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[ CAS No. 2306-27-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2306-27-6
Chemical Structure| 2306-27-6
Structure of 2306-27-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2306-27-6 ]

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Product Details of [ 2306-27-6 ]

CAS No. :2306-27-6 MDL No. :MFCD00017421
Formula : C20H20O7 Boiling Point : -
Linear Structure Formula :- InChI Key :LKMNXYDUQXAUCZ-UHFFFAOYSA-N
M.W : 372.37 Pubchem ID :145659
Synonyms :
Pedalitin permethyl ether
Chemical Name :2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-chromen-4-one

Calculated chemistry of [ 2306-27-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.25
Num. rotatable bonds : 6
Num. H-bond acceptors : 7.0
Num. H-bond donors : 0.0
Molar Refractivity : 100.38
TPSA : 76.36 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.66
Log Po/w (XLOGP3) : 3.5
Log Po/w (WLOGP) : 3.5
Log Po/w (MLOGP) : 0.63
Log Po/w (SILICOS-IT) : 4.21
Consensus Log Po/w : 3.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.4
Solubility : 0.015 mg/ml ; 0.0000402 mol/l
Class : Moderately soluble
Log S (Ali) : -4.79
Solubility : 0.00609 mg/ml ; 0.0000163 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.71
Solubility : 0.0000724 mg/ml ; 0.000000195 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.68

Safety of [ 2306-27-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2306-27-6 ]

* 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.

  • Downstream synthetic route of [ 2306-27-6 ]

[ 2306-27-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2306-27-6 ]
  • [ 478-01-3 ]
  • 2
  • [ 1168-42-9 ]
  • [ 2306-27-6 ]
  • [ 481-53-8 ]
  • [ 1251-84-9 ]
  • [ 478-01-3 ]
  • [ 1178-24-1 ]
  • [ 2798-20-1 ]
  • [ 19103-54-9 ]
  • [ 21763-80-4 ]
  • [ 479-90-3 ]
  • [ 2174-59-6 ]
  • [ 1176-88-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ethanol; at 80℃; for 18 - 70h;Heating / reflux;Product distribution / selectivity; 54 g of the above obtained fraction were refluxed in 500 ml of a HCl solution in ethanol (1.25 M, Fluka) for 70 h. The ethanol was evaporated. About 100 ml of fresh ethanol <n="8"/>were added and evaporated to dryness. This was repeated two times. 46.5 g of 5-hydroxy polymethoxyflavones-rich fraction were obtained. This fraction contained at least 85% w/w of 5-desmethyl polymethoxyflavones, relative to total flavone fraction (HPLC- UV-MS). Further HPLC purification work and NMR analyses showed the presence of 5-desmethylsinensetin, 5-desmethyl<strong>[478-01-3]nobiletin</strong>, 5-desmethyltangeretin, 5-desmethyl-TOM- scutellarein, 5-desmethyl-HOM-quercetagenin and 5-hydroxy-3,6,7,8,34'- hexamethoxyflavone; 300 mg of a polymethoxyflavone-rich extract obtained in Example 3 were reacted at 8O0C in the presence of ethanolic HCl solutions having different amounts of water. All the different experiments were analysed by HPLC after 18 hours of reaction to monitor the progression. The results (UV-peak area) are shown in Table 1 hereinbelow:
With hydrogenchloride; ethanol; water; at 80℃; for 18h;Heating / reflux;Conversion of starting material; The same result was obtained in 1.6 ml of ethanol and 0.4 ml of concentrated HCl; 300 mg of a polymethoxyflavone-rich extract obtained in Example 3 were reacted at 8O0C in the presence of ethanolic HCl solutions having different amounts of water. All the different experiments were analysed by HPLC after 18 hours of reaction to monitor the progression. The results (UV-peak area) are shown in Table 1 hereinbelow: <n="9"/>PMF: polymethoxyflavoneAs it can be seen easily, if the water content of the alcoholic HCl solution is above 50% w/w, the yield of conversion is very low and preferably said water content should be below 33% or 20%.
With ethanol; water; for 24h;Heating / reflux;Product distribution / selectivity; 165 mg of the PMF rich fraction were refluxed over 24 hours in 1.8 ml of ethanol and 0.2 ml of concentrated aqueous. About 15 ml of water were added and the mixture was extracted two times with 5 ml of dichloromethane. The organic phase was dried over Na2SO4 and the solvent was evaporated. 124 mg (yield: 75%) of 5-hydroxy polymethoxyflavones-rich fraction were obtained. This fraction contained a proportion of 5-desmethyl polymethoxyflavones, relative to total flavones, higher than 95 % (HPLC- UV-MS).
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Technical Information

? Alkyl Halide Occurrence ? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Fischer Indole Synthesis ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Nomenclature of Ethers ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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