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[ CAS No. 6754-58-1 ] {[proInfo.proName]}

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Chemical Structure| 6754-58-1
Chemical Structure| 6754-58-1
Structure of 6754-58-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6754-58-1 ]

CAS No. :6754-58-1 MDL No. :MFCD00210576
Formula : C21H22O5 Boiling Point : -
Linear Structure Formula :- InChI Key :ORXQGKIUCDPEAJ-YRNVUSSQSA-N
M.W : 354.40 Pubchem ID :639665
Synonyms :

Calculated chemistry of [ 6754-58-1 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.19
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 102.53
TPSA : 86.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.93
Log Po/w (XLOGP3) : 5.07
Log Po/w (WLOGP) : 4.11
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 4.31
Consensus Log Po/w : 3.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.18
Solubility : 0.00236 mg/ml ; 0.00000665 mol/l
Class : Moderately soluble
Log S (Ali) : -6.64
Solubility : 0.0000814 mg/ml ; 0.00000023 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.58
Solubility : 0.00926 mg/ml ; 0.0000261 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.16

Safety of [ 6754-58-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6754-58-1 ]

* 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.

  • Downstream synthetic route of [ 6754-58-1 ]

[ 6754-58-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6754-58-1 ]
  • [ 189299-05-6 ]
YieldReaction ConditionsOperation in experiment
74% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 95℃; for 4h; 3.3.2. Xanthohumol C (2) DDQ (227 mg, 1 mmol) and 1 (354 mg, 1 mmol) were dissolved in anhydrous 1,4-dioxane (25 mL).The reaction mixture was heated to 95 °C for 4 h, then cooled to room temperature and 40 mL of ethylacetate was added. The mixture was washed with equal volumes (20 mL) of water, saturated NaHCO3solution, water and brine. The organic phase was dried over MgSO4, evaporated and purified bycolumn chromatography (eluent: chloroform-methanol 9:1) to give xanthohumol C (2): yield 74%,orange amorphous powder; UV (MeOH) λmax 233, 285, 370 nm; 1H-NMR (600 MHz, acetone-d6) δ:1.42 (6H, s, H-4'', H-5''), 3.97 (3H, s, C6'-OCH3), 5.53 (1H, d, J = 9.9 Hz, H-2''), 6.00 (1H, s, H-5'),6.62 (1H, d, J = 9.9 Hz, H-1''), 6.92 (2H, m, J = 7,1 Hz, H-3, H-5), 7.59 (2H, m, J = 7.1 Hz, H-2, H-6), 7.76 (1H, d, J = 15.4 Hz, H-β), 7.85 (1H, d, J = 15.4 Hz, H-α), and 14.85 (s, C2'-OH); 13C-NMR (150 MHz,acetone-d6) δ: 28.52 (C-4'', C-5''), 56.46 (C6'-OCH3), 78.73 (C-3''), 92.34 (C-5'), 103.36 (C-3'), 106.46(C-1'), 116.53 (C-1''), 116.76 (C-3, C-5), 124.96 (H-α), 126.20 (C-2''), 127.87 (C-1), 131.30 (C-2, C-6),143.71 (H-β), 160.66 (C-4), 161.01 (C-4'), 163.24 (C-2'), 163.64 (C-6'), and 193.32 (C=O). HR ESI-MS m/z:351.1234 [M - H]- (calcd for C21H20O5 - H, 351.1238).
55.4% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; benzene at 120℃; for 0.05h; Microwave irradiation; 2 Synthesis of (E)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one (compound 1a; ENDF 1) A solution of xanthohumol (200 mg, 0.56 mmol, 1 eq) and 2,3-Dichloro-5,6-dicyanobenzoquinone (Jain. Gupta, et al. Tetrahedron 1978, 34(24), 3563-3567) (128 mg, 0.56 mmol, 1 eq) in 1 ml benzene (dry) with 2 drops of dioxan was radiated in microwave at 120° C. for 3 min. Dicyanobenzoquinone (DDQ) was separated by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexane: 2/3) to give 109.2 mg (55.4%) of a yellow solid, M=352 g/mol (C21H20O5). 1H-NMR (CDCl3): δ (ppm): 1.44 (s, 6H, 2*CH3), 3.89 (s, 3H2OCH3), 5.44 (d, J=11.03 Hz, 1H, H-5'), 5.9 (s, 1H, H-5"), 6.63 (d, J=11.03 Hz, 1H, H-4"), 6.84 (d, J=8.58 Hz, 2H, H-3 & H-5), 7.46 (d, J=8.58 Hz, 2H, H-2 & H-6), 7.7 (s, 2H, H-β & H-α), 14.60 (s, 1H, -OH) 13C-NMR (CDCl3): 192.8 (CO), 162.6 (C-2'), 162.5 (C-4'), 160.3 (C-6'), 157.7 (C-4), 142.4 (C-(3), 130.3 (C-2 & C-6), 128.5 (C-1), 125.4 (C-5"), 125.3 (C-α), 116.1 (C-3 & C-5), 106.2 (C-1'), 103.1 (C-3'), 91.6 (C-5'), 78.3 (C-6"), 55.9 (OCH3), 28.4 (C-7"& C-8")
51% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 120℃; for 0.0833333h; Synthesis of Xanthohumol C (2E)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one 350 mg (1 mmol) of Xanthohumol and 227 mg (1 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone were dissolved in1 mL of dry benzene. The reaction mixture was heated in a mono mode microwave (CEM Discover S-class) at 120°C for 5min. The product was extracted with ethyl acetate and purified using automated column chromatography (Interchim, Puriflash 4250) (51% yield) [5]. 1H-NMR (CDCl3): δ (ppm) = 1.44 (s, 6H, 7″-H & 8″-H),3.89 (s, 3H, OCH3), 5.44 (d, 1H, J = 11.03 Hz, 5″-H), 5.90 (s, 1H,5′-H), 6.63 (d, 1H, J = 11.03Hz, 4″-H), 6.84 (d, 2H, J = 8.58Hz, 3-H & 5-H), 7.46 (d, 2H, J = 8.58 Hz, 2-H & 6-H), 7.70 (s, 2H, H-α&H-β), 14.60 (s, 1H, OH).
50% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; benzene at 120℃; for 0.05h; Microwave irradiation;
1.9 mg With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 2.5h; Heating;
80 % With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 120℃;

  • 2
  • [ 6754-58-1 ]
  • [ 250603-94-2 ]
YieldReaction ConditionsOperation in experiment
87% With aluminum (III) chloride In dichloromethane at 20℃; for 5h; 3.3.3. 1'',2''-Dihydroxanthohumol C (3) A mixture of 1 (354 mg, 1 mmol), anhydrous AlCl3 (532 mg, 4 mmol) and methylene chloride(100 mL) was stirred at room temperature for 5 h. The reaction mixture was filtered, the filtrate washedwith water (3 70 mL), dried overMgSO4, evaporated and purified by column chromatography (eluent:chloroform-methanol 9:1) to yield 1'',2''-dihydroxanthohumol C (3): yield 87%, orange amorphouspowder; UV (MeOH) max 370 nm; 1H-NMR (600MHz, acetone-d6) : 1.34 (6H, s, H-4'', H-5''), 1.81 (2H,t, J = 6.8 Hz, H-2''), 2.57 (2H, t, J = 6.8 Hz, H-1''), 3.95 (3H, s, C6'-OCH3), 5,93 (1H, s, H-5'), 6.92 (2H,m, J = 8.6 Hz, H-3, H-5), 7.60 (2H, m, J = 8.6 Hz, H-2, H-6), 7.76 (1H, d, J = 15.5 Hz, H-α), 7.91 (1H, d,J = 15.5 Hz, H-β) and 14.93 (s, C2'-OH); 13C-NMR (600 MHz, acetone-d6) δ: 16.77 (C-1''), 26.90 (C-4'',C-5''), 32.60 (C-2''), 56.22 (C6'-OCH3), 76.68 (C-3''), 92.59 (C-5'), 102.47 (C-3'), 105.97 (C-1'), 116.79 (C-3,C-5), 125.26 (C-α), 128.07 (C-1), 131.25 (C-2, C-6), 143.31 (C-β), 160.60 (C-4'), 161.72 (C-2'), 161.75 (C-6'),166.41 (C-4), 193.16 (C=O); HR ESI-MS m/z: 353.1391 [M - H]- (calcd for C21H22O5 - H, 353.1394).
77% With polyphosphoric acid; air In N,N-dimethyl-formamide at 110℃; for 2h; regioselective reaction; 2. General Procedure for the Synthesis of carbonyl-containing dihydrobenzofurans/dihydrobenzopyrans 2 (2a-2k) General procedure: To a stirred solution of N,N-dimethylformamide (DMF, 0.3 mL) were added PPA (1 mmol) and carbonyl-containing ortho-allyl/prenylphenols 1 (0.2 mmol) in 5 mL pressure-resistant reaction bottle. The reaction mixture was stirred at 90-160 °C until all starting materials were consumed (2-10 h). The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, dried over Na2SO4 and evaporated. The resulting crude compound was purified by silica gel column chromatography, affording the pure dihydrobenzofurans/dihydrobenzopyrans 2.
37.5% In formic acid at 50℃; for 0.0833333h; Microwave irradiation; Cooling; 4 Synthesis of (E)-1-(5-hydroxy-7-methoxy-2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one (compound 1b; ENDF 3) A solution of xanthohumol (200 mg, 0.56 mmol) in formic acid (2 ml) was radiated in a 10 ml microwave vial with snap-on-cap at 50° C. with pressurized air cooling for 5 min. The resulting mixture was given to ice-water. The precipitate was filtrated, washed with cold water and was purified by silica gel chromatography (ethyl acetate/hexane: 1/3) to give 75 mg (37.5%) yellow solid, M=354 g/mol (C21H22O5). 1H-NMR (CDCl3): δ (ppm): 1.35 (s, 6H, 2×CH3), 1.79 (t, J=7.32 Hz, 2H, H-5″), 2.62 (t, J=6.12 Hz, 2H, H-4″), 3.86 (s, 3H2OCH3), 5.88 (s, 1H, H-5′), 6.86 (d, J=8.56 Hz, 2H, H-3 & H-5), 7.47 (d, J=7.36 Hz, 2H, H-2 & H-6), 7.85 (dd, J=15.9 Hz, 2H, H-α & H-β) 14.80 (s, 1H, -OH) 13C-NMR (CDCl3): 192.39 (CO), 165.14 (C-2′), 160.53 (C-4′), 160.49 (C-4), 157.49 (C-6′), 141.91 (C-β), 129.93 (C-2 & C-6), 128.01 (C-1), 124.97 (C-α), 115.60 (C-3 & C-5), 105.26 (C-1′), 101.75 (C-5′), 91.62 (C-3′), 75.90 (C-6″), 55.35 (OCH3), 31.83 (C-5″) 26.38 (C-7″&C-8″), 15.76 (C-4″)
37% With formic acid at 50℃; for 0.0833333h; Microwave irradiation;
Multi-step reaction with 2 steps 1.1: NaOH / H2O / 2 h / 0 °C 2.1: CH3AlCl2 / CH2Cl2 / 1.5 h / 0 °C 2.2: 70 percent Chromat. / NaOH / H2O / 1.5 h / 0 °C
Multi-step reaction with 2 steps 1.1: NaOH / H2O / 2 h / 0 °C 2.1: sym-collidine; BBr3 / CH2Cl2 / 3 h / -80 °C 2.2: 4 percent / NaOH / H2O / 1.5 h / 0 °C

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