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[ CAS No. 14472-80-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 14472-80-1
Chemical Structure| 14472-80-1
Chemical Structure| 14472-80-1
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Quality Control of [ 14472-80-1 ]

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Product Details of [ 14472-80-1 ]

CAS No. :14472-80-1 MDL No. :MFCD11850091
Formula : C12H13ClO Boiling Point : -
Linear Structure Formula :- InChI Key :JNBOVWFOTNYTES-UHFFFAOYSA-N
M.W : 208.68 Pubchem ID :14617880
Synonyms :

Calculated chemistry of [ 14472-80-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.54
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 2.93
Log Po/w (WLOGP) : 3.57
Log Po/w (MLOGP) : 3.12
Log Po/w (SILICOS-IT) : 3.95
Consensus Log Po/w : 3.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.123 mg/ml ; 0.000588 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.234 mg/ml ; 0.00112 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.34
Solubility : 0.00943 mg/ml ; 0.0000452 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 14472-80-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14472-80-1 ]

* 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.

  • Upstream synthesis route of [ 14472-80-1 ]
  • Downstream synthetic route of [ 14472-80-1 ]

[ 14472-80-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 25253-51-4 ]
  • [ 14472-80-1 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 10, p. 1299 - 1312
[2] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 4910 - 4914
[3] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026,4
[4] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026
[5] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20208 - 20208
[6] Patent: WO2012/153162, 2012, A1, . Location in patent: Page/Page column 38
[7] Angewandte Chemie - International Edition, 2015, vol. 54, # 49, p. 14748 - 14752[8] Angew. Chem., 2015, vol. 127, # 49, p. 14961 - 14965,5
[9] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2454 - 2458[10] Angew. Chem., 2017, vol. 129, # 9, p. 2494 - 2498,5
  • 2
  • [ 1409956-58-6 ]
  • [ 14472-80-1 ]
  • [ 1409956-62-2 ]
  • [ 529-34-0 ]
YieldReaction ConditionsOperation in experiment
50% With toluene-4-sulfonic acid In toluene at 60℃; for 6 h; 2-(4-(4-chlorophenyl)-1-hydroxycyclohexyl)-3,4-dihydronaphthalen-1-(2H)-one (12.0 g, 0.0.034 mol) was charged in a reactor equipped with overhead stirrer, reflux condenser and thermo-pocket. Toluene (200 mL) was added to suspend the material and p-toluene sulfonic acid (0.3 g, 2.5 mol percent) was added to the reaction mass which was then heated to 60 °C and stirred for 6 h. Progress of reaction was monitored on TLC. After completion of reaction, reaction mass was cooled to RT and solvent was evaporated under pressure to obtain residue. To the residue, was added ethyl acetate (150 mL) and washed with sat. NaHC03 soln. and brine followed by evaporation of solvent to give crude product which was further recrystallised from methanol to afford white solid compound (5.3 g, 50 percent yield). The mother liquor obtained after re-crystallisation was subjected to GC analysis wherein both a-tetralone and 4-(4-chlorophenyl) cyclohexanone were identified to be present in approx. 1 : 1 ratio (by respective retention times and AUCs in the mother liquor) and in 50 percent yield. GC retention time: a-tetralone (XII): 17.21 min (Area percent : 46)
Reference: [1] Patent: WO2013/14486, 2013, A1, . Location in patent: Page/Page column 19
  • 3
  • [ 1409956-58-6 ]
  • [ 14472-80-1 ]
  • [ 529-34-0 ]
Reference: [1] Patent: WO2013/14486, 2013, A1, . Location in patent: Page/Page column 20
  • 4
  • [ 155098-65-0 ]
  • [ 14472-80-1 ]
YieldReaction ConditionsOperation in experiment
32%
Stage #1: With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; bis(pinacol)diborane In tetrahydrofuran for 12 h; Inert atmosphere; Reflux; Green chemistry
Stage #2: With copper dichloride In methanol; water for 6 h; Reflux; Green chemistry
The crude product 2 (150 g, 0.46 mol) obtained in the previous step was dissolved in anhydrous THF (750 ml)Then joinBiphenyl boronic acid(394.4 g, 1.55 mol),PdCl2 (dppf) (7.5 g, 5percent),Et3N (156.5 g, 1.55 mol),The reaction system was replaced with nitrogen twice,The reaction was heated to reflux for 12 hours.TLC detection reaction is complete,Quenching the reaction with water,After filtering the reaction solution,The filtrate was extracted twice with dichloromethane,Each time 500mL,Combined organic phase,After drying with anhydrous sodium sulfate,Concentrated organic phase,To give 140 g of the intermediate. dissolving the intermediate into methanol (600 mL)Then, 200 mL of an aqueous solution of copper chloride (104.5 g, 0.78 mol) was added,Reflux reaction for 6 hours,TLC detection reaction is complete,Cooled to room temperature,Dichloromethane (500 ml * 2) was extracted twice,Combined organic phase,Add 600ml saturated salt washed,Dried over anhydrous sodium sulfate,Concentrated organic phase,To give the product 4- (4-chlorophenyl) cyclohexanone as compound 3 (32.3 g, 0.15 mol)The yield is about 32percent.
Reference: [1] Patent: CN106496008, 2017, A, . Location in patent: Paragraph 0025; 0026; 0027; 0028
  • 5
  • [ 126991-60-4 ]
  • [ 14472-80-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 4910 - 4914
[2] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026,4
[3] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026
[4] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20208 - 20208
[5] Patent: WO2012/153162, 2012, A1,
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 10, p. 1299 - 1312
[7] Angewandte Chemie - International Edition, 2015, vol. 54, # 49, p. 14748 - 14752[8] Angew. Chem., 2015, vol. 127, # 49, p. 14961 - 14965,5
[9] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2454 - 2458[10] Angew. Chem., 2017, vol. 129, # 9, p. 2494 - 2498,5
  • 6
  • [ 126991-59-1 ]
  • [ 14472-80-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 4910 - 4914
[2] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
[3] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026,4
[4] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026
[5] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20208 - 20208
[6] Patent: WO2012/153162, 2012, A1,
[7] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 10, p. 1299 - 1312
[8] Angewandte Chemie - International Edition, 2015, vol. 54, # 49, p. 14748 - 14752[9] Angew. Chem., 2015, vol. 127, # 49, p. 14961 - 14965,5
[10] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2454 - 2458[11] Angew. Chem., 2017, vol. 129, # 9, p. 2494 - 2498,5
  • 7
  • [ 4746-97-8 ]
  • [ 14472-80-1 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
[2] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
[3] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2228 - 2231
[4] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026,4
[5] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026
[6] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20208 - 20208
[7] Patent: WO2012/153162, 2012, A1,
[8] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 10, p. 1299 - 1312
[9] Angewandte Chemie - International Edition, 2015, vol. 54, # 49, p. 14748 - 14752[10] Angew. Chem., 2015, vol. 127, # 49, p. 14961 - 14965,5
[11] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2454 - 2458[12] Angew. Chem., 2017, vol. 129, # 9, p. 2494 - 2498,5
  • 8
  • [ 106-39-8 ]
  • [ 14472-80-1 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026,4
[2] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 17023 - 17026
[3] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20208 - 20208
[4] Patent: WO2012/153162, 2012, A1,
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 10, p. 1299 - 1312
[6] Angewandte Chemie - International Edition, 2015, vol. 54, # 49, p. 14748 - 14752[7] Angew. Chem., 2015, vol. 127, # 49, p. 14961 - 14965,5
  • 9
  • [ 36716-71-9 ]
  • [ 14472-80-1 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
[2] Journal of Medicinal Chemistry, 1972, vol. 15, # 12, p. 1239 - 1243
  • 10
  • [ 36716-75-3 ]
  • [ 14472-80-1 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2228 - 2231
  • 11
  • [ 126991-59-1 ]
  • [ 25253-51-4 ]
  • [ 14472-80-1 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
  • 12
  • [ 637-87-6 ]
  • [ 14472-80-1 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
[2] Tetrahedron Letters, 1998, vol. 39, # 42, p. 7629 - 7632
  • 13
  • [ 101598-25-8 ]
  • [ 14472-80-1 ]
Reference: [1] Journal of Organic Chemistry, 1962, vol. 27, p. 4603 - 4606
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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 • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • 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 an Alkynyl Anion • Alkylation of Enolate Ions • An Alkane are Prepared from an Haloalkane • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chloroalkane Synthesis with SOCI2 • 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 • Convert Haloalkanes into Alcohols by SN2 • 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 • Deprotonation of Methylbenzene • Diorganocuprates Convert Acyl Chlorides into Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • 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 • 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 • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • 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 • Hiyama Cross-Coupling Reaction • 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 • 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 • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • 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 • Methylation of Ammonia • Michael Addition • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • 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 Alkylbenzene • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Strecker Synthesis • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • 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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