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[ CAS No. 480-66-0 ] {[proInfo.proName]}

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Chemical Structure| 480-66-0
Chemical Structure| 480-66-0
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Product Citations

Product Citations

Raaginie Tamil Segaran ; Chean Hui Ng ; Mohd Fadhlizil Fasihi Mohd Aluwi , et al. DOI:

Abstract: The synthesis of prenylated or geranylated acylphloroglucinol-based xanthenones with 15.1-36.9% yield was achieved via aldol condensation of 2,4,6-trihydroxy-3-prenylacetophenone (tHPA) or 2,4,6-trihydroxy-3-geranylacetophenone (tHGA) and 2-hydroxybenzaldehyde derivatives in the presence of lithium bis(trimethylsilyl)amide (LiHMDS) as deprotonating agent. This study is one of the first to report on the synthesis of xanthenones using strong non-nucleophilic base catalyst, and the described synthesis not only achieved a compound with a natural product skeleton but also formed in a simple and environmentally friendly specificity.

Keywords: Acylphloroglucinol-based xanthenone ; LiHMDS base catalyst ; Aldol condensation ; Natural product skeleton ; Eco-friendly

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Product Details of [ 480-66-0 ]

CAS No. :480-66-0 MDL No. :MFCD00002287
Formula : C8H8O4 Boiling Point : -
Linear Structure Formula :(HO)3C6H2COCH3 InChI Key :XLEYFDVVXLMULC-UHFFFAOYSA-N
M.W : 168.15 Pubchem ID :68073
Synonyms :
Chemical Name :2',4',6'-Trihydroxyacetophenone

Calculated chemistry of [ 480-66-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 42.71
TPSA : 77.76 ?2

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 : Yes
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.74
Log Po/w (XLOGP3) : 1.09
Log Po/w (WLOGP) : 1.01
Log Po/w (MLOGP) : -0.07
Log Po/w (SILICOS-IT) : 0.72
Consensus Log Po/w : 0.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.87
Solubility : 2.25 mg/ml ; 0.0134 mol/l
Class : Very soluble
Log S (Ali) : -2.32
Solubility : 0.814 mg/ml ; 0.00484 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.0
Solubility : 16.7 mg/ml ; 0.0995 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.1

Safety of [ 480-66-0 ]

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 [ 480-66-0 ]

* 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 [ 480-66-0 ]

[ 480-66-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 480-66-0 ]
  • [ 16600-92-3 ]
  • 2
  • [ 480-66-0 ]
  • [ 1570-05-4 ]
  • [ 951321-36-1 ]
  • 3
  • [ 480-66-0 ]
  • [ 1570-05-4 ]
  • [ 951321-36-1 ]
  • 2',4'-di(3,4-dibenzyloxybenzoyloxy)-6'-hydroxyacetophenone [ No CAS ]
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Technical Information

? Acidity of Phenols ? Appel Reaction ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Halogenation of Phenols ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Ritter Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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