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[ CAS No. 30186-39-1 ] {[proInfo.proName]}

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Product Details of [ 30186-39-1 ]

CAS No. :30186-39-1 MDL No. :MFCD00457595
Formula : C11H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :LXEQKKWJDGVPRW-UHFFFAOYSA-N
M.W : 171.20 Pubchem ID :934729
Synonyms :

Calculated chemistry of [ 30186-39-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.16
TPSA : 22.0 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) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.12
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.318 mg/ml ; 0.00186 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.05 mg/ml ; 0.00612 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.0981 mg/ml ; 0.000573 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 30186-39-1 ]

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 [ 30186-39-1 ]

* 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.

  • Downstream synthetic route of [ 30186-39-1 ]

[ 30186-39-1 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 63984-02-1 ]
  • [ 30186-39-1 ]
  • 4-[1-(1-Phenyl-1H-pyrrol-2-yl)-meth-(E)-ylidene]-amino}-butyric acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 5A molecular sieve; triethylamine In chloroform at 25℃; for 4h;
  • 2
  • [ 1779-49-3 ]
  • [ 30186-39-1 ]
  • [ 74304-92-0 ]
YieldReaction ConditionsOperation in experiment
92% With sodium ethanolate In diethyl ether other reagent and solvent;
75% Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Inert atmosphere; Stage #2: N-phenylpyrrole-2-carbaldehyde In tetrahydrofuran; mineral oil at 20 - 60℃; Synthesis of 2- or 3-vinyl-substituted heteroarene (1 or 1’) General procedure: To a suspension of NaH (60% oil suspension, 800 mg, 20.0 mmol) in THF (20 mL) was addedmethyltriphenylphosphonium bromide (3.57 g, 10.0 mmol) at room temperature under argon.After stirring for 2 h, aldehyde derivative (10 mmol) in THF (10 mL) was added dropwise overa period of 10 min. The reaction mixture was warmed to 60 oC and the progress of the reactionwas monitored by TLC. After the reaction was completed, the reaction mixture was cooled toroom temperature and quenched with H2O and THF was removed in vacuo. The residue wasdiluted with EtOAc, and washed with 50% NaHSO4 aq. and 50% Na2CO3 aq. The organic layerwas dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica-gelcolumn chromatography to give the corresponding 2- or 3-vinyl substituted heteroarene (1 or1’)
  • 3
  • [ 30186-39-1 ]
  • [ 29173-25-9 ]
  • [ 118896-46-1 ]
YieldReaction ConditionsOperation in experiment
55% With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;
  • 4
  • [ 30186-39-1 ]
  • [ 120777-22-2 ]
YieldReaction ConditionsOperation in experiment
93% With trifluorormethanesulfonic acid In 1,2-dichloro-ethane for 3h; Heating;
  • 5
  • [ 20432-40-0 ]
  • [ 586-96-9 ]
  • [ 574-85-6 ]
  • [ 36839-03-9 ]
  • [ 30186-39-1 ]
  • [ 525-24-6 ]
YieldReaction ConditionsOperation in experiment
1: 48% 2: 28% 3: 1% With ethanol at 35 - 40℃; for 72h;
In ethanol at 45 - 50℃; for 48h;
With ethanol at 35 - 40℃; for 72h;
  • 6
  • [ 635-90-5 ]
  • [ 68-12-2 ]
  • [ 30186-39-1 ]
YieldReaction ConditionsOperation in experiment
59% Phosphorus oxychloride (0.7 mL, 7.68 mmol) was added slowly to ice-cold dimethylformamide (0.6 mL, 7.68 mmol). The mixture was warmed to room temperature and stirred for 15 min. A solution of <strong>[635-90-5]1-phenylpyrrole</strong> (1.0 g, 6.98 mmol) in ethylene dichloride (5 mL) was added and the reaction mixture heated at reflux for 1 h. The mixture was cooled to 10 0C and quenched into 10% sodium acetate solution (20 mL). The organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to give a crude residue. Purification by column chromatography over silica gel (60-120 mesh) using 2% ethyl acetate in petroleum ether as eluent gave l-phenylpyrrole-2-carbaldehyde (700 mg, 59%) as a colourless oil.
581 mg With trichlorophosphate; at 20 - 50℃; for 3h;Inert atmosphere; Phosphorousoxychloride (1.30 mL, 14.0 mmol) and N,N-dimethylformamide (1.08 mL, 14.0 mmol) were combined at 0 C. under nitrogen, warmed to room temperature and stirred for 15 minutes. To the resulting mixture, a solution of <strong>[635-90-5]1-phenylpyrrole</strong> (2.00 g, 14.0 mmol) in N,N-dimethylformamide (1 mL) was added dropwise by syringe. The reaction was heated to 50 C. for 3 hours, cooled to room temperature, diluted with saturated aqueous bicarbonate, and stirred for 10 minutes. The mixture was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography, eluting with 10% ethyl acetate in hexanes to give <strong>[635-90-5]1-<strong>[635-90-5]phenyl-1H-pyrrole</strong></strong>-2-carbaldehyde (11-1, 581 mg).
  • 7
  • [ 79-24-3 ]
  • [ 30186-39-1 ]
  • [ 174415-44-2 ]
YieldReaction ConditionsOperation in experiment
73% With ammonium acetate at 60℃; for 4h;
  • 8
  • [ 2999-46-4 ]
  • [ 30186-39-1 ]
  • ethyl 3-(N-phenylpyrrol-2-yl)-1H-pyrrole-2,4-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; <i>tert</i>-butyl alcohol at 60℃; for 4h;
  • 9
  • [ 2999-46-4 ]
  • [ 30186-39-1 ]
  • [ 174415-38-4 ]
YieldReaction ConditionsOperation in experiment
58% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; <i>tert</i>-butyl alcohol at 60℃; for 4h;
  • 10
  • [ 30186-39-1 ]
  • [ 141-78-6 ]
  • [ 174415-35-1 ]
YieldReaction ConditionsOperation in experiment
76% With sodium ethanolate In ethanol for 4h; Ambient temperature;
  • 11
  • [ 635-90-5 ]
  • [ 33513-42-7 ]
  • [ 120777-22-2 ]
  • [ 30186-39-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.166667h; Stage #2: 1-phenylpyrrole In dichloromethane at 50℃; for 1h; Stage #3: With sodium hydroxide In dichloromethane at 85 - 90℃; for 0.166667h; Further stages. Title compound not separated from byproducts.;
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.166667h; Stage #2: 1-phenylpyrrole In DMF (N,N-dimethyl-formamide); dichloromethane at 0 - 50℃; for 1.16667h; Stage #3: With sodium hydroxide In DMF (N,N-dimethyl-formamide); dichloromethane; water at 0 - 85℃; for 0.166667h; 1 1-Phenylpyrrole-2-carbaldehyde 1-Phenylpyrrole-2-carbaldehyde In a nitrogen purged one liter flask equipped with a mechanical stirrer were placed 16.2 mL of dimethylformamide followed by slow addition of 19 mL of POCl3. The mixture was stirred for 10 minutes, then cooled to 0° C. To the mixture was added a solution of 25 g of 1-phenylpyrrole in 25 mL of dichloromethane. The mixture was allowed to warm to room temperature (10 minutes) and was then heated to 50° C. for one hour. The contents were then cooled to room temperature and the flask was opened to the air and 220 g of crushed ice were added, followed by 250 mL of 20 percent aqueous NaOH. The mixture was immediately warmed to 85° C. and stirred for 10 minutes, then the flask was cooled to room temperature using an ice bath. The reaction mixture was extracted with dichloromethane (3×100 mL) and the combined organic fractions were washed with water (2×200 mL). The organic fraction was then dried with sodium sulfate and the volatiles removed in a rotary evaporator to leave an orange oil (24.4 g, 82 percent). The product contained 10 percent of the 1-phenylpyrrole-3-carbaldehyde isomer, and was used without further purification. 1H NMR (CDCl3): 6.35 (dd, 1H), 7.0 (t, 1H), 7.1 (dd, 1H), 7.3 (m, 2H), 7.4 (m, 3H), 9.5 (s, 1H); 13C {1H} NMR (CDCl3) 178.4, 138.2, 132.0, 130.6, 128.6, 127.7, 125.5, 121.5, 110.4.
1: 91 %Spectr. 2: 9 %Spectr. Stage #1: 1-phenylpyrrole; N,N-dimethyl-formamide With trichlorophosphate In 1,1-dichloroethane for 1h; Reflux; Stage #2: With potassium hydroxide In 1,1-dichloroethane; water for 0.0166667h;
  • 12
  • [ 30186-39-1 ]
  • [ 107-15-3 ]
  • 1,6-di(1-phenylpyrrol-2-yl)-2,5-diazahexa-1,5-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In methanol at 20℃; for 12h;
  • 13
  • [ 30186-39-1 ]
  • [ 98-88-4 ]
  • [ 501125-36-6 ]
YieldReaction ConditionsOperation in experiment
61% With aluminium trichloride In 1,2-dichloro-ethane for 3h;
  • 14
  • [ 30186-39-1 ]
  • 4-[N-(2,4-dimethylphenyl)-N-phenylamino]benzyl(triphenyl)phosphonium bromide [ No CAS ]
  • cis-N-phenyl-2-{2-[4-(N-(2,4-dimethylphenyl)-N-phenylamino)phenyl]ethenyl}pyrrole [ No CAS ]
  • trans-N-phenyl-2-{2-[4-(N-(2,4-dimethylphenyl)-N-phenylamino)phenyl]ethenyl}pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In tetrahydrofuran at 20℃; for 2h;
  • 15
  • [ 1003-29-8 ]
  • [ 98-80-6 ]
  • [ 30186-39-1 ]
YieldReaction ConditionsOperation in experiment
81% With copper diacetate; triethylamine In dichloromethane at 20℃; for 18h;
  • 16
  • [ 74-90-8 ]
  • [ 30186-39-1 ]
  • hydroxy-(1-phenyl-1<i>H</i>-pyrrol-2-yl)-acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Amberlyst-A21 In various solvent(s) at 20℃;
  • 17
  • [ 151-50-8 ]
  • [ 30186-39-1 ]
  • [ 18162-48-6 ]
  • tert-butyldimethylsilyloxy(N-phenylpyrrol-2-yl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc(II) iodide In acetonitrile at 20℃;
  • 18
  • [ 1003-29-8 ]
  • [ 591-50-4 ]
  • [ 30186-39-1 ]
YieldReaction ConditionsOperation in experiment
89% With potassium phosphate; copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine In toluene at 110℃; for 24h;
  • 19
  • [ 30186-39-1 ]
  • tert-butyldimethylsilyloxy(N-phenylpyrrol-2-yl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Amberlyst-A21 / various solvent(s) / 20 °C 2: imidazole / dimethylformamide / 20 °C
  • 20
  • [ 30186-39-1 ]
  • [ 501125-45-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 61 percent / AlCl3 / 1,2-dichloro-ethane / 3 h 2: 100 percent / K2CO3 / ethanol / 2 h / 70 °C 3: 81 percent / 2N aq. KOH / ethanol / 3 h / 70 °C
  • 21
  • [ 30186-39-1 ]
  • 3-(4-benzoyl-1-phenyl-1<i>H</i>-pyrrol-2-yl)-<i>N</i>-hydroxy-acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 61 percent / AlCl3 / 1,2-dichloro-ethane / 3 h 2: 100 percent / K2CO3 / ethanol / 2 h / 70 °C 3: 81 percent / 2N aq. KOH / ethanol / 3 h / 70 °C 4: Et3N / tetrahydrofuran / 0.17 h 5: 53 percent / NH2OH / tetrahydrofuran / 0.25 h / 20 °C
  • 22
  • [ 30186-39-1 ]
  • [ 501125-40-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 61 percent / AlCl3 / 1,2-dichloro-ethane / 3 h 2: 100 percent / K2CO3 / ethanol / 2 h / 70 °C
  • 23
  • [ 30186-39-1 ]
  • C23H19NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 61 percent / AlCl3 / 1,2-dichloro-ethane / 3 h 2: 100 percent / K2CO3 / ethanol / 2 h / 70 °C 3: 81 percent / 2N aq. KOH / ethanol / 3 h / 70 °C 4: Et3N / tetrahydrofuran / 0.17 h
  • 24
  • [ 30186-39-1 ]
  • methyl 4-methyl-3-(N-phenylpyrrol-2-yl)-1H-pyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / AcONH4 / 4 h / 60 °C 2: 66 percent / DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 4 h / 60 °C
  • 25
  • [ 30186-39-1 ]
  • ethyl 4-methyl-3-(N-phenylpyrrol-2-yl)-1H-pyrrole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / AcONH4 / 4 h / 60 °C 2: 69 percent / DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 4 h / 60 °C
  • 26
  • [ 30186-39-1 ]
  • ethyl 3-(N-phenylpyrrol-2-yl)-1H-pyrrole-2,4-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 58 percent / DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 4 h / 60 °C 2: DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 4 h / 60 °C
Multi-step reaction with 3 steps 1: 76 percent / NaOEt / ethanol / 4 h / Ambient temperature 2: DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 1.) RT, 20 min, 2.) 60 deg C, 4 h 3: DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 4 h / 60 °C
  • 27
  • [ 30186-39-1 ]
  • [ 174415-38-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / NaOEt / ethanol / 4 h / Ambient temperature 2: DBU / tetrahydrofuran; 2-methyl-propan-2-ol / 1.) RT, 20 min, 2.) 60 deg C, 4 h
  • 28
  • [ 30186-39-1 ]
  • [ 118896-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 55 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 2: 1) POCl3 / 1) r.t., 30 min, 2) DMF, 80 deg C
  • 29
  • [ 30186-39-1 ]
  • [ 118896-73-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 55 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 2: 1) POCl3 / 1) r.t., 30 min, 2) DMF, 80 deg C 3: 92 percent / acetonitrile / Heating 4: 92 percent / potassium hydroxide / ethanol / 70 °C
  • 30
  • [ 30186-39-1 ]
  • [ 118896-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 55 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 2: 1) POCl3 / 1) r.t., 30 min, 2) DMF, 80 deg C 3: 92 percent / acetonitrile / Heating
  • 31
  • [ 30186-39-1 ]
  • [ 137965-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 5A molecular sieves, Et3N / CHCl3 / 4 h / 25 °C 2: H2 / PtO2 / methanol / 35 - 39 Torr 3: toluene / 8 h / Heating
  • 32
  • [ 30186-39-1 ]
  • [ 137965-50-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5A molecular sieves, Et3N / CHCl3 / 4 h / 25 °C 2: H2 / PtO2 / methanol / 35 - 39 Torr
  • 33
  • [ 30186-39-1 ]
  • [ 137965-75-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 5A molecular sieves, Et3N / CHCl3 / 4 h / 25 °C 2: H2 / PtO2 / methanol / 35 - 39 Torr 3: toluene / 8 h / Heating 4: 1.) AcOH / 1.) MeOH, H2O, 25 deg C, 5 min, 2.) MeOH, H2O, 25 deg C, overnight
  • 34
  • [ 30186-39-1 ]
  • [ 74809-29-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / NaOEt / diethyl ether / other reagent and solvent 2: 81 percent / CHCl3 / 0.17 h / 5 °C
  • 35
  • [ 30186-39-1 ]
  • [ 74809-24-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / NaOEt / diethyl ether / other reagent and solvent 2: 59 percent / hydroquinone
  • 36
  • [ 635-90-5 ]
  • [ 30186-39-1 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide; trichlorophosphate In dichloromethane; N,N-dimethyl-formamide 5 Synthesis of 1-Phenylpyrrole-2-carbaldehyde Synthesis of 1-Phenylpyrrole-2-carbaldehyde POCl3 (0.70 mol, 65.3 ml) was added dropwise to 76 ml of DMF and stirred for 10 min. The temperature was lowered to 0° C. and a solution of 1-phenylpyrrole (0.70 mol, 100 g) in dichloromethane (100 ml) was added dropwise. The viscous solution was slowly warmed to 50° C. and stirred for 1 h. After cooling to room temperature, the flask was opened to the air and charged with 750 g of crushed ice. A 20 wt % solution of NaOH (885 ml) was added cautiously and the mixture was immediately heated to 90-95° C. and stirred for 10 min. The flask was placed in an ice bath and the product solidified upon cooling. The solids were collected on a filter funnel, washed with water, re-dissolved in dichloromethane, and dried over MgSO4. Evaporation of the solvent yielded 114 g of an orange oil (95% yield). 1H-NMR showed the crude product contained ca. 10% 1-phenylpyrrole-3-carbaldehyde.
With trichlorophosphate In N,N-dimethyl-formamide 87.a a a 2-Formyl-1-phenylpyrrole, 3-formyl-1-phenylpyrrole DMF 561 mg (7.68 mmol) was cooled to 0° C., and added dropwise with POCl3 (1.18 g, 7.68 mmol). The mixture was stirred at room temperature for 15 minutes, and added dropwise with a solution of 1-phenylpyrrole (1.00 g, 6.98 mmol)/DMF (1.6 mL). After stirring at 50° C. for 1.5 hours, the mixture was cooled to 0° C. and added with saturated aqueous Na2CO3 solution to adjust it pH to 8. The mixture was diluted with ethyl acetate and the organic layer was separated. The layer was washed three times with water and dried over Na2SO4. The drying agent was removed by filtration and then the filtrate was concentrated. The residue was separated and purified by silica gel chromatography (dichloromethane/hexane) to obtain the title compound.
With sodium hydroxide; trichlorophosphate In dichloromethane; N,N-dimethyl-formamide 7 1-Phenylpyrrole-2-carbaldehyde 1-Phenylpyrrole-2-carbaldehyde POCl3 (107.3 g, 0.70 mol) was added dropwise to 76 mL of DMF (71.7 g, 0.98 mol) and stirred for 10 min. The temperature was lowered to 0° C. and a solution of 1-phenylpyrrole (100 g, 0.70 mol) in 100 mL of dichloromethane was added slowly. The viscous solution was slowly warmed to 50° C. and stirring continued for 1 h. After cooling to room temperature, the flask was opened to the air and charged with 750 g of crushed ice. A 20 wt % solution of NaOH (885 mL) was added cautiously and the mixture was immediately heated to 85-90° C. and stirred for 10 min. The solvent was distilled off in the process. The flask was placed in an ice bath, cooled to room temperature, and the reaction mixture was extracted with dichloromethane (2*200 mL). The combined organic fractions were washed with water and dried (MgSO4). Evaporation of the solvent yielded 114 g of product as an orange oil containing ca. 10% of the 1-phenylpyrrole-3-carbaldehyde isomer.
  • 37
  • [ 3699-66-9 ]
  • [ 30186-39-1 ]
  • [ 604809-97-4 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran at 0 - 25℃; for 1h; Stage #2: N-phenylpyrrole-2-carbaldehyde In tetrahydrofuran at -10 - 25℃; for 0.666667h; 1 Ethyl-(2Z)-2-methyl-3-[1-phenylpyrrol-2-yl]prop-2-enoate Into a 250 mL flask, a solution of triethyl 2-phosphonopropionate (32 mL, 150 mmoles) in 20 mL of THF was added slowly to a mixture of sodium hydride (4.8 g, 200 mmoles) in 10 mL of THF at 0° C. The slurry was warmed to room temperature and stirred for one hour; the temperature was lowered to -10° C. Then a solution of 1-phenylpyrrole-2-carbaldehyde (24.4 g, 142 mmoles) in 50 mL of THF was added in a period of 10 minutes. The mixture slowly formed a precipitate. The precipitate was partially broken with a spatula and the reaction mixture was slowly warmed to room temperature over 30 minutes. A saturated aqueous solution of NH4Cl (20 mL) was carefully added. The product was extracted in ether (2×100 mL), the ether extracts washed with brine and dried over sodium sulfate. The solvent was removed in a rotary evaporator, and the crude product was washed with hexane to give an orange oil. The oil crystallized over a period of several days and was triturated with small portions of hexane (5×10 mL), filtered and the solid dried in vacuo to give 25.8 g (71 percent) of a light-tan crystalline material. 1H NMR (CDCl3): 7.4 (m, 4H), 7.3 (m, 2H), 7.0 (dd, 1H), 6.7 (dd, 1H), 6.4 (t, 1H), 4.1 (q, 2H), 2.2 (d, 3H), 1.2 (t, 3); 13C {1H} NMR (CDCl3) 168.8, 139.2, 129.6, 129.2, 127.6, 127.5, 126.3, 125.0, 122.9, 114.3, 110.2, 60.4, 14.3, 14.2.
With NaH; ammonium chloride In tetrahydrofuran 5 Synthesis of Ethyl[2Z]-2-methyl-3-[1-phenylpyrrol-2-yl]prop-2-enoate Synthesis of Ethyl[2Z]-2-methyl-3-[1-phenylpyrrol-2-yl]prop-2-enoate Triethyl 2-phosphonopropionate (0.714 mol, 153 ml) was dissolved in THF (75 ml) and added slowly to NaH (1.0 mol, 24.3 g) in THF (60 ml) at 0° C. The mixture was slowly warmed to room temperature and stirring was continued for 1 h after gas evolution had ceased. The temperature was lowered to -10° C. and a solution of the above described 1-Phenylpyrrole-2-carbaldehyde (0.665 mol, 113.0 g) in 200 ml of THF was added dropwise. The flask and contents were warmed to room temperature over a 30 minute period resulting in a thick precipitate which decoupled the magnetic stirrer. A saturated solution of NH4Cl (100 ml) was added cautiously dissolving the precipitate to give a two phase solution. After evaporating the THF, the crude product was extracted with ether (2*200 ml).
  • 38
  • [ 914978-98-6 ]
  • [ 30186-39-1 ]
  • [ 1161408-51-0 ]
YieldReaction ConditionsOperation in experiment
30% With toluene-4-sulfonic acid In N,N-dimethyl-formamide Reflux;
  • 39
  • [ 30186-39-1 ]
  • [ 76457-90-4 ]
  • [ 1161408-50-9 ]
YieldReaction ConditionsOperation in experiment
34% With toluene-4-sulfonic acid In N,N-dimethyl-formamide Reflux;
  • 40
  • [ 30186-39-1 ]
  • [ 151297-83-5 ]
  • [ 1161408-53-2 ]
YieldReaction ConditionsOperation in experiment
45% With toluene-4-sulfonic acid In N,N-dimethyl-formamide Reflux;
  • 41
  • [ 30186-39-1 ]
  • [ 50691-32-2 ]
YieldReaction ConditionsOperation in experiment
66% With potassium hydroxide; hydrazine In ethylene glycol at 20 - 150℃; 254 A mixture of l-phenylpyrrole-2-carbaldehyde (700 mg, 4.1 nunol), potassium hydroxide (490 mg, 12.3 mmol) and hydrazine hydrate (0.8 mL, 12.3 mmol) in ethylene glycol (15 mL) was stirred at ambient temperature for 30 min and then slowly heated to 150 °C and maintained for 2 h. The reaction mixture was allowed to cool to ambient temperature, poured into ice- water and extracted with diethyl ether. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude compound. Purification by column chromatography over silica gel (60-120 mesh) using petroleum ether as eluent to afford 2-methyl-l-phenyl-pyrrole (430 mg, 66%) as a yellow oil.
  • 42
  • [ 635-90-5 ]
  • [ 67-68-5 ]
  • [ 30186-39-1 ]
YieldReaction ConditionsOperation in experiment
29% With 1,4-diaza-bicyclo[2.2.2]octane; oxygen; copper(II) bis(trifluoromethanesulfonate) at 100℃;
  • 43
  • [ 635-90-5 ]
  • [ 2700-30-3 ]
  • [ 120777-22-2 ]
  • [ 30186-39-1 ]
  • 44
  • [ 635-90-5 ]
  • [ 607-00-1 ]
  • [ 120777-22-2 ]
  • [ 30186-39-1 ]
  • 45
  • [ 30186-39-1 ]
  • [ 501-65-5 ]
  • [ 1428368-57-3 ]
YieldReaction ConditionsOperation in experiment
56% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In toluene at 110℃; for 120h; Inert atmosphere; regioselective reaction;
  • 46
  • [ 30186-39-1 ]
  • [ 75-36-5 ]
  • (E)-1-phenyl-1H-pyrrole-2-carbaldehyde O-acetyl oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: N-phenylpyrrole-2-carbaldehyde With hydroxylamine hydrochloride; sodium acetate In ethanol at 100℃; Stage #2: acetyl chloride With triethylamine In dichloromethane at 0 - 20℃;
  • 47
  • [ 23051-44-7 ]
  • [ 30186-39-1 ]
  • 2-(5,5-dimethyl-3-(2-(1-phenyl-1H-pyrrol-2-yl)vinyl)cyclohex-2-enylidene)malononitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With piperidine In ethanol at 60℃; for 20h;
  • 48
  • [ 888705-44-0 ]
  • [ 30186-39-1 ]
  • C25H31N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N1-(2,6-diisopropylphenyl)ethane-1,2-diamine; N-phenylpyrrole-2-carbaldehyde In tetrahydrofuran at 60℃; for 0.0833333h; Stage #2: With formic acid; sodium sulfate In tetrahydrofuran at 20℃; for 18h; Stage #3: With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran; methanol at 20℃; for 6h;
  • 49
  • [ 444325-38-6 ]
  • [ 30186-39-1 ]
  • C22H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-2,4,6-trimethylphenyl-(1,2-diaminoethane); N-phenylpyrrole-2-carbaldehyde In tetrahydrofuran at 60℃; for 0.0833333h; Stage #2: With formic acid; sodium sulfate In tetrahydrofuran at 20℃; for 18h; Stage #3: With toluene-4-sulfonic acid; sodium sulfate In tetrahydrofuran; methanol at 20℃; for 6h;
  • 50
  • [ 30186-39-1 ]
  • [ 74809-39-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere 1.2: 20 - 60 °C 2.1: toluene / 20 - 150 °C / Inert atmosphere 3.1: 10% Ru/C / toluene / 24 h / 110 °C / Inert atmosphere
  • 51
  • [ 30186-39-1 ]
  • [ 74809-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere 1.2: 20 - 60 °C 2.1: toluene / 20 - 150 °C / Inert atmosphere
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