3724-65-0

Basic information

• Product Name: trans-Crotonic acid
• Synonyms: Crotonic acid;3-Methylacrylic acid;Acrylic acid, 3-methyl-;Kyselina krotonova;alpha-Butenoic acid;But-2-enoic acid
• CAS NO: 3724-65-0
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.08924
• EINECS: 203-533-9
• Mol File: 3724-65-0.mol
• Article Data: 40

Chemical Properties

• Melting Point: 73℃
• Boiling Point: 176.974 °C at 760 mmHg
• Flash Point: 81.555 °C
• Appearance: Off-white powder with harsh, pungent and acrylic odour
• Density: 1.04 g/cm³
• Water Solubility: soluble
• CAS DataBase Reference: trans-Crotonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-Crotonic acid(3724-65-0)
• EPA Substance Registry System: trans-Crotonic acid(3724-65-0)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R21/22:; R34:
• Safety Statements: S26:; S36/37/39:; S45:
• Hazardous Substances Data: 3724-65-0(Hazardous Substances Data)

Usage

General Description

Trans-crotonic acid, also known as (E)-2-butenoic acid, is a short-chain unsaturated carboxylic acid with the chemical formula C4H6O2. It is a colorless liquid with a fruity odor and is commonly found in croton oil and other natural sources. Trans-crotonic acid is used in the production of flavors and fragrances, as well as in the synthesis of pharmaceuticals and agrochemicals. It has been found to exhibit antitumor and anti-inflammatory properties, making it a potential candidate for pharmaceutical and medicinal applications. Additionally, trans-crotonic acid has been studied for its potential use in polymer synthesis and as a precursor in organic reactions. Overall, trans-crotonic acid is a versatile compound with a wide range of industrial and medicinal applications.

InChI:InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+

Synthetic route

but-2-enenitrile (4786-20-3) → 2-butenoic acid (3724-65-0)

Conditions	Yield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 12h; pH=7.2;	98%

carbon monoxide (201230-82-2) + allyl alcohol (107-18-6) → 2-butenoic acid (3724-65-0)

Conditions	Yield
1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In 1,2-dimethoxyethane at 190℃; under 30400 Torr; for 48h;	93%

crotonaldehyde (123-73-9) → 2-butenoic acid (3724-65-0)

Conditions	Yield
With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 20h; Kinetics; Concentration; chemoselective reaction;	92%
With (bipyH2)-CrOCl5 In dichloromethane at 28 - 30℃; for 0.5h;	90%
With tert.-butylhydroperoxide; Ammonium iron sulfate In water; dimethyl sulfoxide at 80℃; for 4h; chemoselective reaction;	90%

(E/Z)-2-buten-1-ol (6117-91-5) → 2-butenoic acid (3724-65-0)

Conditions	Yield
With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 31h; chemoselective reaction;	90%
With tert.-butylhydroperoxide; copper(ll) bromide In water; dimethyl sulfoxide for 24h; Inert atmosphere; Reflux; chemoselective reaction;	89%
With sodium hydroxide; hexacyanoferrate(III); sodium ruthenate(VI) In water Thermodynamic data; Kinetics; Mechanism;
With oxygen In toluene at 100℃; under 750.075 Torr; for 0.5h; Catalytic behavior; Reagent/catalyst;
With oxygen In toluene at 80℃; under 750.075 Torr; Catalytic behavior;

2,3-dibromobutanoic acid (600-30-6) → 2-butenoic acid (3724-65-0)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; 1,2-di(thiophen-2-yl)ditelluride In ethanol; water Ambient temperature;	75%

ethyl crotonate (10544-63-5) → 2-butenoic acid (3724-65-0)

Conditions	Yield
With Dowex-50 In water for 12h; Heating;	65%
With sodium hydroxide In methanol; dichloromethane at 20℃; for 0.25h;

3-penten-2-one (625-33-2) → 2-butenoic acid (3724-65-0)

Conditions	Yield
With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry;	58%

shikonin (517-88-4, 517-89-5, 11031-58-6, 54952-43-1, 85921-41-1) + crotonyl chloride (10487-71-5) → 2-butenoic acid (3724-65-0) + Shikonin Crotonate (84273-03-0)

Conditions	Yield
for 12h;	A n/a B 45%

(R)-3-(Tolylthio)butyric acid (141079-81-4) → 2-butenoic acid (3724-65-0) + (R)-3-((R)-Toluene-4-sulfinyl)-butyric acid (141096-33-5) + (R)-3-((S)-Toluene-4-sulfinyl)-butyric acid (110968-84-8)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;	A 2% B 45% C 23.5%

(R)-3-(Phenylthio)buttersaeure (115395-14-7) → 2-butenoic acid (3724-65-0) + (R)-3-<(R)-Phenylsulfinyl>butyric acid (141096-32-4) + (R)-3-<(S)-Phenylsulfinyl>butyric acid (115395-15-8)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;	A 3% B 39% C 11%
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;	A 2% B 11% C 11%

(R)-3-(4-Fluoro-phenylsulfanyl)-butyric acid (141079-82-5) → 2-butenoic acid (3724-65-0) + (R)-3-((R)-4-Fluoro-benzenesulfinyl)-butyric acid (141079-90-5) + (R)-3-((S)-4-Fluoro-benzenesulfinyl)-butyric acid (141079-91-6)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;	A 2% B 38% C n/a

(S)-3-(2-Chloro-phenylsulfanyl)-butyric acid (141079-88-1) → 2-butenoic acid (3724-65-0) + (S)-3-((R)-2-Chloro-benzenesulfinyl)-butyric acid (141080-03-7) + (S)-3-((S)-2-Chloro-benzenesulfinyl)-butyric acid (141080-02-6)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 7 d;	A 29% B 15% C n/a

(R)-3-(Methylthio)butyric acid (141079-84-7) → 2-butenoic acid (3724-65-0) + (R)-3-Methanesulfinyl-butyric acid (141079-94-9, 141079-95-0)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h; Yield given;	A 2% B n/a

(R)-3-(2,6-Dimethyl-phenylsulfanyl)-butyric acid (141079-83-6) → 2-butenoic acid (3724-65-0) + (R)-3-(2,6-Dimethyl-benzenesulfinyl)-butyric acid (141079-92-7, 141079-93-8)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h; Yield given;	A 2% B n/a

(R)-3-(tert-Butylthio)butyric acid (141079-85-8) → 2-butenoic acid (3724-65-0) + (R)-3-(2-Methyl-propane-2-sulfinyl)-butyric acid (141079-96-1, 141079-97-2)

Conditions	Yield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h; Yield given;	A 1% B n/a

pyridine (110-86-1) + 3-chloro-2-iodo-butyric acid (857780-67-7) → 2-butenoic acid (3724-65-0) + 2-iodo-crotonic acid

pyridine (110-86-1) + diethyl ether (60-29-7) + malonic acid (141-82-2) + acetaldehyde (75-07-0) → 2-butenoic acid (3724-65-0)

Conditions	Yield
anfangs in Eiswasser, dann bei Zimmertemperatur;

pyridine (110-86-1) + diethyl ether (60-29-7) + malonic acid (141-82-2) + acetaldehyde (75-07-0) → 2-butenoic acid (3724-65-0) + 3-Hydroxybutyric acid (300-85-6, 625-71-8)

Conditions	Yield
anfangs in Eiswasser, dann bei Zimmertemperatur;

pyridine (110-86-1) + ethanol (64-17-5) + malonic acid (141-82-2) + acetaldehyde (75-07-0) → 2-butenoic acid (3724-65-0)

carbon disulfide (75-15-0) + (Z)-but-2-enoic acid (503-64-0) → 2-butenoic acid (3724-65-0)

Conditions	Yield
Sonnenlicht;

tetrachloromethane (56-23-5) + but-3-enoic acid (625-38-7) → 2-butenoic acid (3724-65-0)

Conditions	Yield
Geschwindigkeit;
at 100℃; Geschwindigkeit;
at 150℃; Geschwindigkeit;

tetrachloromethane (56-23-5) + 3-fluorobutyric acid (2105-80-8) → 2-butenoic acid (3724-65-0)

but-3-enoic acid (625-38-7) + furan-2,3,5(4H)-trione pyridine (1:1) → 2-butenoic acid (3724-65-0)

but-3-enoic acid (625-38-7) + furan-2,3,5(4H)-trione pyridine (1:1) → 2-butenoic acid (3724-65-0) + 3-Hydroxybutyric acid (300-85-6, 625-71-8)

but-3-enoic acid (625-38-7) → 2-butenoic acid (3724-65-0)

Conditions	Yield
beim Kochen;

3-ethoxybutanoic acid (19878-71-8) → 2-butenoic acid (3724-65-0) + ethanol (64-17-5)

Conditions	Yield
bei der Destillation;

(Z)-but-2-enoic acid (503-64-0) → 2-butenoic acid (3724-65-0)

2-butenoic acid (3724-65-0) → butyric acid (107-92-6)

Conditions	Yield
With potassium hydroxide; hydrogen; [RhCl(Ph3P)2]; Ph2PO2CCH=CMe2 In acetone at 22℃; under 2280 Torr; for 17h;	100%
With sodium tetrahydroborate; sodium hydroxide In water at 20 - 60℃;	90%
With sodium hydroxide; hydrogen; nickel In water hydrogen generated in situ electrochemically on Raney nickel electrode;	60%

2-butenoic acid (3724-65-0) → crotonic anhydride (623-68-7)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;	100%
With isocyanate de chlorosulfonyle; triethylamine In dichloromethane for 7h; Ambient temperature;	86%
With N,N,N',N'-tetramethylchlorformamidinium chloride; triethylamine In dichloromethane at -30 - 20℃; for 18h;	83%

piperidine (110-89-4) + 2-butenoic acid (3724-65-0) → 1-crotonoylpiperidine (50838-22-7)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20 - 25℃; for 1h;	100%
Yield given. Multistep reaction;

2-butenoic acid (3724-65-0) + benzylamine (100-46-9) → N-benzyl-3-methylpropenamide (51944-67-3)

Conditions	Yield
With silica gel at 130℃; for 1.33333h; Microwave irradiation; Green chemistry;	100%
Stage #1: 2-butenoic acid With 4-methyl-morpholine In tetrahydrofuran for 3h; Stage #2: benzylamine With 4-methyl-morpholine In tetrahydrofuran for 3h; Further stages.;	86%
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.0833333h;	79%
Yield given. Multistep reaction;

2-butenoic acid (3724-65-0) → D,L-3-azidobutyric acid (138051-81-7)

Conditions	Yield
With trimethylsilylazide In neat (no solvent) at 60℃; for 12h;	99%

2-butenoic acid (3724-65-0) + acrylic acid (79-10-7) + zinc(II) oxide → zinc acrylate-crotonate

Conditions	Yield
In water	98.7%

2-butenoic acid (3724-65-0) → 3-bromobutyric acid (2623-86-1)

Conditions	Yield
With hydrogen bromide In diethyl ether at 0℃; for 16h; Inert atmosphere;	98%
With hydrogen bromide; acetic acid at 20℃; for 2h;	93%

2-butenoic acid (3724-65-0) + N-p-toluenesulfonylpyrrole (17639-64-4) → 4-methyl-1-tosyl-4,5-dihydrocyclopenta[b]pyrrol-6-one (1536277-53-8)

Conditions	Yield
With {[Zn4(pdpa)2(H2O)8]*H2O}n; trifluoroacetic anhydride In 1,2-dichloro-ethane for 4h; Reagent/catalyst; Nazarov Cyclization; Reflux;	98%
With C10H2N16(4-)*3H2O*4Ag(1+); trifluoroacetic anhydride In 1,2-dichloro-ethane for 5h; Reagent/catalyst; Nazarov Cyclization; Reflux;	91%
With iron(III) chloride; trifluoroacetic anhydride In dichloromethane for 4h; Reflux;	53%

2-butenoic acid (3724-65-0) + benzylamine (100-46-9) → (2E)-N-benzylbut-2-enamide (89232-30-4)

Conditions	Yield
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;	98%

2-butenoic acid (3724-65-0) + thiophenol (108-98-5) → 2-hydroxycarbonyl-1-methylethyl phenyl sulfide (880-13-7)

Conditions	Yield
With tetrabutyl ammonium fluoride at 50℃; for 2h;	97%
With iodine at 20℃; for 12h;	86%
With iodine at 20℃; for 12h;	86%
With triethylamine

2-butenoic acid (3724-65-0) + 3-(trimethylsilyl)-2-oxazolidinone (43112-38-5) → dimethylenecyclourethane (497-25-6) + (crotonoyloxy)trimethylsilane (88239-44-5, 18269-64-2)

Conditions	Yield
trifluorormethanesulfonic acid at 15℃; for 0.0333333h;	A n/a B 97%

2-butenoic acid (3724-65-0) + 10,10'-oxybisphenarsazine (4095-45-8) → 5,10-Dihydrophenarsazin-10-crotonat (25094-66-0)

Conditions	Yield
In toluene Heating;	96.6%

2-butenoic acid (3724-65-0) + (4RS)-1-pentadecen-4-ol (76828-23-4) → (4RS)-4-(2-butenoyloxy)-1-pentadecene

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h; Acylation; Heating; 1 h;	96%

2-butenoic acid (3724-65-0) + (R)-4-Hydroxypentadec-1-ene (76828-23-4, 125946-61-4, 125946-59-0) → (4R)-4-(2-butenoyloxy)-1-pentadecene

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h; Acylation; Heating; 1 h;	96%

2-butenoic acid (3724-65-0) + S,S-diethyl dithiocarbonate (623-80-3) → 3-ethylthio acid (89534-40-7)

Conditions	Yield
With potassium hydroxide at 90℃; for 2h;	95%

2-butenoic acid (3724-65-0) + aniline (62-53-3) → crotonanilide (1733-40-0)

Conditions	Yield
With triethylamine; betamethasone sodium phosphate In N,N-dimethyl-formamide for 0.333333h; Ambient temperature;	95%
With zeolite-HY In neat (no solvent) for 0.916667h; Irradiation;	80%
With isocyanate de chlorosulfonyle; triethylamine In dichloromethane 1.) 0 - 10 deg C, 3 h, 2.) room temp., 5 h;	68%
Yield given. Multistep reaction;

2-butenoic acid (3724-65-0) + benzene (71-43-2) → 3-methylindanone (6072-57-7)

Conditions	Yield
With aluminum (III) chloride at 80℃; for 4h; Inert atmosphere;	95%
With aluminium trichloride for 4h; Heating;	82%
With aluminum (III) chloride for 5h; Friedel-Crafts Acylation; Reflux;	81%
With aluminium trichloride
With aluminum (III) chloride Inert atmosphere;

2-butenoic acid (3724-65-0) + buta-1,3-diene (106-99-0) → 2,7-octadienyl crotonate

Conditions	Yield
With triphenylphosphine; palladium(II) acetylacetonate; triethylaluminum In tetrahydrofuran at 60℃; for 6h;	95%

2-butenoic acid (3724-65-0) + methyl diazoacetate (6832-16-2) → (E)-But-2-enoic acid methoxycarbonylmethyl ester

Conditions	Yield
With Cu(II)-Mont K 10 clay In dichloromethane at 25℃; for 5h; Condensation;	95%

2-butenoic acid (3724-65-0) → 3-mercaptobutyric acid (26473-49-4)

Conditions	Yield
With hydrogen sulfide; C8H20N2O*C2HF6NO4S2 at 90℃; for 12h;	95%
With hydrogen sulfide; molecular sieves 4A (powder) In 1-methyl-pyrrolidin-2-one at 100℃; under 3000.3 - 5850.59 Torr; for 5h; Product distribution / selectivity;	72 - 82 %Chromat.
With hydrogen sulfide; molecular sieves 4A (beads) In 1-methyl-pyrrolidin-2-one at 100℃; under 3225.32 - 4125.41 Torr; for 5h; Product distribution / selectivity;	72 %Chromat.

2-butenoic acid (3724-65-0) + 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine (733039-20-8) → 2-chloro-5-methyl-8-cyclopentylpyridin[2,3-d]pyrimidin-8-hydro-7-one (1013916-37-4)

Conditions	Yield
With triethylamine; palladium dichloride In 1-methyl-pyrrolidin-2-one at 20 - 75℃; for 6h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;	94.8%
Stage #1: 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With triethylamine; palladium dichloride In tetrahydrofuran at 60℃; for 5h; Stage #2: 2-butenoic acid In tetrahydrofuran for 2h; Temperature; Reagent/catalyst; Solvent;	89.08%
Stage #1: 2-butenoic acid; 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; palladium dichloride In water; N,N-dimethyl-formamide at 85℃; for 8h; Inert atmosphere; Stage #2: With acetic anhydride In water; N,N-dimethyl-formamide for 2h; Inert atmosphere;	85.2%
Stage #1: 2-butenoic acid; 5-bromo-2-chloro-N-cyclopentylaminopyrimidine-4-amine With bis(benzonitrile)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In tetrahydrofuran at 75℃; for 20h; Heck Reaction; Inert atmosphere; Stage #2: In acetic anhydride at 75℃; for 2h; Temperature; Reagent/catalyst; Solvent;	80%
With triethylamine; palladium dichloride In 1-methyl-pyrrolidin-2-one at 75℃; for 6h; Temperature; Inert atmosphere;

2-butenoic acid (3724-65-0) + desmethyl anethole trithione (18274-81-2) → 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl but-2-enoate

Conditions	Yield
Stage #1: 2-butenoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: desmethyl anethole trithione In dichloromethane at 25℃;	94.4%

2-butenoic acid (3724-65-0) + anthracene (120-12-7) → trans-9,10-dihydro-12-methyl-11,12-ethanoanthracene-11-carboxylic acid (7152-29-6, 77154-95-1, 77155-01-2)

Conditions	Yield
at 140℃; for 60h;	94%
at 150 - 200℃; for 6h; autoclave;

2-butenoic acid (3724-65-0) + dithiocarbonic acid S,S'-dibenzyl ester (26504-28-9) → 3-(benzylthio)butanoic acid (23909-09-3)

Conditions	Yield
With potassium hydroxide at 90℃; for 3h;	94%

2-butenoic acid (3724-65-0) → crotonaldehyde (123-73-9)

Conditions	Yield
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h;	94%

2-butenoic acid (3724-65-0) + 4-Fluorothiophenol (371-42-6) → C10H11FO2S

Conditions	Yield
With iodine at 20℃; for 12h;	94%
With iodine at 20℃; for 12h;	94%

2-butenoic acid (3724-65-0) → crotonyl chloride (10487-71-5)

Conditions	Yield
With thionyl chloride at 80℃; for 3h;	93%
With thionyl chloride In Petroleum ether for 4h; Heating;	76%
With Amberlite IRA 93 (PCl5 form) In dichloromethane for 6h; Heating;	51%

2-butenoic acid (3724-65-0) + 1,2-diamino-benzene (95-54-5) → 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (3967-01-9)

Conditions	Yield
With Imidazole hydrochloride In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 0.5h; Schlenk technique;	93%
With aluminum oxide for 0.0111111h; microwave irradiation;	92%
at 150℃; for 7h;	44.2%

2-butenoic acid (3724-65-0) + 3-(trimethylsilyl)-2-oxazolidinone (43112-38-5) → (crotonoyloxy)trimethylsilane (88239-44-5, 18269-64-2)

Conditions	Yield
In tetrachloromethane at 77℃; for 0.25h;	93%
With triethylamine In dichloromethane for 0.5h; Ambient temperature;

Upstream product

• 110-86-1 pyridine 
• 857780-67-7 3-chloro-2-iodo-butyric acid 
• 60-29-7 diethyl ether 
• 141-82-2 malonic acid 
• 75-07-0 acetaldehyde 
• 64-17-5 ethanol 
• 75-15-0 carbon disulfide 
• 503-64-0 (Z)-but-2-enoic acid 
• 56-23-5 tetrachloromethane 
• 625-38-7 but-3-enoic acid 
• 2105-80-8 3-fluorobutyric acid 
• 19878-71-8 3-ethoxybutanoic acid 
• 591-63-9 trans-crotonic acid butyl ester 
• 23153-18-6 1,1,1-Trichloro-3-bromobutane 

Downstream Products

• 623-43-8 crotonic acid methyl ester 
• 10024-70-1 3-methoxybutanoic acid 
• 123-73-9 crotonaldehyde 
• 3234-54-6 vinyl crotonate 
• 16630-65-2 S-methyl-3-mercaptobutyric acid 
• 623-70-1 ethyl (E)-crotonate 
• 73545-17-2 trans-crotonic acid isopentyl ester 
• 56172-46-4 trans-crotonic acid-(3,7-dimethyl-octa-2,6-dienyl ester) 
• 73545-15-0 isobutyl trans-crotonate 
• 7465-34-1 2-(1,2-dimethyl-propyl)-N-phenyl-malonamic acid 
• 188290-36-0 thiophene 
• 108-31-6 maleic anhydride 
• 110-16-7 maleic acid 
• 104-90-5 5-ethyl-2-methyl-pyridine 

Relevant articles and documents

Role of peroxy compounds in oxidation of crotonaldehyde with molecular oxygen

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The invention discloses a method for synthesizing muscone by utilizing beta-monomethyl methylglutarate. According to the method, beta-monomethyl methylglutarate and alpha,omega-dodecanedioic acid monomethyl ester respectively prepared through a heteropoly acid catalytic transesterification method are used as raw materials, and Kolbe electrolysis, acyloin condensation and reduction reaction are performed to prepare the muscone. The method of the present invention has advantages of high raw material utilization rate, mold condition, easy control and environmental protection, and is suitable for industrial production .

Enantioselective Palladium-Catalyzed Oxidative Cascade Cyclization of Aliphatic Alkenyl Amides

The catalyst system of Pd(TFA)2/(S,S)-diPh-pyrox is reported to promote the highly efficient enantioselective oxidative cascade cyclization of alkene-tethered aliphatic acrylamides under mild aerobic conditions. A series of pyrrolizidine derivatives have been synthesized in good yield and excellent enantioselectivity. Deuterium-labeling experiments have revealed that the reaction proceeded through an anti-aminopalladation (anti-AP) pathway with high selectivity. The transition states for the anti-AP step have been calculated to account for the observed enantioselectivity.