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[ CAS No. 4500-20-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4500-20-3
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Chemical Structure| 4500-20-3
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Product Details of [ 4500-20-3 ]

CAS No. :4500-20-3 MDL No. :MFCD00456899
Formula : C12H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :JTLAHVRPWDIEMU-UHFFFAOYSA-N
M.W : 189.25 Pubchem ID :343882
Synonyms :

Calculated chemistry of [ 4500-20-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.74
TPSA : 32.59 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) : -5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 3.17
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.251 mg/ml ; 0.00133 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.243 mg/ml ; 0.00128 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.0962 mg/ml ; 0.000508 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.55

Safety of [ 4500-20-3 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P280-P210-P240-P264-P270-P301+P310-P330-P370+P378-P403+P233-P405-P501 UN#:1325
Hazard Statements:H228-H302-H317-H319-H341-H351 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4500-20-3 ]

* 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 [ 4500-20-3 ]

[ 4500-20-3 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 4500-20-3 ]
  • [ 7500-39-2 ]
YieldReaction ConditionsOperation in experiment
96% With polyphosphoric acid at 120℃; for 4h;
91% With trifluorormethanesulfonic acid; 4 A molecular sieve; hydroxylamine hydrochloride; tetrabutylammonium perrhenate In nitromethane for 1h; Heating;
91% With trifluorormethanesulfonic acid; hydroxylamine hydrochloride; tetrabutylammonium perrhenate In acetonitrile for 1h; Heating;
With thionyl chloride In 1,4-dioxane at 20℃; for 0.5h;
With thionyl chloride In 1,4-dioxane at 20℃; for 0.5h;

  • 2
  • [ 4500-20-3 ]
  • N-(4-Phenyl-cyclohexyl)-hydroxylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diborane In tetrahydrofuran for 4h; Ambient temperature;
  • 3
  • [ 4500-20-3 ]
  • [ 1079-66-9 ]
  • [ 172847-44-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane; Petroleum ether at -40℃;
With triethylamine In dichloromethane; Petroleum ether at -50℃; for 2h;
  • 4
  • [ 2270-20-4 ]
  • [ 4500-20-3 ]
  • (R,S)-4-phenylcyclohexanone oxime 5-phenylvalerate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide In dichloromethane
  • 5
  • [ 4894-75-1 ]
  • [ 4500-20-3 ]
YieldReaction ConditionsOperation in experiment
100% With hydroxylamine hydrochloride In ethanol at 50 - 60℃; for 0.25h;
97% With hydroxylamine hydrochloride; sodium acetate In ethanol; water 34.1 Preparation of (4-[1-((3S)-3-methylpiperazinyl)(1Z)-2-aza-2-(4-phenylcyclohexyl)vinyl]amino}phenyl)-N-[2-(2,4-dichlorophenyl)ethyl]carboxamide Step 1. Preparation of 1-(hydroxyimino)-4-phenylcyclohexane. A mixture of 4-phenylcyclohexanone (28.7 mmol), hydroxylamine hydrochloride (36.0 mmol), and sodium acetate (60.95 mmol) in ethanol and water was heated at 70° C. overnight. Ethanol was removed, and the residue was dissolved in water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated to give 1-(hydroxyimino)-4-phenylcyclohexane (97%).
86% With ammonium chloride In ethanol for 1h; Ambient temperature;
85% With hydroxylamine hydrochloride; silica gel; <i>tert</i>-butyl alcohol for 0.183333h;
74% With hydroxylamine hydrochloride; sodium acetate In methanol; water at 60℃;
With sodium hydroxide; hydroxylamine hydrochloride In ethanol Heating;
With pyridine; hydroxylamine hydrochloride In ethanol Heating;
With hydroxylamine hydrochloride; sodium acetate In ethanol at 80℃; for 1h;
106 g With hydroxylamine hydrochloride; potassium hydroxide In ethanol; water for 2h; Reflux; 1 Example 1.Preparation of 4-Phenylcyclohexanone oxime 1 4-phenylcyclohexanone (100 g, 0.57 mol)Hydroxylamine hydrochloride (100 g, 1.44 mol) and 50% aqueous potassium hydroxide solution (150 mL) were added to ethanol (50 mL).The resulting mixture was heated to reflux for 2 hours.After concentration under vacuum, water was added and stirred to give a white precipitate.After collecting the filter cake by filtration, the crude product of the target product is obtained.The crude product was recrystallized from ethanol to give 4-phenylcyclohexanone oxime 1 (106 g, 0.56 mol).It is a white solid.
With hydroxylamine hydrochloride; sodium acetate In methanol; water at 20℃; for 1h;

  • 6
  • [ 4500-20-3 ]
  • [ 21060-33-3 ]
YieldReaction ConditionsOperation in experiment
With peracetic acid; sodium dihydrogenphosphate; sulfuric acid; acetic acid; urea In acetonitrile Heating;
  • 7
  • [ 4500-20-3 ]
  • [ 21060-33-3 ]
  • [ 21060-32-2 ]
YieldReaction ConditionsOperation in experiment
With peracetic acid; sodium dihydrogenphosphate; sulfuric acid; acetic acid; urea In acetonitrile Heating;
  • 9
  • [ 4500-20-3 ]
  • [ 98-88-4 ]
  • [ 5769-30-2 ]
  • <i>N</i>-(<i>trans</i>-4-phenyl-cyclohexyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
(i) H2, Raney-Ni, (ii) /BRN= 471389/; Multistep reaction;
  • 10
  • [ 4500-20-3 ]
  • [ 98-88-4 ]
  • <i>N</i>-(<i>trans</i>-4-phenyl-cyclohexyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
(i) H2, Raney-Ni, (ii) /BRN= 471389/; Multistep reaction;
  • 11
  • [ 4500-20-3 ]
  • [ 75-36-5 ]
  • (R,S)-4-phenylcyclohexanone oxime acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In diethyl ether at 0℃; for 1h;
YieldReaction ConditionsOperation in experiment
Rk.m.Na/EtOH;
Rk.m.H2/PtO2;
Hydr. m. Raney-Ni W4, 100grad, 100at -> 65percent cis-4-Phenyl-cyclohexylamin, 35percent trans-Isomeres;
Δ, Na, abs. A. -> trans-4-Phenylcyclohexylamin;

YieldReaction ConditionsOperation in experiment
99%
  • 15
  • [ 4500-20-3 ]
  • [ 4894-75-1 ]
YieldReaction ConditionsOperation in experiment
95% With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate at 20℃; for 0.0119444h;
95% With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In dichloromethane for 0.0119444h; Irradiation;
95% With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 0.666667h; Heating;
88% Stage #1: 4-phenylcyclohexanone oxime With 4-cyano-3-fluorophenoxymethyl-Merrifield's resin; potassium <i>tert</i>-butylate In tetrahydrofuran; dimethyl sulfoxide at 55℃; for 4h; Stage #2: With trifluoroacetic acid In water at 55℃; for 1h; Further stages.;
85% With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 0.666667h; Heating;
80% With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In dichloromethane for 0.0666667h; microwave irradiation;
75% With ammonium dichromate(VI); water; silica gel; zirconium(IV) chloride at 80℃; for 0.5h;

  • 16
  • [ 4500-20-3 ]
  • [ 94610-82-9 ]
  • [ 499137-81-4 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 1h;
  • 17
  • [ 4500-20-3 ]
  • 4-(dimethyl-aminocarbonyl)-2-fluorobenzonitrile [ No CAS ]
  • 4-cyano-<i>N</i>,<i>N</i>-dimethyl-3-(4-phenyl-cyclohexylideneaminooxy)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 1h;
  • 18
  • 4-phenyl-cyclohexanol [ No CAS ]
  • [ 4500-20-3 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 4-phenyl-cyclohexanol With chromium(VI) oxide; aluminum oxide; <i>tert</i>-butyl alcohol for 0.166667h; Stage #2: With hydroxylamine hydrochloride for 0.116667h;
  • 19
  • [ 4500-20-3 ]
  • [ 593-56-6 ]
  • [ 476373-78-1 ]
YieldReaction ConditionsOperation in experiment
96% With pyridine In ethanol at 20℃;
  • 20
  • [ 4500-20-3 ]
  • [ 541-41-3 ]
  • [ 920743-04-0 ]
YieldReaction ConditionsOperation in experiment
96% With TEA In tetrahydrofuran at 0℃;
  • 21
  • [ 4500-20-3 ]
  • [ 98-88-4 ]
  • C19H19NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iron In tetrahydrofuran at 20℃;
  • 22
  • [ 4500-20-3 ]
  • trans-N-(Diphenylphosphinyl)-4-phenylcyclohexylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2; petroleum ether / 2 h / -50 °C 2: LiBH(s-Bu)3 / tetrahydrofuran / 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2; petroleum ether / -40 °C 2: NaBH4 / tetrahydrofuran / Ambient temperature
  • 23
  • [ 4500-20-3 ]
  • [ 115668-04-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2; petroleum ether / 2 h / -50 °C 2: LiBH(s-Bu)3 / tetrahydrofuran / 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2; petroleum ether / -40 °C 2: NaBH4 / tetrahydrofuran / Ambient temperature
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2; petroleum ether / -40 °C 2: 85 percent / LiBH(sec-C4H9)3 / tetrahydrofuran / Ambient temperature
  • 24
  • [ 4500-20-3 ]
  • (-)-4-phenylcyclohexanone oxime 5-phenylvalerate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: DCC / CH2Cl2
  • 25
  • [ 4500-20-3 ]
  • [ 82543-05-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: B2H6 / tetrahydrofuran / 4 h / Ambient temperature 2: NaHCO3 aq. / diethyl ether / 0.25 h
  • 26
  • [ 4500-20-3 ]
  • [ 5992-23-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C
  • 27
  • [ 4500-20-3 ]
  • [ 5769-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / ethanol 2: Py
  • 28
  • [ 4500-20-3 ]
  • [ 5769-12-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C 3: Py
  • 29
  • [ 4500-20-3 ]
  • [ 4754-29-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / ethanol 2: benzene
  • 30
  • [ 4500-20-3 ]
  • [ 5769-19-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C 3: benzene
  • 31
  • [ 4500-20-3 ]
  • [ 5769-27-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Na / ethanol 2: Py 3: NaOH / aq. ethanol / Heating
  • 32
  • [ 4500-20-3 ]
  • [ 5769-28-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C 3: Py / benzene 4: NaOH / aq. ethanol / Heating
  • 33
  • [ 4500-20-3 ]
  • [ 4795-58-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / ethanol 2: benzene
  • 34
  • [ 4500-20-3 ]
  • [ 4754-30-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C 3: benzene
  • 35
  • [ 4500-20-3 ]
  • [ 5992-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / ethanol 2: benzene
  • 36
  • [ 4500-20-3 ]
  • [ 5769-22-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C 3: Py / benzene
  • 37
  • [ 4500-20-3 ]
  • [ 5769-25-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Na / ethanol 2: Py
  • 38
  • [ 4500-20-3 ]
  • [ 5740-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) H2, Raney-Ni, (ii) /BRN= 471389/ 2: KOH / aq. ethanol / 180 °C 3: Py / benzene
  • 39
  • aluminum nickel [ No CAS ]
  • [ 4500-20-3 ]
  • 4-phenylcyclohexylamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In 1,4-dioxane; methanol; ethanol 34.2 Preparation of (4-[1-((3S)-3-methylpiperazinyl)(1Z)-2-aza-2-(4-phenylcyclohexyl)vinyl]amino}phenyl)-N-[2-(2,4-dichlorophenyl)ethyl]carboxamide Step 2. Preparation of 4-phenylcyclohexylamine. A mixture of 1-(hydroxyimino)-4-phenylcyclohexane (17.4 mmol) and Raney Nickel (300 mg) in ethanol was hydrogenated (90 psi) at 50° C. for 40 hours. The mixture was filtered through a pad of Celite, washed with MeOH, and concentrated. The residue was dissolved in MeOH, treated with HCl (4 N in dioxane, 20 mmol), and concentrated to give 4-phenylcyclohexylamine hydrochloride (100%).
  • 40
  • aqueous potassium hydroxide [ No CAS ]
  • [ 4894-75-1 ]
  • [ 4500-20-3 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride In ethanol 77 Example 77 Example 77 4-phenylcyclohexanone oxime A mixture of 8.08 g. of 4-phenylcyclohexanone (obtained as in Example 76), 8 g. of hydroxylamine hydrochloride and 16 ml. of 45% aqueous potassium hydroxide solution in 100 ml. of ethanol, is heated at reflux for about 4 hours. The mixture is concentrated under vacuum and then diluted with water. The precipitated solid is collected on a filter and recrystallized from Skellysolve B to give 7.5 g. of 4-phenylcyclohexanone oxime having a melting point of 110° to 112° C. Anal. Calcd. for C12 H15 NO: C, 76.15; H, 7.99; N, 7.40. Found: C, 75.91; H, 8.04; N, 7.24.
  • 41
  • [ 4500-20-3 ]
  • [ 108-24-7 ]
  • [ 1006692-57-4 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 4-phenylcyclohexanone oxime; acetic anhydride With triethylphosphine In toluene for 22h; Heating; Stage #2: With potassium carbonate In methanol at 20℃; for 0.5h; Further stages.;
  • 43
  • [ 4500-20-3 ]
  • [ 19992-45-1 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogensulfate monohydrate; molybdenum(V) chloride; sodium cyanoborohydride In ethanol for 0.7h; Reflux;
92% With sodium tetrahydroborate at 20℃; for 0.0333333h; neat (no solvent, solid phase);
85% With iron oxide; zirconium(IV) chloride; sodium cyanoborohydride In neat (no solvent) at 20℃; for 0.0833333h; A typical procedure for solvent-free reductionof benzaldehyde oxime to benzylamine with NaBH3CN/ZrCl4/nano Fe3O4 system General procedure: A mixture of benzaldehyde oxime (0.121 g, 1 mmol) and nano Fe3O4 (0.046 g, 0.2 mmol) (nano particle size≈70 nm) was ground in a porcelain mortar. ZrCl4 (0.233 g,1 mmol) was then added and grinding the mixture was continued for a moment at room temperature. The mortar was heated in an oil bath until the temperature of reaction mixture reaches 75-80 °C. NaBH3CN (0.314 g, 5 mmol) wasthen added portion wisely and the mixture was ground for15 min at 75-80 °C. After completion of the reaction, H2O(5 mL) was added and the mixture was stirred for 5 min. The mixture was extracted with EtOAc (2 × 5 mL) and then dried over anhydrous Na2SO4. Evaporation of the solvent affords the pure liquid benzylamine in 93 % yield (0.1 g, Table 2, entry 1).
85% With zirconium(IV) chloride; sodium cyanoborohydride In neat (no solvent) at 20℃; for 0.0833333h;

  • 44
  • [ 4500-20-3 ]
  • (4-phenylpiperidin-1-yl)(pyridin-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: sodium hydroxide / ethanol / 12 h / 120 °C / Sealed tube 3: thionyl chloride / 0.5 h / 0 °C 4: triethylamine / dichloromethane / 0.5 h / 0 °C 5: sodium hydroxide / methanol / 0.5 h 6: dmap; copper(II) trifluoroacetate; iodosylbenzene / dichloromethane / 4 h / 100 °C / Sealed tube
  • 45
  • [ 4500-20-3 ]
  • C12H16NO2(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: sodium hydroxide / ethanol / 12 h / 120 °C / Sealed tube
  • 46
  • [ 4500-20-3 ]
  • C14H21NO2*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: sodium hydroxide / ethanol / 12 h / 120 °C / Sealed tube 3: thionyl chloride / 0.5 h / 0 °C
  • 47
  • [ 4500-20-3 ]
  • C20H24N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: sodium hydroxide / ethanol / 12 h / 120 °C / Sealed tube 3: thionyl chloride / 0.5 h / 0 °C 4: triethylamine / dichloromethane / 0.5 h / 0 °C
  • 48
  • [ 4500-20-3 ]
  • 4-phenyl-6-(picolinamido)hexanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: sodium hydroxide / ethanol / 12 h / 120 °C / Sealed tube 3: thionyl chloride / 0.5 h / 0 °C 4: triethylamine / dichloromethane / 0.5 h / 0 °C 5: sodium hydroxide / methanol / 0.5 h
  • 49
  • [ 4500-20-3 ]
  • 1-(perfluorobenzoyl)-5-phenyl-6,7-dihydro-1H-azepin-2(5H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: triethylamine / dichloromethane / 13 h / 0 - 20 °C 3: 2,5-di-tert-butyl-p-benzoquinone; palladium(II) trifluoroacetate; racemic methyl phenyl sulfoxide; zinc(II) trifluoroacetate; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane; 1,4-dioxane / 24 h / 20 °C / Inert atmosphere; Sealed tube
  • 50
  • [ 4500-20-3 ]
  • 1-(perfluorobenzoyl)-5-phenylazepan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 1,4-dioxane / 0.5 h / 20 °C 2: triethylamine / dichloromethane / 13 h / 0 - 20 °C
  • 51
  • [ 4500-20-3 ]
  • [ 92-67-1 ]
YieldReaction ConditionsOperation in experiment
93% With Pd(OH)x/LDH In N,N-dimethyl acetamide at 130℃; for 3h; Schlenk technique; Inert atmosphere;
  • 52
  • [ 4500-20-3 ]
  • [ 5769-10-8 ]
  • [ 5992-23-4 ]
YieldReaction ConditionsOperation in experiment
18 % de With sodium tetrahydroborate; molybdenum(VI) oxide In methanol at 0℃; for 2h; Overall yield = 67 mg;
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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 • Beckmann Rearrangement • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs 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 • 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 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 • 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 • 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 • Neber Rearrangement • 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 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 • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • 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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