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705-60-2

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705-60-2 Usage

Chemical Properties

Yellow crystalline powder

Uses

1-phenyl-2-nitropropene is used in the production of pharmaceuticals, for instance, for drug Adderall, a drug used to treat ADHD and narcolepsy.

Application

(2-Nitropropenyl)benzene is a derivative of styrene (S687790), which exhibits herbicidal and antibacterial properties.

Synthesis Reference(s)

The Journal of Organic Chemistry, 15, p. 8, 1950 DOI: 10.1021/jo01147a002Tetrahedron Letters, 26, p. 1193, 1985 DOI: 10.1016/S0040-4039(00)98431-4

General Description

trans-β-Methyl-β-nitrostyrene (1-phenyl-2-nitropropene), a nitrostyrene derivative is an α,β-disubstituted nitroalkene. It has been synthesized by reacting benzaldehyde with nitroethane and butylamine. Spectroscopic analysis of 1-phenyl-2-nitropropene has been done using FT-IR, FT-Raman, NMR and UV.

Check Digit Verification of cas no

The CAS Registry Mumber 705-60-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 5 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 705-60:
(5*7)+(4*0)+(3*5)+(2*6)+(1*0)=62
62 % 10 = 2
So 705-60-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3/b8-7+

705-60-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Phenyl-2-nitropropene

1.2 Other means of identification

Product number -
Other names 2-NITROPROP-1-ENYLBENZENE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:705-60-2 SDS

705-60-2Synthetic route

Nitroethane
79-24-3

Nitroethane

benzaldehyde
100-52-7

benzaldehyde

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With 3-(diethylamino)propyltrimethoxysilane supported on silica-alumina at 100℃; for 4h;90%
With (2-hydroxyethyl)ammonium formate at 20℃; for 3h; Knoevenagel condensation; Ionic liquid;90%
With aminopropylated nanosilica for 24h; Henry reaction; Reflux;89%
1-phenyl-2-nitro-1-propanol acetate
66618-80-2

1-phenyl-2-nitro-1-propanol acetate

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With dmap In dichloromethane for 3h;88%
Nitroethane
79-24-3

Nitroethane

benzylamine
100-46-9

benzylamine

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With 4-(4-fluorophenyl)naphthalene-1,2-dione; oxygen at 80℃; for 12h;83%
2-methyl-3-phenyl-2-propenal
101-39-3

2-methyl-3-phenyl-2-propenal

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With copper(II) nitrate trihydrate In water; acetonitrile at 130℃; for 12h;39%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With diethyl ether; mixture of gaseous nitrogen oxides
Nitroethane
79-24-3

Nitroethane

benzaldehyde
100-52-7

benzaldehyde

A

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

B

benzamide
55-21-0

benzamide

Conditions
ConditionsYield
With zinc(II) chloride at 130 - 140℃; im geschlossenen Rohr;
(1-Nitro-allyl)-benzene
62753-13-3

(1-Nitro-allyl)-benzene

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With triethylamine
2-phenyl-1-nitroprop-1-ene
25236-39-9

2-phenyl-1-nitroprop-1-ene

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With triethylamine
(1,2-dibromo-2-nitro-propyl)-benzene
19419-13-7

(1,2-dibromo-2-nitro-propyl)-benzene

2-lithio-2-nitropropane
147225-22-7

2-lithio-2-nitropropane

A

2-bromo-2-nitropropane
5447-97-2

2-bromo-2-nitropropane

B

2,3-dimethyl-2,3-dinitrobutane
3964-18-9

2,3-dimethyl-2,3-dinitrobutane

C

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
In dimethyl sulfoxide Ambient temperature;
In dimethyl sulfoxide for 0.166667h; Mechanism; Product distribution; Ambient temperature; also for other 1-aryl-1,2-dibromo-2-nitropropanes, also in the presence of p-dinitrobenzene or di-tert-butyl nitroxide;
Butyl-(2-nitro-1-phenyl-propyl)-amine
135711-45-4

Butyl-(2-nitro-1-phenyl-propyl)-amine

A

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
In acetonitrile at 30℃; Equilibrium constant; other temp.;
2,3-dinitro-3-phenyl propane
90558-08-0

2,3-dinitro-3-phenyl propane

A

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

B

(Z)-(2-nitroprop-2-en-1-yl)benzene
58321-79-2

(Z)-(2-nitroprop-2-en-1-yl)benzene

Conditions
ConditionsYield
With calcium oxide In cyclohexane for 0.75h; Title compound not separated from byproducts;
C15H15NO2S

C15H15NO2S

A

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

B

thiophenol
108-98-5

thiophenol

Conditions
ConditionsYield
In water; acetonitrile at 35℃; Equilibrium constant; Further Variations:; Temperatures;
1-phenylpropene
637-50-3

1-phenylpropene

4.4'-dipropenyl-diphenyl

4.4'-dipropenyl-diphenyl

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 15 percent / N2O4 / CCl4 / 120 h / Ambient temperature
2: aq. CaO / cyclohexane / 0.75 h
View Scheme
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 58 percent / DMAP / diethyl ether / 1.5 h
2: 88 percent / DMAP / CH2Cl2 / 3 h
View Scheme
With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;
benzaldehyde
100-52-7

benzaldehyde

aminoguanidine salt

aminoguanidine salt

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / t-BuOK * t-BuOH (1:1) / 2-methyl-propan-2-ol; tetrahydrofuran / 16 h / 0 °C
2: 58 percent / DMAP / diethyl ether / 1.5 h
3: 88 percent / DMAP / CH2Cl2 / 3 h
View Scheme
Acetic acid 1-methyl-2-nitro-2-phenyl-ethyl ester
62634-68-8

Acetic acid 1-methyl-2-nitro-2-phenyl-ethyl ester

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N
2: Et3N
View Scheme
Multi-step reaction with 2 steps
1: Na2CO3
2: Et3N
View Scheme
benzaldehyde
100-52-7

benzaldehyde

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 16 h / 20 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice
View Scheme
1-phenylpropene
637-50-3

1-phenylpropene

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium chloride; sodium nitrite at 80℃; for 1h; Schlenk technique; Sealed tube; Inert atmosphere;52 %Chromat.
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(Z)-(2-nitroprop-2-en-1-yl)benzene
58321-79-2

(Z)-(2-nitroprop-2-en-1-yl)benzene

Conditions
ConditionsYield
With polimer supported; triphenylphosphine In dichloromethane at 20℃; for 20h;100%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(2-nitropropyl)benzene
17322-34-8

(2-nitropropyl)benzene

Conditions
ConditionsYield
With formic acid; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; triethylamine; N-tosylethylenediamine In ethyl acetate at 28℃; for 0.5h; chemoselective reaction;99%
With benzaldehyde; 1,2-diamino-benzene In butan-1-ol for 6h; Heating;91%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; S-benzyl isothiouronium chloride In methanol at 60℃; Inert atmosphere;90%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(ethoxycarbonylmethyl)dimethylsulfonium bromide
5187-82-6

(ethoxycarbonylmethyl)dimethylsulfonium bromide

ethyl (4SR,5SR)-3-methyl-4-phenyl-4,5-dihydroisoxazole-5-carboxylate 2-oxide

ethyl (4SR,5SR)-3-methyl-4-phenyl-4,5-dihydroisoxazole-5-carboxylate 2-oxide

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃; stereoselective reaction;98%
formaldehyd
50-00-0

formaldehyd

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

thiophenol
108-98-5

thiophenol

2-Methyl-2-nitro-3-phenyl-3-phenylsulfanyl-propan-1-ol
94421-45-1

2-Methyl-2-nitro-3-phenyl-3-phenylsulfanyl-propan-1-ol

Conditions
ConditionsYield
With 1,1,3,3-tetramethylguanidine for 3h; Ambient temperature;97%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide
1195694-52-0

(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide

2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-(tosyl)-4-quinolinyl]-1-phenylethanone

2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-(tosyl)-4-quinolinyl]-1-phenylethanone

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane; toluene at 20℃; for 0.166667h;
Stage #2: 4-methyl-N-(2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide In 1,2-dichloro-ethane; toluene at 20℃; for 12h; Reagent/catalyst; Solvent; enantioselective reaction;
96%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(E)-1-(2-methoxyphenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one

(E)-1-(2-methoxyphenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one

2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-tosyl-4-quinolinyl]-1-(2-methoxyphenyl)ethanone

2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-tosyl-4-quinolinyl]-1-(2-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane; toluene at 20℃; for 0.166667h;
Stage #2: (E)-1-(2-methoxyphenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one In 1,2-dichloro-ethane; toluene at 20℃; for 48h; enantioselective reaction;
96%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-ylidene)-acetic acid ethyl ester
40129-54-2, 112342-27-5

(6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-ylidene)-acetic acid ethyl ester

5,6-Dihydro-8,9-dimethoxy-3-methyl-2-phenylpyrrolo<2,1-a>isochinolin-1-carbonsaeure-ethylester
79823-24-8

5,6-Dihydro-8,9-dimethoxy-3-methyl-2-phenylpyrrolo<2,1-a>isochinolin-1-carbonsaeure-ethylester

Conditions
ConditionsYield
In ethanol for 2h; Heating;95%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide
1195694-52-0

(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide

C31H28N2O5S

C31H28N2O5S

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene With C32H28F6N4O3 In dichloromethane at 20℃; for 0.166667h;
Stage #2: 4-methyl-N-(2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide In dichloromethane at 20℃; for 12h; Reagent/catalyst; enantioselective reaction;
95%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(E)-4,4-dimethyl-1-(2-(tosylamino)phenyl)pent-1-en-3-one

(E)-4,4-dimethyl-1-(2-(tosylamino)phenyl)pent-1-en-3-one

1-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-tosyl-4-quinolinyl]-3,3-dimethyl-2-butanone

1-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-tosyl-4-quinolinyl]-3,3-dimethyl-2-butanone

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane; toluene at 20℃; for 0.166667h;
Stage #2: (E)-4,4-dimethyl-1-(2-(tosylamino)phenyl)pent-1-en-3-one In 1,2-dichloro-ethane; toluene at 20℃; for 24h; enantioselective reaction;
95%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

β-naphthol
135-19-3

β-naphthol

2-methyl-1-phenylnaphtho[2,1-b]furan
110973-39-2

2-methyl-1-phenylnaphtho[2,1-b]furan

Conditions
ConditionsYield
With potassium carbonate In ethanol at 85℃; for 3h; Temperature; Solvent; Reagent/catalyst;95%
With carbonaceous material (C-SO3H) In water at 60℃; for 10h; Green chemistry;70%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

1-phenylpropan-2-one oxime
13213-36-0

1-phenylpropan-2-one oxime

Conditions
ConditionsYield
With hydrogen In ethanol at 60℃; under 15001.5 Torr; for 0.333333h; Autoclave; chemoselective reaction;94%
With sulfuric acid In water; isopropyl alcohol at 10 - 15℃; electrolysis;91%
With sodium stannite In tetrahydrofuran; water for 0.416667h; Ambient temperature;82%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

isobutene
115-11-7

isobutene

6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide
638133-04-7

6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -90℃;94%
With tin(IV) chloride In dichloromethane at -94 - 30℃;
Diels-Alder Cycloaddition;
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

5-methyl-4-phenyl-1H-1,2,3-triazole

5-methyl-4-phenyl-1H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃; for 1h;94%
With sodium azide; benzoic acid at 80℃; for 0.416667h; Microwave irradiation;57%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

4-methyl-5-phenyl-2H-1,2,3-triazole
80569-59-1

4-methyl-5-phenyl-2H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 60℃;94%
With sodium azide; toluene-4-sulfonic acid at 80℃;
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

cyclopentene
142-29-0

cyclopentene

-(3al,7l,7al)-1,2,3,3a,7,7a-hexahydro-6-methyl-7-phenylcyclopent<1,2>oxazine N-oxide
142840-09-3

-(3al,7l,7al)-1,2,3,3a,7,7a-hexahydro-6-methyl-7-phenylcyclopent<1,2>oxazine N-oxide

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -78℃; for 0.75h; Product distribution; Mechanism; other nitroalkenes and cycloalkenes; diastereoselectivity; velocity;93%
With tin(IV) chloride In dichloromethane at -78℃; for 0.75h;93%
With tin(IV) chloride In dichloromethane at -94 - 30℃;
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

N-bromoacetamide
79-15-2

N-bromoacetamide

1-acetylamino-2-bromo-1-phenyl-2-nitropropane
1215288-71-3

1-acetylamino-2-bromo-1-phenyl-2-nitropropane

Conditions
ConditionsYield
With potassium phosphate In dichloromethane at 20℃; for 24h; Michael addition; regiospecific reaction;92%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

methyl 3-(benzylamino)but-2-enoate
72002-24-5, 36244-63-0

methyl 3-(benzylamino)but-2-enoate

methyl 1-benzyl-2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate
1320232-56-1

methyl 1-benzyl-2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate

Conditions
ConditionsYield
In methanol at 120℃; for 7h;92%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(E)-1-(4-chlorophenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one

(E)-1-(4-chlorophenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one

1-(4-chlorophenyl)-2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-(tosyl)-4-quinolinyl]ethanone

1-(4-chlorophenyl)-2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-(tosyl)-4-quinolinyl]ethanone

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane; toluene at 20℃; for 0.166667h;
Stage #2: (E)-1-(4-chlorophenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one In 1,2-dichloro-ethane; toluene at 20℃; for 24h; enantioselective reaction;
92%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

(E)-1-(4-bromophenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one

(E)-1-(4-bromophenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one

1-(4-bromophenyl)-2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-(tosyl)-4-quinolinyl]ethanone

1-(4-bromophenyl)-2-[(2R,3S,4R)-1,2,3,4-tetrahydro-2-phenyl-3-methyl-3-nitro-1-(tosyl)-4-quinolinyl]ethanone

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane; toluene at 20℃; for 0.166667h;
Stage #2: (E)-1-(4-bromophenyl)-3-(2-(tosylamino)phenyl)prop-2-en-1-one In 1,2-dichloro-ethane; toluene at 20℃; for 24h; enantioselective reaction;
92%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

1-(2-methoxyphenyl)-2-methyl-3-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one
1519057-98-7

1-(2-methoxyphenyl)-2-methyl-3-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one

Conditions
ConditionsYield
With L-proline In water at 60℃; for 10h; Green chemistry;92%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Conditions
ConditionsYield
With sodium hypochlorite; C34H33N2O(1+)*Br(1-) In water; toluene at -20℃; Inert atmosphere; enantioselective reaction;92%
2,2,2-trifluorodiazoethane
371-67-5

2,2,2-trifluorodiazoethane

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

5-methyl-4-phenyl-3-(trifluoromethyl)-1H-pyrazole

5-methyl-4-phenyl-3-(trifluoromethyl)-1H-pyrazole

Conditions
ConditionsYield
With sodium phosphate; silver(l) oxide In tetrahydrofuran at 20℃; Schlenk technique; regioselective reaction;92%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

2-amino-1-phenylpropane
60-15-1, 156-34-3, 51-64-9, 300-62-9

2-amino-1-phenylpropane

Conditions
ConditionsYield
With sodium tetrahydroborate; borane-THF In tetrahydrofuran at 25℃; for 144h;91%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating;77%
With lithium aluminium tetrahydride In diethyl ether for 3h; Inert atmosphere; Reflux;77%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

1-benzyl-3-methyl-3-nitro-4-phenylpyrrolidine

1-benzyl-3-methyl-3-nitro-4-phenylpyrrolidine

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene; N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine In acetonitrile Heating; Modular flow reactor;
Stage #2: With silica gel In acetonitrile Modular flow reactor;
91%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

methyl 2-(5-bromo-3-formyl-1H-indol-2-yl)acetate

methyl 2-(5-bromo-3-formyl-1H-indol-2-yl)acetate

methyl 6-bromo-3-methyl-2-phenyl-9H-carbazole-1-carboxylate

methyl 6-bromo-3-methyl-2-phenyl-9H-carbazole-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2-nitroprop-1-enyl)benzene; methyl 2-(5-bromo-3-formyl-1H-indol-2-yl)acetate With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; Green chemistry;
Stage #2: With hydrogenchloride In water at 20℃; Green chemistry;
91%
ethanol
64-17-5

ethanol

(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

1-Ethoxy-1-phenyl-propan-2-one oxime
96301-73-4

1-Ethoxy-1-phenyl-propan-2-one oxime

Conditions
ConditionsYield
With tin(ll) chloride for 0.333333h; Ambient temperature;90%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

ethanethiol
75-08-1

ethanethiol

1-Ethylsulfanyl-1-phenyl-propan-2-one oxime
96301-74-5

1-Ethylsulfanyl-1-phenyl-propan-2-one oxime

Conditions
ConditionsYield
With tin(ll) chloride for 0.333333h; Ambient temperature;90%
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

Ethyl isocyanoacetate
2999-46-4

Ethyl isocyanoacetate

ethyl 4-methyl-3-phenyl-1H-pyrrole-2-carboxylate
124901-12-8

ethyl 4-methyl-3-phenyl-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; isopropyl alcohol at 10 - 20℃;90%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Ambient temperature;54%
With potassium carbonate In tetrahydrofuran at 20℃; for 16h;
(2-nitroprop-1-enyl)benzene
705-60-2

(2-nitroprop-1-enyl)benzene

quinazolin-3-ium-3-yl(tosyl)amide

quinazolin-3-ium-3-yl(tosyl)amide

1-methyl-2-phenylpyrazolo[1,5-c]quinazoline

1-methyl-2-phenylpyrazolo[1,5-c]quinazoline

Conditions
ConditionsYield
In dimethyl sulfoxide at 110℃; for 24h; Mechanism; Solvent; Temperature; Time; Inert atmosphere; Schlenk technique; Sealed tube;90%
In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere;90%

705-60-2Relevant articles and documents

Active Base Hybrid Organosilica Materials based on Pyrrolidine Builder Units for Fine Chemicals Production

Llopis, Sebastián,Velty, Alexandra,Díaz, Urbano

, p. 5012 - 5024 (2021/10/19)

The catalytic activity of “pyrrolidine type” fragments included or anchored in the mesoporous silica supports or polymeric frameworks have been fully reported for enantioselective transformation. Nevertheless, low attention was focused on their catalytic abilities to perform base-catalyzed reaction. Accordingly, hybrid materials including pyrrolidine fragments in the mesoporous silica supports were prepared following different synthesis methods, such as micellar and fluoride sol-gel routes in absence of structural directing agents. Their great catalytic performance was explored for various base-catalyzed reactions to the formation of C?C bond through Knoevenagel, Claisen-Schmidt and Henry condensations under microwave irradiation. The benefits of microwave irradiation combined with suitable catalytic properties of pyrrolidine hybrid materials with strong base sites and high accessibility to active centers, allowed carrying out successfully base-catalyzed condensation reactions for the production of fine chemicals. Moreover, the hybrid catalyst exhibited high selectivity and good stability over different catalytic cycles contributing to environmental sustainability.

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Bai, Rongxian,Gao, Feng,Gu, Yanlong,Li, Minghao

supporting information, p. 7499 - 7505 (2021/10/12)

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.

A diversity-oriented synthesis of polyheterocycles: Via the cyclocondensation of azomethine imine

Ansari, Arshad J.,Pathare, Ramdas S.,Kumawat, Anita,Maurya, Antim K.,Verma, Sarika,Agnihotri, Vijai K.,Joshi, Rahul,Metre, Ramesh K.,Sharon, Ashoke,Pardasani,Sawant, Devesh M.

supporting information, p. 13721 - 13724 (2019/09/16)

Pd-Catalyzed sequential reactions to afford skeletally diverse molecules are described. The reaction involved azomethine imine formation and a cyclocondensation reaction as individual steps. The methodology provides excellent regio- and stereocontrol. Skeletal diversity was ensured by changing the electrophilic counterpart of azomethine imine. Due to its broader diversity and complexity, the DOS methodology is likely to benefit drug discovery and development in the future.

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