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Product Details of [ 6971-51-3 ]

CAS No. :6971-51-3 MDL No. :MFCD00004637
Formula : C8H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IIGNZLVHOZEOPV-UHFFFAOYSA-N
M.W : 138.16 Pubchem ID :81437
Synonyms :

Calculated chemistry of [ 6971-51-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.06
TPSA : 29.46 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) : -9.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : -3.61
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 1.21
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 0.45

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.27
Solubility : 2550.0 mg/ml ; 18.4 mol/l
Class : Highly soluble
Log S (Ali) : 3.58
Solubility : 521000.0 mg/ml ; 3770.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.33
Solubility : 0.654 mg/ml ; 0.00473 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 6971-51-3 ]

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 [ 6971-51-3 ]

* 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 [ 6971-51-3 ]
  • Downstream synthetic route of [ 6971-51-3 ]

[ 6971-51-3 ] Synthesis Path-Upstream   1~69

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  • [ 73279-04-6 ]
Reference: [1] Patent: CN105859654, 2016, A,
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  • [ 1143-70-0 ]
Reference: [1] ChemMedChem, 2011, vol. 6, # 12, p. 2273 - 2286
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YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; triethylamine In dichloromethane at 20℃; for 1 h; 3-methoxybenzyl alcohol (248 μ, 2.0 mmol) and triethylamine (335 μ, 2.4 mmol) were dissolved in anh. DCM (7 mL). Thionyl chloride (218 μ, 3.0 mmol) was added slowly. The reaction mixture was stirred at RT. for 1 h. The reaction mixture was washed with an aqueous solution of HCI 1 N. The organic phase was dried over MgS04. The solvent was removed under reduced pressure to give the desired 2-methoxybenzyl chloride (313 mg, 100 percent) as a yellowish oi l . 4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid (example 74, 85 mg, 0.26 mmol) was dissolved in anhydrous DMF (1 mL) then cesium carbonate (169 mg, 0.52 mmol) and 3-methoxybenzyl chloride (81 mg, 0.52 mmol) were added. The reaction mixture was stirred at r.t. for 18 h. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgS04. The solvent was removed under reduced pressure. Purification of the crude by flash chromatography using a mixture of Cyclohexane/EtOAc (8/2) as eluent gave the desired (3- m e t h o x y p h e n y l ) m e t h y l 4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4- dihydropyridine-5-carboxylate as a yellowish oil (1 1 mg, 9 percent). 1 H N MR (300 MHz, CDCI3) δ 2.62 (s,3H), 2.71 (dd, J = 15.8, 2.2 Hz, 1 H), 2.92 (dd, J = 15.8, 7.5 Hz, 1 H), 3.31 (s, 3H), 3.37 (ddd, J = 10.0, 8.5, 3.6 Hz, 1 H), 3.46 (dt, J = 10.0, 4.1 Hz, 1 H), 3.70-3.79 (m, 4H), 4.13-4.23 (m, 2H), 5.04 (d, J = 12.7 Hz, 1 H), 5.1 1 (d, J = 12.7 Hz, 1 H), 6.64(s, 1 H), 6.70 (d, J = 7.5, 1 H), 6.81 (dd, J = 8.2, 2.5 Hz, 1 H), 7.10 (d, J = 8.4 Hz, 2H), 7.16-7.23 (m,3H). MS [M+H]+ 444. HRMS : calcd for C24H27N05CI, [M+H]+ 444.1578, found 444.1579.
104 g for 1 h; Reflux 100 g of m-methoxybenzyl alcohol was added to 160 ml of thionyl chloride,The mixture was heated to reflux reaction lh. After the reaction, the excess amount of thionyl chloride was recovered under reduced pressure to obtain 104 g of m-methoxybenzyl chloride oil. The purity of GC was 98percent or more.
Reference: [1] Patent: WO2016/16238, 2016, A1, . Location in patent: Page/Page column 126-127
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[24] Patent: US4055574, 1977, A,
[25] Patent: US3947520, 1976, A,
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Reference: [1] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
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  • [ 5071-96-5 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 9, p. 1993 - 1997
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  • [ 5020-41-7 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 42, p. 9832 - 9839
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YieldReaction ConditionsOperation in experiment
96% With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.00833333 h; General procedure: A mixture of the substrate (1 mmol) and the PEG-SANMnanocomposite (8 mg) in methanol (2 mL) was stirred at roomtemperature. After completion of the reaction (monitored byTLC), the catalyst was filtered off and the solvent was evaporatedunder reduced pressure. The crude product was purifiedby column chromatography on silica gel to yield pure alcoholsand phenols.
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[6] Tetrahedron Letters, 2001, vol. 42, # 38, p. 6771 - 6774
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YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate In methanol at 20℃; for 1 h; General procedure: benzaldehyde derivatives (1 mmol) in methanol (15 mL), sodium borohydride (2 mmol) and stirred at room temperature for 1 h. Usual work-up, quantitative yield.
98% With hydrogen In methanol at 20℃; for 4.7 h; General procedure: A mixture of 1a (196 mg, 1 mmol) and 1percentPd/Ni bimetallic catalyst9 (60 mg, 30 wt percent) in MeOH (10 mL) was stirred underH2 at room temperature and atmospheric pressure (on an atmosphericpressure hydrogenation apparatus) until the absorption of hydrogen ceased(3.5 h). After the catalyst was removed off by a magnetic stirring bar, thesolution was evaporated in a vaporator to give the product 2a
95% With sodium benzoate; sodium tetrahydroborate; acetophenone In water at 20℃; for 1.41667 h; Sonication; Green chemistry General procedure: In a round-bottomed flask (10 ml) equipped with a magnetic stirrer, a solution of benzaldehyde (0.106 g, l mmol) and acetophenone (0.120 g, 1 mmol) in H2O (3 mL) was prepared. To this solution, NaBH4(0.047 g, 1.25 mmol) and PhCO2Na (0.138 g, 2 mmol) was added. The mixture was stirred and irradiated with ultrasound waves at room temperature for 60 minutes. TLC monitored the progress of reaction. After 60 min, the reaction mixture was quenched by addition of distilled water (5 ml) and this mixture was then stirred for an additional 1 min. The mixture was extracted with CH2Cl2(5×10 ml) and dried over anhydrous sodium sulfate.Evaporation of the solvent and short column chromatography of the resulting crude material over silicagel by eluent of Hexane/EtOAc: 9/1 affords the pure liquid benzyl alcohol (0.099 g, 92percent) as a sole product of reduction and acetophenone as an intact material (table 2, entry 1)
93% With sodium tetrahydroborate In methanol at 0 - 20℃; for 4 h; General procedure: To a solution of 3,4-dimethoxybenzaldehyde (1 g, 6 mmol) in methanol was added NaBH4 (0.27, 7.2 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 4 h, quenched with 3percent aqueous HCl solution, and evaporated to dryness. The residue was extracted with CH2Cl2 and the organic layer was dried with MgSO4. Evaporation of the dried organic layer yielded 0.96g (3,4-dimethoxyphenyl)methanol (6D0) as a white solid.
93% With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 30℃; for 12 h; Inert atmosphere To a solution of 3-methoxybenzaldehyde (3.11 g, 0.022 mole) in THF (10 mL) and methanol (20 mL), NaBH4 (1.43 g, 0.042 mole) was added portion wise at 0— 10 °C under nitrogen atmosphere. After addition, reaction mixture was stirred at RT for 12 hours. Reaction mixture was concentrated under vacuum and quenched in towater (50 mL). Aqueous layer was extracted with ethyl acetate (50 mL x 3). The organic layer was dried over Na2SO4 and concentrated under vacuum to get (3- methoxy-phenyl)-methanol.Yield: 2.95 g (93 percent); ‘H - NMR (CDC13, 400 MHz) ö ppm: 3.85 (s, 3H), 4.69 - 4.71 (m, 2H), 6.85 - 6.88 (m, 1H), 6.96 - 6.97 (m, 2H), 7.28 - 7.32 (m, 1H).
92% With sodium tetrahydroborate In methanol at 20℃; General procedure: Carbonyl substrate, 0.02 mol, was added in portions to a suspension of 0.01 mol NaBH4 in 0.3 mol of the corresponding alcohol solvent, and the mixture was stirred for 2–2.5 h at 20°C. The resulting boron derivatives of benzyl alcohols were decomposed with 10percent aqueous HCl (3.7 mL), and the mixture was stirred for a required time at a required temperature(see Tables 1–5), cooled, and poured into 200 mL of cold water. The products were extracted with diethylether (2 × 40 mL), the combined extracts were washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off on a rotary evaporator, and the residue was analyzed by 1H NMR. If necessary,benzyl ethers were isolated by chromatography. Alcohol coreactants poorly soluble in water were removed from the diethyl ether extracts by vacuum distillation, and the target ethers ware isolated from the still residue. Ethers 2a [9], 2c [3], 2h, 4a [10], 4b [11], 4i,4l, 7e, 10c, 10d, 10e [4], and 13a [12] were described previously. Ethers 2b, 2d–2g, 2i, 4c–4h, 4j, 4k, 4m–4w, 7a–7d, 7f, 7g, and 13b–13f are mobile liquids, and 7h–7j, 10a, 10b, and 10f–10i are viscous liquids.
83% With sodium dithionite; sodium hydrogencarbonate In water; isopropyl alcohol for 12 h; Inert atmosphere; Reflux General procedure: Benzaldehyde (1 g, 9.5 mmol, 1 equiv) was dissolved in 38 mL (1:1 IPA/ H2O), (0.25 M). Sodium dithionite (7.5 g, 43 mmol, 4.5 equiv) and NaHCO3 (1.6 g, 19 mmol, 2 equiv) was dissolved in water (43 mL, [1 M]) and added to the aldehyde. The mixture was refluxed for 12 hours under argon. The solution was allowed to cool to room temperature and the products were extracted using EtOAc (3 × 50 mL). This was dried using Na2SO4, filtered and dried under vacuum with a yield of 0.95 g (92percent). For entry 1.15 the compound was neutralized with 1 M HCl and extracted with EtOAc (3 × 50 mL) and washed with water (3 × 50 mL) the organic extracts were combined and dried using Na2SO4. The solvent was evaporated in vacuo and the resulting residue purified using column chromatography. Unless specified a 3:1 EtOAc/hexane eluent was used for chromatographic purification [1-3].
63% With sodium tetrahydroborate In ethanol; water for 4 h; Reflux General procedure: A mixture of an appropriate carbonyl compound (1 mmol),NaBH4 (1 mmol) and nanocatalyst (2 mg, 0.01 molpercent) was stirred for5 min, followed by addition of distilled water (3 mL). The reactionprogress was monitored by TLC or GC. After completion of thereaction the catalyst was separated by simplefiltration and theresidue was extracted with ethyl acetate and washed with water(5–7 times). The organic layer was dried over MgSO4,filtered off,evaporated to dryness under reduced pressure to give thecorresponding hydroxyl compounds.
31.5 %Chromat. With hydrogen In ethanol; water at 20℃; for 1 h; Autoclave General procedure: 0.05 g 5 wt.percent Pt catalyst was pretreated in a hydrogen flow at 673 K for 2 h before use. The catalyst was then mixed with 20 mL solvent and transferred to a 100 mL autoclave. The hydrogenation reaction began at a designated temperature after 4.0 MPa hydrogen was introduced into the autoclave. The reaction was stopped after an allotted period and the products were analyzed by GC–FID (GC-2014, Shimadzu Co.) equipped with a capillary column (DM-WAX, 30 m × 0.32 mm × 0.25 μm).

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YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 8 h; To a solution of 3-methoxybenzyl alcohol (20.0 g, 145 mmol) in THF (400 mL) was added N-bromosuccinimide (26 g, 146 mmol) and the resultant mixture was stirred at room temperature for 8 h. Ether (500 mL) was added and the mixture was washed with water (3×100 mL). The solution was dried over magnesium sulfate and concentrated to afford the title compound (31.2 g, 99percent) which was used as such for the next step.
88% With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 1.5 h; The compound 3-methoxybenzyl alcohol (10 g, 72.4 mmol) was dissolved in a mixture of acetonitrile (250 mL) and water (250 mL) and then sodium bromate (19.1 g, 127 mmol) and sodium bisulfite (13.2 g, 127 mmol) were added.
The reaction solution was stirred at room temperature for 1.5 hours, quenched with a saturated aqueous solution of sodium thiosulfate (250 mL) and then extracted with dichloromethane (200 mL*3).
The combined organic phase was washed with water (200 mL*3) and brine (20 mL) sequentially, dried over anhydrous sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure, the residue was purified by silica gel TLC preparative plate (petroleum ether: ethyl acetate=3:1) to give 9-e as a yellow solid (1.39 g, yield 88percent).
1H-NMR (400 MHz, MeOD) δ: 7.41 (d, J=12 Hz, 1H), 7.06 (d, J=4 Hz, 1H), 6.71 (dd, J=4 Hz, J=8 Hz, 1H), 4.70 (d, J=8 Hz, 2H), 3.81 (s, 3H) ppm
86% With sodium hydrogensulfite; potassium bromide In water; acetonitrile at 20℃; for 1.5 h; Method 10E: using the appropriate benzyl alcohol.Aromatic Bromination of the Benzyl AlcoholThe benzyl alcohol was dissolved in an equivolumetric acetonitrile/water mixture. Potassium bromide, then sodium hydrogenosulfite were added and the reaction mixture was stirred at room temperature for 1 h30. A sodium bisulfate 10percent solution was a added and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated sodium carbonate solution, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The product was chromatographed over silica gel.10.8.1
(4-bromo-3-methoxyphenyl)methanol
Prepared following the aromatic bromination method previously described (Method 10E) using (3-methoxyphenyl)methanol.
The product was chromatographed over silica gel (eluent petroleum ether/ethyl acetate 95/5).
The product was obtained as a beige solid.
Yield: 86percent
Rf (petroleum ether/ethyl acetate 90/10): 0.57
NMR 1H (CDCl3): 3.66 (s, 1H); 3.73 (s, 3H); 4.61 (s, 2H); 6.64 (dd, 1H, J=7.5 Hz, J=2.5 Hz); 7.01 (d, 1H, J=2.5 Hz); 7.34 (d, 1H, J=7.5 Hz).
Reference: [1] Patent: US9725406, 2017, B1, . Location in patent: Page/Page column 7-8
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[4] Patent: US2010/4159, 2010, A1, . Location in patent: Page/Page column 59; 64
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YieldReaction ConditionsOperation in experiment
81% With N-Bromosuccinimide In acetonitrile at 20℃; for 3 h; Example 1; 2-Bromo-5-Methoxybenzylalcohol [0044]; The title compound was prepared by reacting 3-methoxybenzyl alcohol (13. 82 g, 0.1 mol) and NBS (19. 58 g, 0.11 mol) in acetonitrile (250 mL) at room temperature for 3 hr. The solvent was removed and the resulting mass slurried in dichloromethane (250 mL) and filtered to remove the insoluble succinimide side product. The crude material was purified by chromatography (20percent EtOAc-hexanes) to provide a white solid (17.69 g, 81 percent), mp 57-58 °C.
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[3] Chemistry - A European Journal, 2011, vol. 17, # 39, p. 10906 - 10915
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YieldReaction ConditionsOperation in experiment
84% at 120℃; for 24 h; Inert atmosphere To a 20 mL tubular reactor was added 3-methoxybenzyl alcohol (69.0 mg, 0.50 mmol), triethyl phosphite(166.0 mg, 1.0 mmol, 2.0 equiv.) And tetrabutylammonium iodide (3.7 mg, 0.01 mmol, 2 molpercent), evacuated nitrogenAnd then heated to 120 ° C for 24 h under solvent-free conditions. After the TLC monitoring reaction was complete, the product was separated by column chromatographyPure, isolated yield 84percent.
Reference: [1] Patent: CN106543221, 2017, A, . Location in patent: Paragraph 0046; 0047; 0048; 0049
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[2] Journal of Organic Chemistry, 1982, vol. 47, # 18, p. 3447 - 3450
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