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4180-23-8

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4180-23-8 Usage

Description

(E)-Anethol is a phenylpropanoid that has been found in P. anisum seed oil and has antifungal and antioxidant activity. It is active against fermentatively growing S. cerevisiae under hypoxic, but not normoxic, conditions (MIC = 100 μg/ml), and against C. parapsilosis when used at a concentration of 15% w/w. (E)-Anethol has antioxidant activity in a Trolox equivalent antioxidant capacity (TEAC) assay but does not scavenge 2,2-diphenyl-1-picrylhydrazel (DPPH) radicals in a cell-free assay.

Chemical Properties

trans-anethole is a clear colorless to pale yellow liquid and has a characteristic anise, sweet, spicy, warm odor and corresponding sweet taste. Anethole (1-methoxy-4-propenyl-benzene, isoestragole) is an alkoxypropenylbenzene derivative and an important favoring component of essential oils of more than 20 plant species. Essential oils from seeds of anise (Pimpinellaanisum L.), star anise (Illicium verum Hook.f), and sweet fennel (Foeniculum vulgare Mill. var. dulce) are the main sources used for the isolation of anethole. Two isomers of anethole occur in nature: E- or trans-anethole and Z-or cis-anethole. About 90 % of natural anethole is trans-isomer. Besides separation from natural essential oils, anethole is obtained using the rectification of crude sulfate turpentine and/or the organic synthesis starting from methylchavicol or anisole and propionic anhydride. Compared to natural compound, synthetic trans-anethole is impurified with higher amounts of cis-isomer.

Occurrence

Anethole is methyl ether of oestrone and has been found in fennel, aniseed, coriander, and many other volatile oils.

Uses

Different sources of media describe the Uses of 4180-23-8 differently. You can refer to the following data:
1. flavoring agent in food, dentifrices, etc.; in perfumery for soap, etc.; in pharmaceuticals as flavor; in photography and in embedding materials in microscopy; some perfumery uses (fennei; absinthe; Hyacinth jacinthe; detergents; magnolia). Natural occurrence: star anise
2. platelet aggregation inhibitor
3. trans-Anethole is used to inhibits lung and forestomach carcinogenesis, used as carbon and energy supplement in the culture media of Pseudomonas putida strain. It is also used as used as a flavoring substance.

Preparation

Different sources of media describe the Preparation of 4180-23-8 differently. You can refer to the following data:
1. By esterification of p-cresol with methyl alcohol and with subsequent condensation with α-cetaldehyde (Perknis); the most common method of preparation is from pine oil. By fractional distillation of the essential oils of anise, star anise, and fennel; the anise essences contain an average of 85% anethole; fennel, from 60 to 70%.
2. By isomerization of estragole using alcoholic potassium hydroxide as agent (Arctander, 1969).

Taste threshold values

Taste characteristics at 10 ppm: sweet, anise, licorice and spicy with a lingering, sweet aftertaste.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1797, 1985 DOI: 10.1021/jo00211a002Tetrahedron, 24, p. 2183, 1968 DOI: 10.1016/0040-4020(68)88120-7

General Description

trans-Anethole is a naturally occuring flavouring agent. It has insecticidal, larvicidal, and antimicrobial properties.

Biochem/physiol Actions

Naturally occurring phenylpropene derivative that is estrogenic at lower concentrations and cytotoxic at higher concentrations to cancer cell lines. The cytotoxicity is related to the metabolism of trans-anethole to 4-hydroxy-1-propenylbenzene.

Anticancer Research

It is one of the major constituents of essential oil of fennel and anise and belongs tothe class of phenylpropenes. It has the capacity to block both inflammation andcarcinogenesis. It is an antioxidant and also a suppressor of NF-κB activation byIκBα degradation (Aggarwal and Shishodia 2004).

Metabolism

Anethole is metabolized by oxidation of the propenyl group and is excreted as anisic acid (Williams, 1959). The metabolism of trans-anethole used in the preparation of anis-flavoured alcoholic beverages was studied in the rabbit and rat after iv and oral administration. It was excreted rapidly from the animal regardless of the method of administration. After iv injection it was found concentrated in the liver, lungs and brain; after oral administration, absorption was slight and most of it remained in the stomach. Ethyl alcohol has no effect on the metabolism (Le Bourhis, 1968).

Check Digit Verification of cas no

The CAS Registry Mumber 4180-23-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,8 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4180-23:
(6*4)+(5*1)+(4*8)+(3*0)+(2*2)+(1*3)=68
68 % 10 = 8
So 4180-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+

4180-23-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P0494)  trans-Anethole  >98.0%(GC)

  • 4180-23-8

  • 25g

  • 135.00CNY

  • Detail
  • TCI America

  • (P0494)  trans-Anethole  >98.0%(GC)

  • 4180-23-8

  • 100g

  • 390.00CNY

  • Detail
  • TCI America

  • (P0494)  trans-Anethole  >98.0%(GC)

  • 4180-23-8

  • 500g

  • 865.00CNY

  • Detail
  • Alfa Aesar

  • (A13482)  trans-Anethole, 98+%, stab.   

  • 4180-23-8

  • 25g

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A13482)  trans-Anethole, 98+%, stab.   

  • 4180-23-8

  • 100g

  • 568.0CNY

  • Detail
  • Alfa Aesar

  • (A13482)  trans-Anethole, 98+%, stab.   

  • 4180-23-8

  • 500g

  • 1356.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1218)    pharmaceutical secondary standard; traceable to USP

  • 4180-23-8

  • PHR1218-2.2ML

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (10368)  trans-Anethole  analytical standard

  • 4180-23-8

  • 10368-1ML

  • 354.51CNY

  • Detail
  • Sigma-Aldrich

  • (10368)  trans-Anethole  analytical standard

  • 4180-23-8

  • 10368-5ML

  • 1,409.85CNY

  • Detail
  • USP

  • (1035005)  Anethole  United States Pharmacopeia (USP) Reference Standard

  • 4180-23-8

  • 1035005-4X0.5ML

  • 4,647.24CNY

  • Detail

4180-23-8Synthetic route

Estragole
140-67-0

Estragole

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With Polystyrene-supported 4-tert-butyl-2-(diisopropylphosphino)-1H-imidazole and ruthenium complex In [(2)H6]acetone at 25℃; for 0.166667h; Reagent/catalyst; Inert atmosphere; Glovebox; stereoselective reaction;99%
With PdClMe(2,9-dimethyl-1,10-phenanthroline); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In chloroform-d1 at 0℃; for 16h; Sealed tube;99%
With nickel(II) iodide; 6,6'-dimethyl-2,2'-bipyridine; phosphonic acid diethyl ester; zinc In N,N-dimethyl acetamide at 35℃; for 24h;97%
cis-Anethole
25679-28-1

cis-Anethole

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
Stage #1: cis-Anethole With cobalt(II) chloride; 2,2'-bis(diphenylphosphino)diphenylamine In toluene at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: With sodium triethylborohydride In toluene at 20℃; for 1h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; diastereoselective reaction;
99%
With sodium hydrogen sulfate at 100 - 155℃; for 1h; Temperature;95.4%
cadmium(II) sulphide In dichloromethane Product distribution; Irradiation;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

potassium trifluoro(prop-1-en-2-yl)borate

potassium trifluoro(prop-1-en-2-yl)borate

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With potassium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In water; isopropyl alcohol at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;97%
para-iodoanisole
696-62-8

para-iodoanisole

(E)-phenyl(prop-1-en-1-yl)silane

(E)-phenyl(prop-1-en-1-yl)silane

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
Stage #1: (E)-phenyl(prop-1-en-1-yl)silane With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.05h; Glovebox; Inert atmosphere; Schlenk technique;
Stage #2: para-iodoanisole With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran for 10h; Hiyama Coupling; Glovebox; Inert atmosphere; Schlenk technique;
97%
ethyltriphenylphosphonium bromide
1530-32-1

ethyltriphenylphosphonium bromide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
Stage #1: ethyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -78 - 25℃; for 3.83333h; Wittig reaction; Inert atmosphere;
Stage #3: With dichloro bis(acetonitrile) palladium(II) In chloroform at 25℃; for 72h;
94%
1-phenyl-2-(2-pyridyl)-1,2-disodiumethane

1-phenyl-2-(2-pyridyl)-1,2-disodiumethane

1-(1,2-dibromopropyl)-4-methoxybenzene
1201-60-1

1-(1,2-dibromopropyl)-4-methoxybenzene

A

2-(1,2,2-triphenylvinyl)pyridine

2-(1,2,2-triphenylvinyl)pyridine

B

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.166667h;A n/a
B 91%
anethole
104-46-1

anethole

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II) In dichloromethane at 20℃; for 14h;90%
1-(1,2-dibromopropyl)-4-methoxybenzene
1201-60-1

1-(1,2-dibromopropyl)-4-methoxybenzene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With 1-phenyl-2-(2-pyridyl)-1,2-disodiumethane In tetrahydrofuran at 0℃; for 10h;90%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-(2-fluorovinyl)-4-methoxybenzene
15197-86-1

1-(2-fluorovinyl)-4-methoxybenzene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;89%
1-(4-methoxyphenyl)-1-propanol
5349-60-0

1-(4-methoxyphenyl)-1-propanol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With 1-hexyl-3-methyl-1-imidazolium bromide at 140℃; for 0.116667h; Reactivity; Reagent/catalyst; Time; Microwave irradiation; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;87%
With silica gel In 1,4-dioxane for 0.05h; microwave irradiation;67%
With trichlorophosphate In pyridine for 2h; Heating;
(E)-p-methoxy-cinnamyl alcohol
53484-50-7

(E)-p-methoxy-cinnamyl alcohol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With bis(tricyclohexylphosphine)nickel(II) dichloride; n-hexylmagnesium chloride; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique;86%
1-(4-methoxyphenyl)prop-1-yl acetate
16031-55-3

1-(4-methoxyphenyl)prop-1-yl acetate

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With 1-hexyl-3-methyl-1-imidazolium bromide at 140℃; for 0.166667h; Microwave irradiation; chemoselective reaction;82%
para-iodoanisole
696-62-8

para-iodoanisole

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With orotic acid; caesium carbonate In acetone at 100℃; for 24h; Suzuki coupling; Inert atmosphere;82%
(1RS,2RS)-1-(4'-methoxyphenyl)-2-(diphenylphosphinoyl)propan-1-ol
88533-70-4, 88533-77-1, 103785-85-9, 103785-86-0

(1RS,2RS)-1-(4'-methoxyphenyl)-2-(diphenylphosphinoyl)propan-1-ol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide81.3%
2-(Diphenyl-phosphinoyl)-1-(4-methoxy-phenyl)-propan-1-ol
88533-70-4, 88533-77-1, 103785-85-9, 103785-86-0

2-(Diphenyl-phosphinoyl)-1-(4-methoxy-phenyl)-propan-1-ol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide81%
C17H18O3
1106676-03-2

C17H18O3

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With 1-hexyl-3-methyl-1-imidazolium bromide at 140℃; for 0.166667h; Microwave irradiation; chemoselective reaction;80%
1,1-bis(4-methoxyphenyl)propane
4792-39-6

1,1-bis(4-methoxyphenyl)propane

A

methoxybenzene
100-66-3

methoxybenzene

B

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With silica gel In water at 400℃; Inert atmosphere;A 77.3%
B 45.1%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

propionaldehyde
123-38-6

propionaldehyde

malononitrile
109-77-3

malononitrile

A

3-amino-4'-methoxy-6-methyl-[1,1'-biphenyl]-2,4-dicarbonitrile
1338442-76-4

3-amino-4'-methoxy-6-methyl-[1,1'-biphenyl]-2,4-dicarbonitrile

B

2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile
55525-92-3

2-amino-4-ethyl-5-methylbenzene-1,3-dicarbonitrile

C

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With morpholine In N,N-dimethyl-formamide at 80℃;A 77%
B 8%
C 10%
(1R*,2S*)-2-Diphenylphosphinoyl-1-(4-methoxyphenyl)propan-1-ol
88533-70-4, 88533-77-1, 103785-85-9, 103785-86-0

(1R*,2S*)-2-Diphenylphosphinoyl-1-(4-methoxyphenyl)propan-1-ol

A

cis-Anethole
25679-28-1

cis-Anethole

B

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxideA 75%
B 6%
1-(4-methoxylphenyl)-2-propen-1-ol
51410-44-7

1-(4-methoxylphenyl)-2-propen-1-ol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With bis(tricyclohexylphosphine)nickel(II) dichloride; n-hexylmagnesium chloride; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique;75%
ethyl phenyl sulfone
599-70-2

ethyl phenyl sulfone

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With C24H20ClN2OPRu; potassium tert-butylate In 1,4-dioxane at 125℃; for 5h; Inert atmosphere; Schlenk technique; Glovebox;71%
4-Methoxypropiophenone
121-97-1

4-Methoxypropiophenone

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium carbonate; bis(pinacol)diborane; bis[2-(diphenylphosphino)phenyl] ether In hexane at 70℃; for 10h; Glovebox; Sealed tube; Inert atmosphere; stereoselective reaction;68%
Estragole
140-67-0

Estragole

carbon monoxide
201230-82-2

carbon monoxide

A

4-n-propylanisole
104-45-0

4-n-propylanisole

B

3-(p-methoxyphenyl)-2-methylpropionaldehyde
5462-06-6

3-(p-methoxyphenyl)-2-methylpropionaldehyde

C

4-(4-methoxyphenyl)butyraldehyde
56047-51-9

4-(4-methoxyphenyl)butyraldehyde

D

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With hydrogen; N-dodecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide; {Rh(cod)[μ-S(CH2)3Si(OMe)3]}2; triphenylphosphine In water; butan-1-ol at 80℃; under 10350.8 Torr; for 6h; microemulsion/sol-gel; Further byproducts given;A 1.4%
B 27.4%
C 63.8%
D 6.7%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

(E)-propenyl-tri-n-butylstannane
105494-65-3, 66680-85-1, 66680-84-0

(E)-propenyl-tri-n-butylstannane

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With palladium diacetate; orotic acid; cesium fluoride In 1,4-dioxane at 100℃; for 18h; Stille Cross Coupling; Sealed tube; Inert atmosphere; Schlenk technique;62%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

allyltributylstanane
24850-33-7

allyltributylstanane

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; lithium chloride In diethylene glycol dimethyl ether at 130℃; Stille Cross Coupling; Inert atmosphere; regioselective reaction;62%
trans-1-methoxy-4-(2-methylsulfanylvinyl)benzene
14846-66-3

trans-1-methoxy-4-(2-methylsulfanylvinyl)benzene

methylmagnesium bromide
75-16-1

methylmagnesium bromide

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
bis(triphenylphosphine)nickel(II) chloride In diethyl ether; benzene Heating;60%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

A

acetone
67-64-1

acetone

B

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With iron(III) chloride; silver tetrafluoroborate In dichloromethane at 25℃; for 3h; Inert atmosphere;A n/a
B 60%
cyclopropyl bromide
4333-56-6

cyclopropyl bromide

3-(4-methoxyphenyl)-1-iodopropane
113379-13-8

3-(4-methoxyphenyl)-1-iodopropane

A

1-(3-cyclopropylpropyl)-4-methoxybenzene

1-(3-cyclopropylpropyl)-4-methoxybenzene

B

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
Stage #1: cyclopropyl bromide With iodine; magnesium In 2-methyltetrahydrofuran for 1.5h; Inert atmosphere; Reflux;
Stage #2: 3-(4-methoxyphenyl)-1-iodopropane With N,N,N,N,-tetramethylethylenediamine; cobalt(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 1h; Catalytic behavior; Temperature; Inert atmosphere; chemoselective reaction;
A 56%
B 17%
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

2-Bromo-1-(4-methoxy-phenyl)-propan-1-ol
82947-15-7, 82947-17-9

2-Bromo-1-(4-methoxy-phenyl)-propan-1-ol

Conditions
ConditionsYield
With hypobromous acid In 1,4-dioxane at 20℃; for 0.5h;100%
acetic acid
64-19-7

acetic acid

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

C12H15BrO3

C12H15BrO3

Conditions
ConditionsYield
With N-Bromosuccinimide; benzamidin for 3h;100%
pyridin-2-yl sulfenyl chloride
59089-57-5

pyridin-2-yl sulfenyl chloride

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

trans-3-(4-methoxyphenyl)-2-methyl-2H,3H-thiazolo[3,2-]pyridin-4-ium chloride

trans-3-(4-methoxyphenyl)-2-methyl-2H,3H-thiazolo[3,2-]pyridin-4-ium chloride

Conditions
ConditionsYield
Stage #1: pyridin-2-yl sulfenyl chloride With sulfuryl dichloride In dichloromethane at 20℃; for 0.166667h;
Stage #2: E-1-(4'-methoxyphenyl)prop-1-ene In dichloromethane at 20℃; for 20h; regioselective reaction;
100%
2,2'-dipyridyldiselenide
59957-75-4

2,2'-dipyridyldiselenide

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

trans-3-(4-methoxyphenyl)-2-methyl-2H,3H-selenazolo[3,2-]pyridin-4-ium chloride

trans-3-(4-methoxyphenyl)-2-methyl-2H,3H-selenazolo[3,2-]pyridin-4-ium chloride

Conditions
ConditionsYield
Stage #1: 2,2'-dipyridyldiselenide With sulfuryl dichloride In chloroform at 20℃; for 0.333333h;
Stage #2: E-1-(4'-methoxyphenyl)prop-1-ene In chloroform at 20℃; for 5h; Reflux; regioselective reaction;
100%
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

4-n-propylanisole
104-45-0

4-n-propylanisole

Conditions
ConditionsYield
With magnesium; nickel dichloride In water at 20℃; for 12h; Sealed tube; Photolysis; Inert atmosphere;99%
With oxygen; hydrazine hydrate In propan-1-ol at 120℃; under 15001.5 Torr; for 0.5h;91%
With oxygen; hydrazine hydrate In propan-1-ol at 120℃; under 15001.5 Torr; for 0.166667h; Flow reactor;91%
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; acrylic acid methyl ester In dichloromethane for 2h; Reflux; Inert atmosphere;99%
With C33H43Cl2N3O3RuS In toluene at 110℃; for 2h; Inert atmosphere;90%
With silica-supported Hoveyda-Grubbs II catalyst In hexane at 70℃; for 14h; Inert atmosphere; Glovebox;74%
(1,3-dimesitylimidazolin-2-ylidene)(C2H4)RuCl2; (p-cymene)RuCl2 In toluene at 85℃; for 2h;90 % Turnov.
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

trans-2-(p-methoxyphenyl)-3-methyloxirane

trans-2-(p-methoxyphenyl)-3-methyloxirane

Conditions
ConditionsYield
With dihydrogen peroxide; Ru(2,2':6',2''-terpyridine)(2,6-pyridinedicarboxylate) In tert-Amyl alcohol at 20℃; for 12h; Conversion of starting material;99%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

ethyl benzenesulfenate
54815-45-1

ethyl benzenesulfenate

sodium thiocyanide
540-72-7

sodium thiocyanide

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(1R*,2R*)-1-isothiocyanato-1-(4-methoxyphenyl)-2-phenylthiopropane

(1R*,2R*)-1-isothiocyanato-1-(4-methoxyphenyl)-2-phenylthiopropane

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; sodium thiocyanide In chloroform at 20℃; for 1h;
Stage #2: ethyl benzenesulfenate; E-1-(4'-methoxyphenyl)prop-1-ene In chloroform
99%
styrene
292638-84-7

styrene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

1-methoxy-4-((1S*,2R*,4S*)-2-methyl-4-phenylcyclobutyl)benzene

1-methoxy-4-((1S*,2R*,4S*)-2-methyl-4-phenylcyclobutyl)benzene

Conditions
ConditionsYield
With 9-(2-methylphenyl)-1,3,6,8-tetramethoxythioxanthylium trifluoromethanesulfonate In nitromethane at 20℃; for 2h; Catalytic behavior; Solvent; Reagent/catalyst; Irradiation; regioselective reaction;99%
With iron perchlorate hexahydrate In ethyl acetate at 40℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; diastereoselective reaction;88%
With iron perchlorate hexahydrate In ethyl acetate at 40℃; under 760.051 Torr; for 24h; Solvent; Reagent/catalyst;88%
With Fe(3,4,7,8-tetramethyl-1,10-phenanthroline)3(PF6)3 In 2,2,2-trifluoroethanol; 1,2-dichloro-ethane at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent;86%
t-butyl 2-diazobut-3-enoate
132524-91-5

t-butyl 2-diazobut-3-enoate

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

tert-butyl 5-(4-methoxyphenyl)-4-methylcyclopent-1-enecarboxylate

tert-butyl 5-(4-methoxyphenyl)-4-methylcyclopent-1-enecarboxylate

Conditions
ConditionsYield
With tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In nitromethane; dichloromethane at 35℃; for 1h; Reagent/catalyst; Irradiation; diastereoselective reaction;99%
2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(1S,2S)-4'-methoxy-2,4,5-trimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

(1S,2S)-4'-methoxy-2,4,5-trimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions
ConditionsYield
With cross-linked copolymer based on polymethyl methacrylate and 4,7-diphenylbenzothiadiazole; air In nitromethane at 20℃; for 8h; Diels-Alder Cycloaddition; UV-irradiation;99%
With 9-fluorenone In nitromethane at 20℃; for 6h; Catalytic behavior; Mechanism; Reagent/catalyst; Concentration; Solvent; Diels-Alder Cycloaddition; Irradiation;74%
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

isoprene
78-79-5

isoprene

(1S,2S)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

(1S,2S)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions
ConditionsYield
With cross-linked copolymer based on polymethyl methacrylate and 4,7-diphenylbenzothiadiazole; air In nitromethane at 20℃; for 4h; Solvent; Reagent/catalyst; Diels-Alder Cycloaddition; UV-irradiation;99%
With 9-fluorenone In nitromethane at 20℃; for 23h; Diels-Alder Cycloaddition; Irradiation;88%
2,4-Dimethyl-1,3-pentadiene
1000-86-8

2,4-Dimethyl-1,3-pentadiene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

C17H24O

C17H24O

Conditions
ConditionsYield
With cross-linked copolymer based on polymethyl methacrylate and 4,7-diphenylbenzothiadiazole; air In nitromethane at 20℃; for 48h; Diels-Alder Cycloaddition; UV-irradiation;99%
2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(±)-(1S,2S)-4'-methoxy-2,4,5-trimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl
112150-19-3

(±)-(1S,2S)-4'-methoxy-2,4,5-trimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions
ConditionsYield
With tris(2,2’--bipyrazyl)ruthenium(II) bis(tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) In dichloromethane at 20℃; for 1h; Diels-Alder Cycloaddition; Irradiation; regioselective reaction;98%
With iron perchlorate hexahydrate In acetonitrile at 20℃; for 24h; Diels-Alder Cycloaddition; regioselective reaction;98%
With iron(III) chloride In acetonitrile at 20℃; for 1h; Time; Reagent/catalyst; Solvent;98%
4-methoxynaphth-1-ol
84-85-5

4-methoxynaphth-1-ol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan
139016-16-3

(+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan

Conditions
ConditionsYield
With ammonium peroxydisulfate In nitromethane for 12h; Irradiation; Inert atmosphere;98%
With tetrabutylammonium tetrafluoroborate In acetonitrile Electrolysis;96%
With tetrabutylammonium tetrafluoroborate In acetonitrile Electrolysis;96%
With ammonium peroxydisulfate; tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 12h; Irradiation; Schlenk technique;92%
With lithium perchlorate; acetic acid In acetonitrile for 3h; Ambient temperature; electrolysis, platinum electrodes;64%
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

isoprene
78-79-5

isoprene

(1SR,2SR)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl
112150-17-1

(1SR,2SR)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions
ConditionsYield
With tris(2,2’--bipyrazyl)ruthenium(II) bis(tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) In dichloromethane at 20℃; for 1h; Diels-Alder Cycloaddition; Irradiation; regioselective reaction;98%
With lithium perchlorate In nitromethane at 20℃; Concentration; Diels-Alder Cycloaddition; Electrolysis;98%
With iron perchlorate hexahydrate In acetonitrile at 20℃; for 24h; Reagent/catalyst; Diels-Alder Cycloaddition; regioselective reaction;98%
2-carbonyl-3-butenenitrile
60556-87-8

2-carbonyl-3-butenenitrile

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

trans-3,4-dihydro-2-(4-methoxyphenyl)-3-methyl-2H-pyran-6-carbonitrile

trans-3,4-dihydro-2-(4-methoxyphenyl)-3-methyl-2H-pyran-6-carbonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 168h; hetero-Diels-Alder cycloaddition;98%
benzaldehyde
100-52-7

benzaldehyde

4-nitro-aniline
100-01-6

4-nitro-aniline

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

cis-4-(4-methoxyphenyl)-3-methyl-6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline

cis-4-(4-methoxyphenyl)-3-methyl-6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
Stage #1: benzaldehyde; 4-nitro-aniline In acetonitrile at 20℃; for 1h; Povarov reaction;
Stage #2: E-1-(4'-methoxyphenyl)prop-1-ene With copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 24h; Povarov reaction; diastereoselective reaction;
98%
With boron trifluoride diethyl etherate In acetonitrile at 70℃; for 10h; imino Diels-Alder reaction;95%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

bromocatecholborane
51901-85-0

bromocatecholborane

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(Z)-2-(1-(4-methoxyphenyl)prop-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1217435-96-5

(Z)-2-(1-(4-methoxyphenyl)prop-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: bromocatecholborane With N-Methyldicyclohexylamine; [(bis(3,5-di-tert-butylphenyl)(tert-butyl)phosphine)PdI2]2 In toluene at 70℃; for 0.0833333h; Heck Reaction; Schlenk technique; Inert atmosphere; Sealed tube;
Stage #2: E-1-(4'-methoxyphenyl)prop-1-ene In toluene at 70℃; for 4h; Heck Reaction; Schlenk technique; Sealed tube; Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diol In toluene at 20℃; for 0.5h; stereoselective reaction;
98%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(±)-(5R,6S)-5-(4-methoxyphenyl)-6-methylbicyclo[2.2.1]hept-2-ene

(±)-(5R,6S)-5-(4-methoxyphenyl)-6-methylbicyclo[2.2.1]hept-2-ene

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 20℃; for 2h;98%
para-fluorostyrene
405-99-2

para-fluorostyrene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

1-fluoro-4-((1S*,2S*,3R*)-2-(4-methoxyphenyl)-3-methylcyclobutyl)benzene

1-fluoro-4-((1S*,2S*,3R*)-2-(4-methoxyphenyl)-3-methylcyclobutyl)benzene

Conditions
ConditionsYield
With 9-(2-methylphenyl)-1,3,6,8-tetramethoxythioxanthylium trifluoromethanesulfonate In nitromethane at 20℃; for 2h; Irradiation; regioselective reaction;98%
xanth-9-one
90-47-1

xanth-9-one

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(E)-9-(3-(4-methoxyphenyl)allylidene)-9H-xanthene

(E)-9-(3-(4-methoxyphenyl)allylidene)-9H-xanthene

Conditions
ConditionsYield
With tris(trimethylsilyl)amine; tetramethylammonium fluoride at 60℃; for 5h; Inert atmosphere; Sealed tube; Glovebox;98%
4-methoxy-phenol
150-76-5

4-methoxy-phenol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylbenzofuran
139016-13-0

(+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylbenzofuran

Conditions
ConditionsYield
With ammonium peroxydisulfate In nitromethane for 22h; Catalytic behavior; Solvent; Reagent/catalyst; Irradiation; Inert atmosphere;97%
With ammonium peroxydisulfate; tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 27h; Irradiation; Schlenk technique;88%
With lithium perchlorate; acetic acid In acetonitrile for 2h; Ambient temperature; electrolysis, platinum electrodes;80%
formaldehyd
50-00-0

formaldehyd

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

4-p-methoxyphenyl-5-methyl-1,3-dioxane
5689-72-5

4-p-methoxyphenyl-5-methyl-1,3-dioxane

Conditions
ConditionsYield
resine C35O; hydrogen cation In benzene at 60℃; for 12h;97%
5-(benzyloxy)-[1,1'-biphenyl]-2-ol
1416734-90-1

5-(benzyloxy)-[1,1'-biphenyl]-2-ol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

C29H26O3

C29H26O3

Conditions
ConditionsYield
With ammonium peroxydisulfate; tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 30h; Irradiation; Schlenk technique;97%
4-(benzyloxy)-2-(tert-butyl)phenol
3421-95-2

4-(benzyloxy)-2-(tert-butyl)phenol

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

C27H30O3

C27H30O3

Conditions
ConditionsYield
With ammonium peroxydisulfate; tris(2,2′-bipyrazine-N1,N1′)ruthenium(II) hexafluorophosphate In acetonitrile for 30h; Irradiation; Schlenk technique;97%
7-methyl-3-methene-1,6-octadiene
123-35-3

7-methyl-3-methene-1,6-octadiene

E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

(±)-(1S,2S)-4'-methoxy-2-methyl-4-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-1,1'-biphenyl

(±)-(1S,2S)-4'-methoxy-2-methyl-4-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions
ConditionsYield
With iron perchlorate hexahydrate In acetonitrile at 20℃; for 24h; Diels-Alder Cycloaddition; regioselective reaction;97%
With C26H18N10Ru(2+)*2C32H12BF24(1-) In dichloromethane for 1.5h; Diels-Alder Cycloaddition; Irradiation;88%
With 9-(2-trifluoromethylphenyl)-1,3,6,8-tetramethoxythioxanthylium trifluoromethanesulfonate In nitromethane at 20℃; for 1h; Diels-Alder Cycloaddition; UV-irradiation;84%
With iron(III) chloride In dichloromethane; acetonitrile at 0℃; for 3h;76%

4180-23-8Relevant articles and documents

METHODS OF BORYLATION AND USES THEREOF

-

Page/Page column 61-62, (2021/04/30)

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids

Chen, Kun-Quan,Shen, Jie,Wang, Zhi-Xiang,Chen, Xiang-Yu

, p. 6684 - 6690 (2021/05/31)

Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.

Method for synthesizing 1, 2-disubstituted olefin through reaction of terminal group olefin and sulfoxide

-

Paragraph 0053-0054; 0057-0062; 0074, (2021/02/10)

The invention discloses a method for synthesizing 1, 2-disubstituted olefin by reaction of terminal olefin and sulfoxide. According to the method, terminal olefin with sulfoxide make reaction in one pot in the presence of ferric salt and hydrogen peroxide to generate the 1, 2-disubstituted olefin. sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefin, and a reaction product is 1, 2-disubstituted olefin of which a terminal carbon atom in terminal olefin is coupled with a sulfoxide alkyl group, so that an olefin carbon chain is increased; the reaction conditionsare mild, the selectivity is high, the yield is high, and industrial production is facilitated.

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