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[ CAS No. 523-50-2 ] {[proInfo.proName]}

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Chemical Structure| 523-50-2
Chemical Structure| 523-50-2
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Product Details of [ 523-50-2 ]

CAS No. :523-50-2 MDL No. :MFCD00064930
Formula : C11H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XDROKJSWHURZGO-UHFFFAOYSA-N
M.W : 186.16 Pubchem ID :10658
Synonyms :
Isopsoralen;Bakuchicin;NSC 404563
Chemical Name :2H-Furo[2,3-h]chromen-2-one

Calculated chemistry of [ 523-50-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 13
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.26
TPSA : 43.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 2.54
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 2.91
Consensus Log Po/w : 2.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.19 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.447 mg/ml ; 0.0024 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.5
Solubility : 0.00587 mg/ml ; 0.0000316 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.07

Safety of [ 523-50-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 523-50-2 ]

* 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 [ 523-50-2 ]

[ 523-50-2 ] Synthesis Path-Downstream   1~69

  • 2
  • [ 59292-71-6 ]
  • [ 127-09-3 ]
  • [ 108-24-7 ]
  • [ 523-50-2 ]
  • 3
  • [ 59292-71-6 ]
  • [ 523-50-2 ]
  • 4
  • [ 523-50-2 ]
  • [ 623-11-0 ]
  • [ 77-78-1 ]
  • [ 1449-53-2 ]
  • 5
  • [ 523-50-2 ]
  • [ 77-78-1 ]
  • [ 1449-53-2 ]
  • 6
  • [ 523-50-2 ]
  • 3<i>t</i>-(4-hydroxy-benzofuran-5-yl)-acrylic acid [ No CAS ]
  • 7
  • [ 523-50-2 ]
  • [ 1001206-83-2 ]
  • 9
  • [ 523-50-2 ]
  • 5A,5b,12b,12c-tetrahydro-difuro[2,3-<i>h</i>;2',3'-<i>h'</i>]cyclobuta[1,2-<i>c</i>;4,3-<i>c'</i>] dichromium ene-5,6-dione [ No CAS ]
  • 10
  • [ 523-50-2 ]
  • 5A,5b,12a,12b-tetrahydro-difuro[2,3-<i>h</i>;2',3'-<i>h'</i>]cyclobuta[1,2-<i>c</i>;3,4-<i>c'</i>] dichromium ene-5,12-dione [ No CAS ]
  • 13
  • [ 116103-94-7 ]
  • [ 523-50-2 ]
  • [ 94522-81-3 ]
  • 14
  • [ 67-56-1 ]
  • [ 523-50-2 ]
  • [ 145039-58-3 ]
  • 15
  • [ 523-50-2 ]
  • [ 6544-86-1 ]
  • [ 51559-40-1 ]
  • [ 145039-59-4 ]
  • 16
  • [ 523-50-2 ]
  • [ 145039-59-4 ]
  • 17
  • [ 523-50-2 ]
  • [ 80673-10-5 ]
  • 18
  • [ 523-50-2 ]
  • Furo[2,3-h]chromene-2-thione [ No CAS ]
  • 20
  • [ 59292-71-6 ]
  • [ 1099-45-2 ]
  • [ 523-50-2 ]
  • 21
  • [ 184352-13-4 ]
  • [ 523-50-2 ]
  • 22
  • [ 197314-94-6 ]
  • [ 523-50-2 ]
  • 9-Allyl-2H,8H-benzo[1,2-b;3,4-b']dipyran-2,8-dione [ No CAS ]
  • 25
  • [ 119658-44-5 ]
  • [ 86119-84-8 ]
  • [ 523-50-2 ]
  • 26
  • [ 56-23-5 ]
  • [ 93-35-6 ]
  • [ 2032-35-1 ]
  • 7-hydroxy-coumarin sodium [ No CAS ]
  • [ 31005-02-4 ]
  • [ 523-50-2 ]
  • 27
  • [ 7446-70-0 ]
  • [ 523-50-2 ]
  • [ 71-43-2 ]
  • [ 31231-46-6 ]
  • 28
  • [ 444109-48-2 ]
  • [ 523-50-2 ]
  • 29
  • [ 16851-02-8 ]
  • [ 66-97-7 ]
  • [ 523-50-2 ]
  • 30
  • 8-(1-propenyl)-7-(vinyloxy)coumarin [ No CAS ]
  • [ 523-50-2 ]
  • 31
  • trans-8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one [ No CAS ]
  • [ 523-50-2 ]
  • 32
  • [ 26992-52-9 ]
  • [ 523-50-2 ]
  • 34
  • [ 849796-54-9 ]
  • [ 523-50-2 ]
  • 35
  • [ 93-35-6 ]
  • crotyl halide [ No CAS ]
  • [ 523-50-2 ]
  • 36
  • [ 31005-03-5 ]
  • [ 523-50-2 ]
  • 42
  • [ 184352-08-7 ]
  • [ 523-50-2 ]
  • 46
  • [ 523-50-2 ]
  • 5,6-furanohydrocoumaric acid methyl ester [ No CAS ]
  • 50
  • 3-Benzenesulfinyl-3,4-dihydro-2H-furo[2,3-h]chromene [ No CAS ]
  • [ 523-50-2 ]
  • 51
  • [ 35722-50-0 ]
  • [ 523-50-2 ]
  • 52
  • [ 6748-68-1 ]
  • [ 523-50-2 ]
  • 53
  • [ 129110-46-9 ]
  • [ 523-50-2 ]
  • 54
  • [ 523-50-2 ]
  • [ 6544-86-1 ]
  • 55
  • [ 523-50-2 ]
  • 3-(4-methoxy-benzofuran-5-yl)-propionic acid [ No CAS ]
  • 56
  • [ 523-50-2 ]
  • [ 1449-53-2 ]
  • 57
  • [ 116103-94-7 ]
  • [ 523-50-2 ]
  • 59
  • [ 480-97-7 ]
  • [ 523-50-2 ]
  • 60
  • [ 1361944-38-8 ]
  • [ 523-50-2 ]
  • 61
  • [ 523-50-2 ]
  • [ 2067-86-9 ]
  • C12H6O7 [ No CAS ]
  • 62
  • [ 523-50-2 ]
  • [ 2067-86-9 ]
  • C10H6O4 [ No CAS ]
  • 63
  • 8-(prop-1-en-1-yl)-7-(prop-1-en-1-yloxy)-2H-chromen-2-one [ No CAS ]
  • [ 523-50-2 ]
YieldReaction ConditionsOperation in experiment
95% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 90℃; for 1.0h;Inert atmosphere; General procedure: The appropriate precursors 9 or 10 (1.00 mmol) were dissolved in toluene (10 mL) andprecatalyst A (42 mg, 0.05 mmol, 5 mol %) was added. The mixture was heated to 90 C untilS10TLC indicated complete conversion (ca. 1 h), cooled to ambient temperature and evaporatedin vacuo. The residue was purified by column chromatography on silica using hexanes-MTBEmixtures of increasing polarity as eluents to furnish the products 3 or 11, respectively.
  • 64
  • [ 219489-13-1 ]
  • [ 2361306-76-3 ]
  • [ 523-50-2 ]
YieldReaction ConditionsOperation in experiment
47% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique; Sealed tube;
  • 65
  • [ 523-50-2 ]
  • [ 353-83-3 ]
  • [ 2595088-94-9 ]
YieldReaction ConditionsOperation in experiment
34% With tris[2-phenylpyridinato-C2,N]iridium(III); potassium carbonate In dimethyl sulfoxide at 20℃; for 12h; Schlenk technique; Irradiation; Inert atmosphere;
  • 66
  • [ 523-50-2 ]
  • [ 371-67-5 ]
  • [ 2687981-26-4 ]
YieldReaction ConditionsOperation in experiment
36% With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane; tert-butyl methyl ether at 80℃; for 96h;
  • 67
  • [ 523-50-2 ]
  • [ 2091753-13-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
54% With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium acetate In dimethyl sulfoxide at 45℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;
  • 68
  • [ 523-50-2 ]
  • [ 35024-12-5 ]
  • [ 66645-40-7 ]
YieldReaction ConditionsOperation in experiment
55% With Bromoeosine; potassium carbonate In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique;
55% With potassium carbonate; Eosin In dimethyl sulfoxide at 25℃; for 12h; Irradiation; 22 Synthesis of Compound (I-22) Isopsoralen 0.1mmol, iodine ylide 0.15mmol,Eosin Y 0.002mmol, potassium carbonate 0.1mmol were added to the reaction tube,Soluble in dimethyl sulfoxide solvent, 25,The reaction was carried out under LED illumination for 12 hours, and the target product (I-22) was obtained by column chromatography, and the isolated yield was 55%.
  • 69
  • [ 523-50-2 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
89% With 2,4,6-triisopropylbenzenethiol In tetrahydrofuran at 20℃; for 24h; Irradiation; Inert atmosphere; Schlenk technique; regioselective reaction;
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Alkylation of Enolate Ions • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Conjugated Enone Takes Part in 1,4-Additions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Diorganocuprates Convert Acyl Chlorides into Ketones • Dithioacetal Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reaction • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Michael Addition • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reductive Amination • Reductive Amination • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Strecker Synthesis • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Wittig Reaction • Wolff-Kishner Reduction
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