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[ CAS No. 13026-12-5 ] {[proInfo.proName]}

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Chemical Structure| 13026-12-5
Chemical Structure| 13026-12-5
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Product Details of [ 13026-12-5 ]

CAS No. :13026-12-5 MDL No. :MFCD00014317
Formula : C13H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 198.22 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 13026-12-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.62
TPSA : 37.3 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) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 3.12
Log Po/w (WLOGP) : 2.83
Log Po/w (MLOGP) : 2.84
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.0797 mg/ml ; 0.000402 mol/l
Class : Soluble
Log S (Ali) : -3.57
Solubility : 0.0531 mg/ml ; 0.000268 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.54
Solubility : 0.057 mg/ml ; 0.000288 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 13026-12-5 ]

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 [ 13026-12-5 ]

* 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 [ 13026-12-5 ]

[ 13026-12-5 ] Synthesis Path-Downstream   1~94

  • 2
  • [ 110-89-4 ]
  • [ 141-82-2 ]
  • [ 66-77-3 ]
  • [ 13026-12-5 ]
  • 5
  • [ 104-76-7 ]
  • [ 13026-12-5 ]
  • (+/-)-3<i>t</i>-[1]naphthyl-acrylic acid-(2-ethyl-hexyl ester) [ No CAS ]
  • 7
  • [ 890-50-6 ]
  • [ 13026-12-5 ]
  • 8
  • [ 116659-84-8 ]
  • [ 13026-12-5 ]
  • 9
  • [ 13026-12-5 ]
  • [ 21658-35-5 ]
  • 10
  • [ 13026-12-5 ]
  • [ 3243-42-3 ]
YieldReaction ConditionsOperation in experiment
palladium; In tetrahydrofuran; a) 3-(1-naphthyl)propanoic acid 10% Palladium on carbon (1.00 g) was added to a suspension of 3-(1-naphthyl)acrylic acid (50.0 g) in tetrahydrofuran (500 ml). The mixture was hydrogenated at 6 atmospheres for 18 hours then filtered through a kieselguhr pad washing with ethyl acetate (3*100 ml). The filtrate was evaporated under reduced pressure to give the subtitle compound (50.0 g) as a solid. 1H NMR (DMSO-D6) delta2.65 (2H, t); 3.30 (2H, t); 7.37-7.46 (2H, m); 7.49-7.60 (2H, m); 7.79 (1H, d); 7.93 (1H, d); 8.07 (1H, d); 12.10 (1H, s, br).
With hydrogen; 3- (1-Naphthyl) -propionic acid (5C) was synthesized by hydrogenation of 3- (1-naphthyl) -acrylic acid
  • 11
  • [ 13026-12-5 ]
  • [ 27653-22-1 ]
  • 12
  • [ 13026-12-5 ]
  • [ 97352-00-6 ]
YieldReaction ConditionsOperation in experiment
89% With copper(II) nitrate trihydrate; trimethylsilyl bromide; In acetonitrile; at 50℃; for 2h; General procedure: In a pressure tube, to a solution of alpha,beta-unsaturated carboxylic acid (0.5 mmol, 1 equiv) and copper(II) nitrate trihydrate (60.4 mg, 0.25 mmol, 0.5 equiv) in 3 mL dry acetonitrile, bromotrimethylsilane (306.18 mg, 2 mmol, 4 equiv) was added. The reaction mixture was stirred vigorously at 50C for 2 h (in case of ortho substituted compounds, the reaction mixture was stirred for 3 h). After neutral aqueous work-up, organics were extracted by dichloromethane. Organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure. Upon recrystallization from hexane, the corresponding products were obtained in pure form in good yields.
  • 13
  • [ 13026-12-5 ]
  • (2<i>RS</i>:3<i>SR</i>)-2.3-dihydroxy-3-(naphthyl-(1))-propionic acid [ No CAS ]
  • 14
  • [ 13026-12-5 ]
  • 3<i>t</i>-(4.5-dinitro-naphthyl-(1))-acrylic acid [ No CAS ]
  • 16
  • [ 13026-12-5 ]
  • [ 53248-85-4 ]
  • [ 53248-84-3 ]
  • 17
  • [ 13026-12-5 ]
  • [ 120681-10-9 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 80℃; for 4h; General procedure: The starting materials (acids 7-19) for the synthesis of amides should be activated in the first procedure: the compounds 7-19 (1.0 mM) and SOCl2 (6-10 mL) were mixed and stirred at reflux 80Cfor 4 h. The reaction mixture was cooled and evaporated to give reactive acyl chloride obtained as an oil, which would be dissolved in ethyl acetate (5-6 mL) in the next step.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere; Cooling with ice; General procedure: Conjugated acid 4a (1 gm, 5.5 mmol) was dissolved in 15 mL dry DCM. 2 drops of DMF was added to the solution. Then, oxalyl chloride (0.6 mL, 6.5 mmol) was added at a time under ice cooled condition and stirred at room temperature for 1 h. Then solvent was removed in reduced pressure to remove the excess oxalyl chloride. The resulted acid chloride was dissolved in dry DCM and Et3N (1.5 mL, 11 mmol) was added at ice cooled condition. Then amino acid ester (1.5 gm, 16.38 mmol), dissolved in DCM was added to the reaction mixture and stirred for 30 min at 0 C. The reaction mixture was washed with water and solvent was removed to get a solid mass, which was purified by column chromatography using 20% pet-ether/EtOAC to get compound 11a.Similar procedure was followed for the synthesis of compounds 5b-d.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at -10℃; General procedure: The corresponding acrylic acid was suspended in 30 mL CH2Cl2 with some drops of DMF and the solution was cooled to -10 C. Oxalyl chloride (1.1 equivalents) was added dropwise and the solution was stirred for 1h. The solvent was evaporated under reduced pressure. The residual oil was diluted with 10 mL CH2Cl2 and added to N,O-dimethylhydroxylamine hydrochloride (2 equivalents) in 20 mL CH2Cl2/H2O mixture (1/1) in the presence of Na2CO3. The mixture was stirred for 1 h and the organic solution was washed several times with water, dried over MgSO4 and concentrated under vacuum. The crude material was used in the next step without purification. The following compounds were obtained according to this process:
  • 18
  • [ 860366-20-7 ]
  • [ 13026-12-5 ]
  • 19
  • [ 141-82-2 ]
  • [ 66-77-3 ]
  • [ 13026-12-5 ]
YieldReaction ConditionsOperation in experiment
81% With piperidine; pyridine; at 110℃; General procedure: To a solution of pyridine (3 vol), was added aldehyde (1 mmol) malonic acid (2 mmol)followed by catalytic amount of piperidine (0.1 mmol). The reaction mass was slowly heatedto 110 0C and maintained for 10 - 12 hr at 110 0C. Reaction was monitored by TLC. Reactionmass was cooled to room temperature and quenched into 10 vol of water of pyridine. To thequenched mass was added, NaOH (2 mmol). Reaction mixture was stirred to obtain clearsolution. Then reaction mixture was washed with ethyl acetate (20 vol X 2). Aqueous layerwas then acidified with 50 % sulfuric acid till pH 2.The precipitated solid was filtered andwashed with water (5 vol X 2) followed by pet ether wash 2 vol. The product was suck driedon buchner funnel for 15 min to 60 min. The solid product was dried in oven at 50 to 60 Covernight. Cinnamic acids were obtained in 80 - 90 % yield.
With piperidine; pyridine; at 80℃; for 24h; General procedure: The starting materials (acids 7-19) for the synthesis of amides should be activated in the first procedure: the compounds 7-19 (1.0 mM) and SOCl2 (6-10 mL) were mixed and stirred at reflux 80Cfor 4 h. The reaction mixture was cooled and evaporated to give reactive acyl chloride obtained as an oil, which would be dissolved in ethyl acetate (5-6 mL) in the next step.A solution of acyl chloride (1.0 mM) in ethyl acetate was added dropwise to compounds 5 or 6 (0.5 mM) in ethyl acetate containing potassium carbonate (600 mg) at 0 C with constant stirring overnight. The reaction mixture was then poured in excess of diluted NaOH and extracted with EtOAc .The extraction liquid was purified by a flash chromatography with EtOAc/petroleum ether (3:1, v/v) to give these cinnamamides as follows: the yields were between 40% and 60%.
  • 20
  • [ 66-77-3 ]
  • [ 141-78-6 ]
  • [ 13026-12-5 ]
  • 21
  • [ 64-17-5 ]
  • [ 13026-12-5 ]
  • [ 93863-58-2 ]
  • [ 93863-60-6 ]
  • 22
  • [ 593-77-1 ]
  • [ 13026-12-5 ]
  • [ 105847-24-3 ]
  • 23
  • [ 13026-12-5 ]
  • [ 52031-69-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine; oxalyl dichloride In dichloromethane at 0℃;
With oxalyl dichloride; N,N-dimethyl-formamide In 3-methyl-phenol at 20℃; for 2h; 2.1 (1) To a 50OmL round-bottomed flask, 2g of 3 -naphthalene- 1-yl acrylic acid was added and dissolved in 200ml metacresol, followed by the addition of 2ml of oxalyl chloride and stirring of the mixture. Then, two or three drops of N, N- dimethylformamide (DMF) were added thereto and the mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure to remove volatile compounds. As a result, the yellow compound of 3-naphthalen-l- yl-acryloyl chloride was obtained.
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.2h;
  • 26
  • [ 13026-12-5 ]
  • [ 93863-58-2 ]
  • [ 93863-60-6 ]
  • 29
  • [ 13026-12-5 ]
  • [ 908093-98-1 ]
  • (E)-3-Naphthalen-1-yl-acrylic acid benzhydryl ester [ No CAS ]
  • 30
  • [ 867-13-0 ]
  • [ 66-77-3 ]
  • [ 13026-12-5 ]
  • 31
  • [ 108-24-7 ]
  • [ 66-77-3 ]
  • [ 13026-12-5 ]
  • 32
  • [ 13026-12-5 ]
  • [ 74-89-5 ]
  • [ 51557-25-6 ]
  • 33
  • [ 134-32-7 ]
  • [ 292638-85-8 ]
  • [ 13026-12-5 ]
  • 34
  • [ 13026-12-5 ]
  • α-(dibromomethyl)-1-naphthylmethanol [ No CAS ]
  • 35
  • [ 13026-12-5 ]
  • sodium amalgam [ No CAS ]
  • [ 3243-42-3 ]
  • 36
  • [ 13026-12-5 ]
  • [ 7697-37-2 ]
  • 3<i>t</i>-(4.5-dinitro-naphthyl-(1))-acrylic acid [ No CAS ]
  • 37
  • (+-)-<bromo-(naphthyl-(1))-methyl>-malonic acid [ No CAS ]
  • [ 13026-12-5 ]
  • 38
  • <naphthyl-(1)-methylene>-malonic acid [ No CAS ]
  • [ 13026-12-5 ]
  • 39
  • [ 110-16-7 ]
  • diazotized naphthyl-(1)-amine [ No CAS ]
  • [ 13026-12-5 ]
  • 40
  • [ 79-10-7 ]
  • diazotized naphthyl-(1)-amine [ No CAS ]
  • [ 13026-12-5 ]
  • 41
  • <i>N</i>-<1>naphthylmethylen-<i>o</i>-anisidine [ No CAS ]
  • [ 13026-12-5 ]
  • 42
  • [ 13026-12-5 ]
  • [ 7697-37-2 ]
  • [ 53248-85-4 ]
  • [ 53248-84-3 ]
  • 43
  • [ 13026-12-5 ]
  • [ 77150-88-0 ]
YieldReaction ConditionsOperation in experiment
28% With ammonium bromide; In water; acetonitrile; at 75℃; for 1h;Electrochemical reaction; General procedure: Substrate 1 (0.5mmol), NH4Br (3mmol) were added to an undivided cell which equipped with platinum anode and cathode. Followed by addition of MeCN (7mL) and H2O (3mL). The mixture was electrolyzed under continuous stirring at 75C under a constant current of 40mA for 1h. The solution was cooled to r.t., condensed under vacuum, extracted with DCM (3×10mL), washed with saturated sodium chloride solution. And the organic layers were dried over Na2SO4, filtered and evaporated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=50:1-30:1) to afford the desired product 3.
  • 45
  • [ 13026-12-5 ]
  • N-lithium 2-oxazolidinone [ No CAS ]
  • [ 261768-45-0 ]
  • 46
  • [ 139387-23-8 ]
  • [ 13026-12-5 ]
  • 47
  • sodium; hydroxy-naphthalen-1-yl-methanesulfonate [ No CAS ]
  • [ 141-82-2 ]
  • [ 13026-12-5 ]
  • 48
  • [ 13026-12-5 ]
  • [ 541-41-3 ]
  • [ 98978-43-9 ]
  • 49
  • [ 13026-12-5 ]
  • [ 149107-84-6 ]
  • C54H72O11Si2 [ No CAS ]
  • 50
  • [ 13026-12-5 ]
  • [ 4735-49-3 ]
YieldReaction ConditionsOperation in experiment
98% With chloro-trimethyl-silane; copper(II) nitrate trihydrate; In acetonitrile; at 100℃; for 2h; General procedure: In a pressure tube, to a solution of alpha,beta-unsaturated carboxylic acid (0.5 mmol, 1 equiv) and copper(II) nitrate trihydrate (423 mg, 1.75 mmol, 3.5 equiv) in dry acetonitrile (3 mL), chlorotrimethylsilane (65 mg, 0.6 mmol, 1.2 equiv) was added. The reaction mixture was stirred vigorously at 100 C for 2 h. The reaction was quenched with saturated sodium bicarbonate solution and organics were extracted using dichloromethane. Organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure, giving the corresponding products in pure form in excellent yields.
  • 51
  • [ 201230-82-2 ]
  • [ 77150-88-0 ]
  • [ 13026-12-5 ]
  • 52
  • [ 90-14-2 ]
  • [ 292638-85-8 ]
  • [ 13026-12-5 ]
  • 53
  • [ 13026-12-5 ]
  • C13H11NO2 [ No CAS ]
  • 54
  • [ 13026-12-5 ]
  • C34H46N7O17P3S [ No CAS ]
  • 55
  • [ 13026-12-5 ]
  • C42H44O11 [ No CAS ]
  • 56
  • [ 13026-12-5 ]
  • [ 77150-84-6 ]
  • 57
  • [ 3177-49-9 ]
  • potassium copper (I)-cyanide [ No CAS ]
  • [ 13026-12-5 ]
  • 58
  • 1-naphthalenediazonium tetrachlorocuprate(II) [ No CAS ]
  • [ 13026-12-5 ]
  • 59
  • [ 13026-12-5 ]
  • (1S,2S,3S,4R)-3-Naphthalen-1-yl-bicyclo[2.2.1]heptane-2-carboxylic acid [ No CAS ]
  • 60
  • [ 13026-12-5 ]
  • Dimethyl-((1R,2R,3R,4S)-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-ylmethyl)-amine [ No CAS ]
  • 61
  • [ 13026-12-5 ]
  • (1S,2S,3S,4R)-3-Naphthalen-1-yl-bicyclo[2.2.1]heptane-2-carboxylic acid dimethylamide [ No CAS ]
  • 62
  • [ 13026-12-5 ]
  • 3-((1R,2S,3S,4S)-3-Naphthalen-1-yl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one [ No CAS ]
  • 63
  • [ 13026-12-5 ]
  • 3-((1S,2S,3S,4R)-3-Naphthalen-1-yl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one [ No CAS ]
  • 64
  • [ 13026-12-5 ]
  • 3-((1S,2S,3S,4R)-3-Naphthalen-1-yl-bicyclo[2.2.1]heptane-2-carbonyl)-oxazolidin-2-one [ No CAS ]
  • 65
  • [ 13026-12-5 ]
  • <i>N</i>-[3-benzoyl-4-(2-<i>p</i>-tolyl-acetylamino)-phenyl]-3-naphthalen-1-yl-acrylamide [ No CAS ]
  • 66
  • [ 13026-12-5 ]
  • [ 261768-45-0 ]
  • 68
  • [ 13026-12-5 ]
  • 2-(1'-naphthalenyl)ethen-1-yl-oxirane [ No CAS ]
  • 69
  • [ 13026-12-5 ]
  • [ 160913-07-5 ]
  • 70
  • [ 13026-12-5 ]
  • 1-(isopropylamino)-4-(1'-naphthalenyl)but-3-ene-2-ol [ No CAS ]
  • 76
  • [ 13026-12-5 ]
  • (1R,4aS,8aR)-3-(Decahydro-naphthalen-1-yl)-propionic acid ethyl ester [ No CAS ]
  • 77
  • [ 13026-12-5 ]
  • [ 110105-26-5 ]
  • 80
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-[1]naphthyl)-acryloyl chloride [ No CAS ]
  • 81
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-[1]naphthyl)-acrylic acid methyl ester [ No CAS ]
  • 82
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-[1]naphthyl)-acrylic acid-(3-chloro-propyl ester) [ No CAS ]
  • 83
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-[1]naphthyl)-acrylic acid cyclohexyl ester [ No CAS ]
  • 84
  • [ 13026-12-5 ]
  • (+/-)-3<i>t</i>-(5-nitro-[1]naphthyl)-acrylic acid-(3-dimethylamino-1-methyl-propylamide) [ No CAS ]
  • 85
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-[1]naphthyl)-acrylic acid-(3-diethylamino-propyl ester) [ No CAS ]
  • 86
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-[1]naphthyl)-acrylic acid amide [ No CAS ]
  • 87
  • [ 13026-12-5 ]
  • [ 118664-31-6 ]
  • 90
  • [ 13026-12-5 ]
  • 3<i>t</i>-(4-nitro-naphthyl-(1))-acrylic acid-chloride [ No CAS ]
  • 91
  • [ 13026-12-5 ]
  • 3<i>t</i>-(5-nitro-naphthyl-(1))-acrylic acid ethyl ester [ No CAS ]
  • 92
  • [ 13026-12-5 ]
  • 3<i>t</i>-(4-nitro-naphthyl-(1))-acrylic acid ethyl ester [ No CAS ]
  • 93
  • [ 13026-12-5 ]
  • 3<i>t</i>-(4-acetylamino-naphthyl-(1))-acrylic acid ethyl ester [ No CAS ]
  • 94
  • [ 13026-12-5 ]
  • 3<i>t</i>-(4.5-dinitro-naphthyl-(1))-acrylic acid ethyl ester [ No CAS ]
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