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Product Details of [ 1700-30-7 ]

CAS No. :1700-30-7 MDL No. :MFCD00004642
Formula : C14H14O2 Boiling Point : -
Linear Structure Formula :HOCH2C6H4OCH2C6H5 InChI Key :AFKLSWIRJUJWKY-UHFFFAOYSA-N
M.W : 214.26 Pubchem ID :74341
Synonyms :

Calculated chemistry of [ 1700-30-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.55
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 2.9
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 3.27
Consensus Log Po/w : 2.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.29
Solubility : 0.111 mg/ml ; 0.000517 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.142 mg/ml ; 0.000662 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.9
Solubility : 0.00272 mg/ml ; 0.0000127 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 1700-30-7 ]

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 [ 1700-30-7 ]

* 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 [ 1700-30-7 ]
  • Downstream synthetic route of [ 1700-30-7 ]

[ 1700-30-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1700-30-7 ]
  • [ 1700-37-4 ]
YieldReaction ConditionsOperation in experiment
83% With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1,10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).
Reference: [1] Archiv der Pharmazie, 2007, vol. 340, # 5, p. 244 - 250
[2] Tetrahedron, 2006, vol. 62, # 14, p. 3389 - 3394
[3] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087
[4] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 14, p. 1791 - 1793
  • 2
  • [ 1700-30-7 ]
  • [ 587-33-7 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 19, p. 6690 - 6691
  • 3
  • [ 1700-30-7 ]
  • [ 1700-31-8 ]
YieldReaction ConditionsOperation in experiment
97% With phosphorus tribromide In diethyl ether Synthesis of Compound 172
Preparation of (3-benzyloxy)benzyl bromide:
To a solution of (3-benzyloxy)benzyl alcohol (3.0 g, 14.0 mmol) in anhydrous diethyl ether (50 mL) was added PBr3 (0.66 mL, 7.0 mmol) in one portion, and the resulting mixture was stirred at room temperature for 3 hours.
The mixture was diluted with diethyl ether (60 mL) and washed with H2O (2*40 mL), saturated NaHCO3 (2*40 mL), and brine (2*40 mL).
The ether layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford (3-benzyloxy)benzyl bromide (3.76 g, 97percent) as a pale yellow solid.
97% With phosphorus tribromide In diethyl ether Synthesis of Compound 172
Preparation of (3-benzyloxy)benzyl bromide:
To a solution of (3-benzyloxy)benzyl alcohol (3.0 g, 14.0 mmol) in anhydrous diethyl ether (50 mL) was added PBr3 (0.66 mL, 7.0 mmol) in one portion, and the resulting mixture was stirred at room temperature for 3 hours.
The mixture was diluted with diethyl ether (60 mL) and washed with H2O (2*40 mL), saturated NaHCO3 (2*40 mL), and brine (2*40 mL).
The ether layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford (3-benzyloxy)benzyl bromide (3.76 g, 97percent) as a pale yellow solid.
89% With phosphorus tribromide In dichloromethane at 0 - 20℃; for 3 h; Using the procedure reported by K. Thakkar et al., J. Med. Chem., 1993, 36 (20), 2950. [0500] Phosphorus tribromide (1.96 mL, 20.6 mmol) was added to a solution of 3-benzyloxybenzyl alcohol (4.29 g, 20 mmol) in anhydrous dichloromethane (90 mL) at 0° C. The mixture was stirred at 0° C. for 2 h and then at room temperature for 1 h. The reaction was poured onto ice/water (400 mL) and allowed to warm to room temperature. The aqueous solution was extracted with Et2O (5.x.100 mL) and the combined ethereal solution dried (MgSO4). Concentration in vacuo gave a light yellow oil which crystallised on standing to give OBS01018 as colourless needles (4.93 g, 89percent). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.9; m.p. 55-56° C. [Lit. (Petroleum ether): 55° C.]; 1H-NMR (400 MHz, CDCl3) 4.44 (2H, s), 5.05 (2H, s); 6.78 (1H, d, J=2), 6.93 (1H, m), 7.22 (1H, t, J=8), 7.40 (5H, m).
64% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 2 h; 3-Hydroxybenzaldehyde (5.00 g, 0.041 mol) was dissolved in anhydrous acetonitrile (130 mL) under argon atmosphere. Cesium carbonate (20.01 g, 0.061 mol) was added and the suspension stirred for 5 min. Benzyl bromide (11.69 mL, 0.102 mol) was then added and the solution heated at reflux for 16 h. The solution was concentrated on rotary evaporator, water was added and the mixture was extracted with EtOAc. The organic phase was washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. Water was added and the mixture was extracted with CH2Cl2. The crude product was purified by flash chromatography on silica gel with hexanes/EtOAc (80/20) to yield 3a as a white solid (8.59 g). 1H NMR δ (CDCl3) 5.13 (s, 2H, PhCH2O), 5.33 (s, 2H, COOCH2Ph), 7.35-7.50 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O), 10.00 (s, 1H, PhCHO). The aldehyde 3a was dissolved in anhydrous THF (200 mL) under argon and cooled to 0 °C. Lithium aluminum hydride (1.55 g, 0.041 mol) was added in small portions and the solution stirred at room temperature for 2 h. The reaction was then quenched using water (0.8 mL), a 10percent wt aqueous NaOH solution (1.15 mL) and water again (1.9 mL) and left to settle. The suspension was then filtered and concentrated. Water was added and the mixture extracted with EtOAc, the organic phase dried over MgSO4, filtered and concentrated to yield 7.07 g crude alcohol 3b. 1H NMR δ (CDCl3) 4.68 (s, 2H, PhCH2OH), 5.08 (s, 2H, PhCH2O), 6.90-7.46 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O). Crude alcohol 3b (7.06 g) was dissolved in anhydrous CH2Cl2 (330 mL) and the solution cooled to 0 °C. Triphenylphosphine (17.28 g, 0.066 mol) and carbon tetrabromide (21.85 g, 0.066 mol) were then added and the solution stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phase was dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography on silica gel with hexanes/EtOAc (9/1) to yield 5.85 g (64percent) of bromide 3c. 1H NMR δ (CDCl3) 4.47 (s, 2H, PhCH2Br), 5.07 (s, 2H, PhCH2O), 6.90-7.46 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O); 13C NMR (75 MHz) δ (acetone-d6) 32.5, 69.4, 114.3, 114.8, 121.0, 127.0 (2.x.), 127.2, 127.8, 128.0, 129.3, 136.1, 138.6, 158.3.
56% With phosphorus tribromide In diethyl ether at 20℃; for 3 h; Cooling with ice In an ice cooled solution of 3-benzyloxy-phenylmethanol (2.14 g, 10 mmol) in Et2O (25 mL), PBr333 (1.41 mL, 15 mmol) was added dropwise. The mixture was stirred at room temperature for 3 h and the reaction mixture was quenched by the addition of H2O (15 mL) in small portions at 0 °C. The aqueous phase was removed and the organic layer was washed with H2O, dried over Na2SO4 and evaporated in vacuo. The product was purified by column chromatography (silica gel) using petroleum ether (bp 40-60 °C)-EtOAc, 7:3 as eluent. Yield 1.5 g (56percent); yellow oil.1H NMR (CDCl3) δ: 7.42-6.82(m, 9H, Ph), 5.06(s, 2H, OCH2Ph), 4.46(s, 2H, BrCH2Ph).13C NMR δ: 159.0, 139.2, 136.7, 129.8, 128.6, 128.0, 127.5, 121.5, 115.4, 114.9 70.0(OCH2Ph), 33.4(BrCH2Ph).Anal. Calcd for C14H13BrO: C, 60.67; H, 4.73. Found: C, 60.46; H, 4.69.

Reference: [1] Patent: US2003/186943, 2003, A1,
[2] Patent: US6458829, 2002, B1,
[3] Patent: US6770658, 2004, B2,
[4] Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6703 - 6714
[5] Journal of Organic Chemistry, 1997, vol. 62, # 19, p. 6690 - 6691
[6] Patent: US2004/19016, 2004, A1, . Location in patent: Page/Page column 43
[7] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2950 - 2955
[8] Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 1, p. 13 - 18
[9] Journal of Agricultural and Food Chemistry, 2000, vol. 48, # 6, p. 2547 - 2555
[10] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4227 - 4237
[11] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2888 - 2902
[12] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 86 - 95
[13] Journal of the Chemical Society, 1965, p. 3645 - 3660
[14] Tetrahedron, 1992, vol. 48, # 5, p. 819 - 830
[15] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
[16] Journal of Organic Chemistry, 1994, vol. 59, # 20, p. 5999 - 6007
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[18] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 18, p. 2447 - 2450
[19] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3540 - 3560
[20] Tetrahedron Letters, 2006, vol. 47, # 35, p. 6281 - 6284
[21] Patent: US6034118, 2000, A,
[22] Patent: US5705524, 1998, A,
[23] Patent: US5811450, 1998, A,
[24] Patent: WO2006/55434, 2006, A2, . Location in patent: Page/Page column 52
[25] RSC Advances, 2015, vol. 5, # 100, p. 82153 - 82158
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