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[ CAS No. 577-56-0 ] {[proInfo.proName]}

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Chemical Structure| 577-56-0
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Product Details of [ 577-56-0 ]

CAS No. :577-56-0 MDL No. :MFCD00002475
Formula : C9H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :QDAWXRKTSATEOP-UHFFFAOYSA-N
M.W : 164.16 Pubchem ID :68474
Synonyms :

Calculated chemistry of [ 577-56-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.6
TPSA : 54.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : 0.81
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 1.28
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.61
Solubility : 4.07 mg/ml ; 0.0248 mol/l
Class : Very soluble
Log S (Ali) : -1.53
Solubility : 4.81 mg/ml ; 0.0293 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.1
Solubility : 1.31 mg/ml ; 0.00798 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 577-56-0 ]

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 [ 577-56-0 ]

* 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.

  • Upstream synthesis route of [ 577-56-0 ]
  • Downstream synthetic route of [ 577-56-0 ]

[ 577-56-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 577-56-0 ]
  • [ 5693-27-6 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With hydrogen bromide; bromine; acetic acid In chlorobenzene at 30℃; for 3 h;
Stage #2: With water In chlorobenzene for 3 h; Reflux
Example 2: Preparation of 1 /-/-2-benzopyran-1 ,4(3/-/)-dione (Compound of formula (III))A stirred mixture of 2-acetylbenzoic acid (compound of formula (XI)) (1.00 Kg, 6.09 mol) and chlorobenzene (10.0 L) was treated with 5.5 molar hydrobromic acid in acetic acid (55 ml_) and bromine (310 ml_) then warmed to approximately 30 °C. After 3 hours water (10.0 L) was added and the reaction heated to reflux. After 3 hours the reaction was cooled to 60 °C and the organic layer removed. The aqueous layer was extracted with chlorobenzene (2.0 L) and the combined organic layers concentrated under reduced pressure to approximately 3.0 L. Propan-2-ol (5.0 L) was charged and the slurry cooled to 0 °C before being filtered and washed with propan-2-ol (2.0 L). The resulting solid was dried in vacuo at 50 °C to give the title compound (736 g, 75percent); 1 H NMR (400MHz, CDCI3): δ 5.14 (2H, s, H-9), 7.82 - 7.91 (2H, m, H-2 and 3), 8.08 - 8.10 (1 H, m, H-1), 8.28 - 8.30 (1 H, m, H-4); 13C NMR (100MHz, CDCIs) δ 73.4, 125.6, 128.0, 130.9, 131.8, 134.7, 135.9, 161.4 and 189.5.
63% at 40℃; for 0.5 h; Step 1: lH-Isochromene-l,4(3H)-dione [00369] To a solution of 2-acetylbenzoic acid (8.458 g, 51.52 mmol) in acetic acid (50.0 mL, 879 mmol) was added 30 ml of 33percent HBr in acetic acid. Bromine (8.646 g, 54.10 mmol) was next added to the solution, and the reaction was heated to 40 °C with stirring for 30 min. The reaction mixture was poured into 300 ml water, the layers were separated, and the aqueous layer was extracted with 3 x 100ml DCM. Combined the organic layers and concentrated in vacuo to yield crude intermediate, which was dissolved in 25 ml acetic acid, 130ml toluene and 30 ml water. The resulting mixture was stirred at reflux overnight. The reaction was cooled to rt, and the layers were separated. The organic layer was concentrated in vacuo and purified by flash column ( 120g column, eluent 0-55percent EtOAc in hexane)to afford 5.24g (63percent) of title compound. NMR (400 MHz, Chloroform-d) δ 8.36 - 8.28 (m, 1 H), 8.17 - 8.07 (m, 1 H), 7.95 - 7.79 (m, 2H), 5.16 (s, 2H).
Reference: [1] Patent: WO2012/80243, 2012, A2, . Location in patent: Page/Page column 15-16
[2] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 8,
[3] Patent: WO2016/4136, 2016, A1, . Location in patent: Paragraph 00369
[4] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1607 - 1617
  • 2
  • [ 577-56-0 ]
  • [ 5693-27-6 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1607 - 1617
  • 3
  • [ 577-56-0 ]
  • [ 7726-95-6 ]
  • [ 5693-27-6 ]
Reference: [1] Journal of the Chemical Society, 1963, p. 402 - 410
  • 4
  • [ 577-56-0 ]
  • [ 3453-64-3 ]
  • [ 57259-71-9 ]
  • [ 767-90-8 ]
Reference: [1] Chemistry Letters, 1993, # 9, p. 1495 - 1498
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • 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 • Alkyl Halide Occurrence • Alkylation of Aldehydes or Ketones • Alkylation of Enolate Ions • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • An Alkane are Prepared from an Haloalkane • Anhydride Hydrolysis • Arndt-Eistert Homologation • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Basicity of Amines • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Chan-Lam Coupling Reaction • Chichibabin Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • 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 • Deprotection of Cbz-Amino Acids • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Diorganocuprates Convert Acyl Chlorides into Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Esters Hydrolyze to Carboxylic Acids and Alcohols • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • 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 • Hofmann Elimination • Hofmann Rearrangement • Horner-Wadsworth-Emmons Reaction • Hunsdiecker-Borodin 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 • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • 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 • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Methylation of Ammonia • Methylation of Ammonia • Michael Addition • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nitrosation of Amines • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Paternò-Büchi Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Preparation of LDA • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Nitro Group Conver to the Amino Function • 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 • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction
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