To a solution of the residue in tetrahydrofuran (360 mL) was added 6 N HCl (90 mL), and the mixture was stirred at 30° C. overnight.
The solvent was removed under reduced pressure to about a half volume.
The mixture was poured into ethyl acetate and water.
The organic layer was washed with brine and dried over anhydrous Na2SO4.
The solvent was removed under reduced pressure, and the residue was treated with i-Pr2O/hexane to give 19b (26.9 g, 60percent) as a white powder: mp 118-120° C.; 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.95 (s, 2H), 7.15 (m, 1H), 7.24 (dd, J=9.7, 1.8 Hz, 1H), 7.74 (dd, J=8.2, 6.2 Hz, 1H), 9.22 (s, 1H); ESI-MS m/z 151 (M-H)-; HPLC purity 97.8percent; Anal (C7H6BFO2) C, H.
Reference: [1] Patent: US2007/286822, 2007, A1, . Location in patent: Page/Page column 60-61
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450
  • 7
  • [ 5419-55-6 ]
  • [ 202865-66-5 ]
  • [ 174671-46-6 ]
Reference: [1] CrystEngComm, 2014, vol. 16, # 23, p. 4999 - 5011
[2] Tetrahedron, 2007, vol. 63, # 38, p. 9401 - 9405
  • 8
  • [ 202865-66-5 ]
  • [ 174671-46-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7317 - 7322
[3] Patent: WO2017/183043, 2017, A1,
[4] Patent: WO2017/183043, 2017, A1,
[5] Patent: WO2017/183043, 2017, A1,
[6] Patent: WO2017/183043, 2017, A1,
[7] Patent: WO2017/183043, 2017, A1,
[8] Patent: US2007/286822, 2007, A1,
  • 9
  • [ 94569-84-3 ]
  • [ 174671-46-6 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 38, p. 9401 - 9405
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450
[3] Patent: CN108358961, 2018, A,
[4] Patent: US2007/286822, 2007, A1,
  • 10
  • [ 13675-18-8 ]
  • [ 202865-66-5 ]
  • [ 174671-46-6 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
  • 11
  • [ 456-47-3 ]
  • [ 174671-46-6 ]
Reference: [1] Patent: US2007/286822, 2007, A1, . Location in patent: Page/Page column 48
[2] Patent: US2007/286822, 2007, A1, . Location in patent: Page/Page column 48
  • 12
  • [ 7732-18-5 ]
  • [ 174671-46-6 ]
YieldReaction ConditionsOperation in experiment
4.1 g
Stage #1: for 2 h; Reflux
Directly to the next step.The reaction solution containing the compound represented by the formula (III) obtained above is slowly heated to reflux the reaction solution in 5 to 10 minutes,The reaction solution was allowed to react for 2 hours while maintaining the reflux.The reaction solution was poured into about 140 ml of ice water,Stirring,Precipitated as a white solid 4.1 g,The resulting white solid,Mp: 126 to 129 ° C,The structure was confirmed by NMR analysis.
Reference: [1] Patent: CN106467557, 2017, A, . Location in patent: Paragraph 0022; 0034; 0035
  • 13
  • [ 850567-57-6 ]
  • [ 174671-46-6 ]
  • [ 1447933-60-9 ]
  • [ 2357-33-7 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 27, p. 9050 - 9058
  • 14
  • [ 877264-43-2 ]
  • [ 174671-46-6 ]
Reference: [1] Patent: WO2017/183043, 2017, A1,
  • 15
  • [ 452-63-1 ]
  • [ 174671-46-6 ]
Reference: [1] Patent: WO2017/125835, 2017, A1,
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