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1199-77-5 Usage

Chemical Properties

WHITE TO YELLOWISH CRYSTALS OR CRYSTALLINE POWDER

Uses

Alpha-methylcinnamic acid

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 2520, 1972 DOI: 10.1021/ja00762a060Synthetic Communications, 19, p. 71, 1989 DOI: 10.1080/00397918908050954

Check Digit Verification of cas no

The CAS Registry Mumber 1199-77-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 9 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1199-77:
(6*1)+(5*1)+(4*9)+(3*9)+(2*7)+(1*7)=95
95 % 10 = 5
So 1199-77-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3,(H,11,12)/p-1/b8-7+

1199-77-5 Well-known Company Product Price

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  • TCI America

  • (M1336)  α-Methylcinnamic Acid  >98.0%(GC)(T)

  • 1199-77-5

  • 5g

  • 190.00CNY

  • Detail
  • TCI America

  • (M1336)  α-Methylcinnamic Acid  >98.0%(GC)(T)

  • 1199-77-5

  • 25g

  • 590.00CNY

  • Detail
  • Alfa Aesar

  • (L00806)  alpha-Methylcinnamic acid, 99%   

  • 1199-77-5

  • 5g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (L00806)  alpha-Methylcinnamic acid, 99%   

  • 1199-77-5

  • 25g

  • 600.0CNY

  • Detail
  • Alfa Aesar

  • (L00806)  alpha-Methylcinnamic acid, 99%   

  • 1199-77-5

  • 100g

  • 1849.0CNY

  • Detail

1199-77-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name alpha-Methylcinnamic acid

1.2 Other means of identification

Product number -
Other names α-Methylcinnamic acid

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:1199-77-5 SDS

1199-77-5Synthetic route

C17H16O2
87995-30-0

C17H16O2

toluene
108-88-3

toluene

A

1-methyl-3-(phenylmethyl)-benzene
620-47-3

1-methyl-3-(phenylmethyl)-benzene

B

1-methyl-4-(phenylmethyl)benzene
620-83-7

1-methyl-4-(phenylmethyl)benzene

C

2-benzyltoluene
713-36-0

2-benzyltoluene

D

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;A n/a
B n/a
C n/a
D 98%
methyl 2-methyl-3-phenylacrylate
21370-57-0, 22946-43-6, 25692-59-5

methyl 2-methyl-3-phenylacrylate

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With methanol; potassium hydroxide at 20℃; for 0.5h;95%
With potassium hydroxide In methanol at 20℃; for 0.5h;
2-methyl-3-phenyl-2-propenal
101-39-3

2-methyl-3-phenyl-2-propenal

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 45℃; for 12h; chemoselective reaction;87%
With ethanol; silver(l) oxide
benzaldehyde
100-52-7

benzaldehyde

propionic acid anhydride
123-62-6

propionic acid anhydride

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With potassium carbonate at 140℃;83%
With sodium acetate Perkin reaction; Heating;61.24%
Stage #1: propionic acid anhydride With potassium carbonate at 0℃; for 0.0833333h; Perkin Carboxylic Acid Synthesis;
Stage #2: benzaldehyde at 160 - 180℃; for 12h; Perkin Carboxylic Acid Synthesis;
40%
With sodium proprionate at 180℃;
With sodium acetate at 130 - 135℃;
α-methyl-trans-cinnamaldehyde
15174-47-7

α-methyl-trans-cinnamaldehyde

A

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

B

2-methyl-3-phenylpropionic acid
1009-67-2, 5628-72-8, 14367-54-5, 14367-67-0

2-methyl-3-phenylpropionic acid

Conditions
ConditionsYield
With aldehyde dehydrogenase from E.coli; ene-reductase from Saccharomyces cerevisiae; NADH In aq. phosphate buffer at 30℃; for 1h; pH=7; Time; Enzymatic reaction; chemoselective reaction;A 5%
B 83%
carbon monoxide
201230-82-2

carbon monoxide

(2-bromoprop-1-en-1-yl)benzene
71001-35-9

(2-bromoprop-1-en-1-yl)benzene

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With [bmim]PF6; triethylamine; bis-triphenylphosphine-palladium(II) chloride In water at 100℃; under 15001.2 Torr; for 10h;64%
bromobenzene
108-86-1

bromobenzene

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With potassium carbonate at 80℃; Heck Reaction; Micellar solution;64%
iodobenzene
591-50-4

iodobenzene

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With potassium carbonate at 80℃; Heck Reaction; Micellar solution;62%
1-phenylpropadiene
2327-99-3

1-phenylpropadiene

carbon dioxide
124-38-9

carbon dioxide

A

2-phenyl-3-butenoic acid
30953-25-4

2-phenyl-3-butenoic acid

B

styrylacetic acid
2243-53-0

styrylacetic acid

C

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
Stage #1: 1-phenylpropadiene; carbon dioxide With [Pd(OSO2CF3)(CH3Si(C6H4P(C6H5)2)2)]; diethylzinc In hexane; N,N-dimethyl-formamide at 60℃; for 8h;
Stage #2: With hydrogenchloride In hexane; water; N,N-dimethyl-formamide
A 54%
B 2%
C 7%
methyl 2-iodo-2-methyl-3-phenylpropanoate
91358-54-2

methyl 2-iodo-2-methyl-3-phenylpropanoate

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Heating;48%
With Alkali Product distribution;
2-methyl-3-phenyl-2-propenal
101-39-3

2-methyl-3-phenyl-2-propenal

A

2-methyl-3-phenyl-acrylonitrile
1197-33-7

2-methyl-3-phenyl-acrylonitrile

B

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With nickel(II) sulphate; ammonium hydroxide; sodium hydroxide; dipotassium peroxodisulfate In water for 6h; Ambient temperature;A 21%
B n/a
pyridine
110-86-1

pyridine

benzaldehyde
100-52-7

benzaldehyde

propionic acid
802294-64-0

propionic acid

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 180℃;
benzylidene dichloride
98-87-3

benzylidene dichloride

sodium proprionate
137-40-6

sodium proprionate

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 150℃;
3-hydroxy-2-methyl-3-phenyl-propionic acid
23985-58-2

3-hydroxy-2-methyl-3-phenyl-propionic acid

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With acetic anhydride at 180℃;
With acetyl chloride at 100℃;
3-hydroxy-2-methyl-3-phenyl-propionic acid
23985-58-2

3-hydroxy-2-methyl-3-phenyl-propionic acid

acetic anhydride
108-24-7

acetic anhydride

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 180℃;
sodium proprionate
137-40-6

sodium proprionate

acetic anhydride
108-24-7

acetic anhydride

benzaldehyde
100-52-7

benzaldehyde

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 100℃; im geschlossenen Rohr;
sodium proprionate
137-40-6

sodium proprionate

benzaldehyde
100-52-7

benzaldehyde

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With acetic anhydride at 100℃;
With acetic acid at 200℃;
benzaldehyde
100-52-7

benzaldehyde

propionic acid
802294-64-0

propionic acid

triethylamine
121-44-8

triethylamine

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 180℃;
sodium proprionate
137-40-6

sodium proprionate

benzaldehyde
100-52-7

benzaldehyde

propionic acid anhydride
123-62-6

propionic acid anhydride

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 180℃;
sodium acetate
127-09-3

sodium acetate

benzaldehyde
100-52-7

benzaldehyde

propionic acid anhydride
123-62-6

propionic acid anhydride

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 180℃;
at 150℃;
at 125 - 130℃;
3-hydroxy-2-methyl-3-phenyl-propionic acid
23985-58-2

3-hydroxy-2-methyl-3-phenyl-propionic acid

acetyl chloride
75-36-5

acetyl chloride

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
at 100℃;
methanol
67-56-1

methanol

tetrachloromethane
56-23-5

tetrachloromethane

benzil
134-81-6

benzil

propiononitrile
107-12-0

propiononitrile

A

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

B

benzoic acid
65-85-0

benzoic acid

benzyl chloride
100-44-7

benzyl chloride

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With sodium Multistep reaction;
2-methyl-3-phenylacrylic acid
1895-97-2

2-methyl-3-phenylacrylic acid

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
In benzene Irradiation;
3-methyl-4-phenyl-3-buten-2-one
1901-26-4

3-methyl-4-phenyl-3-buten-2-one

NaOCl

NaOCl

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

acetic acid
64-19-7

acetic acid

acetone
67-64-1

acetone

Ni(CO)4

Ni(CO)4

A

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

B

2-phenyl-buten-(2)-oic acid (1)

2-phenyl-buten-(2)-oic acid (1)

α-methyl-α-benzyliden-acetone

α-methyl-α-benzyliden-acetone

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With sodium hypochlorite
benzaldehyde
100-52-7

benzaldehyde

isosuccinate sodium

isosuccinate sodium

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Conditions
ConditionsYield
With acetic anhydride
benzyl proprionate
122-63-4

benzyl proprionate

A

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

B

α-benzyl-propionic acid benzyl ester

α-benzyl-propionic acid benzyl ester

Conditions
ConditionsYield
With sodium at 130℃;
methanol
67-56-1

methanol

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

methyl 2-methyl-3-phenylacrylate
21370-57-0, 22946-43-6, 25692-59-5

methyl 2-methyl-3-phenylacrylate

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 3h;100%
With hydrogenchloride
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

2-methyl-3-phenylpropanoic acid
1009-67-2

2-methyl-3-phenylpropanoic acid

Conditions
ConditionsYield
Stage #1: α-methylcinnamic acid With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water
99%
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;99%
With hydrogen; potassium hydroxide In water at 20℃; under 760.051 Torr; for 0.5h; Sealed tube;98%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

2-methyl-3-phenylpropionic acid
1009-67-2, 5628-72-8, 14367-54-5, 14367-67-0

2-methyl-3-phenylpropionic acid

Conditions
ConditionsYield
With hydrogen; triethylamine In methanol at 20℃; under 4560.31 Torr; for 0.5h; optical yield given as %ee; enantioselective reaction;99%
With C38H36IrO2P; hydrogen; caesium carbonate In butan-1-ol at 65℃; under 2280.15 Torr; for 6h; enantioselective reaction;99%
With C38H36IrO2P; hydrogen; caesium carbonate In butan-1-ol at 65℃; under 2250.23 Torr; for 6h; Glovebox; enantioselective reaction;99%
With C32H12BF24(1-)*C54H71IrNP(1+); hydrogen; caesium carbonate In methanol at 45℃; under 4560.31 Torr; for 1h; Autoclave; optical yield given as %ee; enantioselective reaction;97%
Multi-step reaction with 2 steps
1: (i) H2SO4, (ii) H2, Pd-C, EtOH
2: α-chymotrypsin, aq. NaOH
View Scheme
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

2-methyl-3-phenylpropionic acid

2-methyl-3-phenylpropionic acid

Conditions
ConditionsYield
With hydrogen; triethylamine; C32H12BF24(1-)*C63H74IrNOP(1+) In methanol under 4500.45 Torr; Product distribution / selectivity; Sealed tube;99%
With C43H36O6P2Rh; hydrogen In methanol under 7600.51 Torr; for 12h; Inert atmosphere;99%
With hydrogen; C43H36O6P2Ru In methanol at 20℃; under 7600.51 Torr; for 12h; enantioselective reaction;99%
With hydrogen; (S)-1-di(3,5-dimethyl-4-methoxyphenyl)phosphino-2-[α-(S)-hydroxy(o-diphenylphosphinophenyl)methyl]ferrocene; [Rh(norbornadiene)2]BF4 In methanol at 25℃; under 3750.38 Torr; for 19h; Product distribution / selectivity;n/a
With hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; [(R(C),R(C)),(S(Fc),S(Fc)),(S(P),S(P))]-1-[2-(1-N,N-dimethylamino-ethyl)-1-ferrocenyl]phenylphosphino-1'-[2-(1-N,N-dimethylaminoethyl)-1-ferrocenyl][4-(trifluoromethyl)phenyl]phosphinoferrocene In methanol at 25℃; under 2250.23 Torr; for 2h; Product distribution / selectivity;
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

3-(tert-butoxycarbonyloxy)-3,4-dihydrobenzotriazine-4-one
442516-54-3

3-(tert-butoxycarbonyloxy)-3,4-dihydrobenzotriazine-4-one

3-hydroxy-3,4-dihydrobenzotriazin-4-onyl α-methylcinnamate
442516-55-4

3-hydroxy-3,4-dihydrobenzotriazin-4-onyl α-methylcinnamate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 1.5h;98%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

N-butylamine
109-73-9

N-butylamine

C14H19NO

C14H19NO

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;95%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

(C6H5)2PO2CC(CH3)CH(C6H5)
111507-06-3

(C6H5)2PO2CC(CH3)CH(C6H5)

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -20℃;94%
2-methyl-2-butylchloride
594-36-5

2-methyl-2-butylchloride

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

C15H20O2

C15H20O2

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 0 - 5℃; Reagent/catalyst; Friedel-Crafts Alkylation;94%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

1-(buta-2,3-dien-1-yl)naphthalene

1-(buta-2,3-dien-1-yl)naphthalene

(E)-3,5-dimethyl-5-(2-(naphthalen-1-yl)vinyl)-4-phenylfuran-2(5H)-one

(E)-3,5-dimethyl-5-(2-(naphthalen-1-yl)vinyl)-4-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;93%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

penta-2,3-dien-1-ylbenzene
13633-08-4

penta-2,3-dien-1-ylbenzene

(E)-5-ethyl-3-methyl-4-phenyl-5-styrylfuran-2(5H)-one

(E)-5-ethyl-3-methyl-4-phenyl-5-styrylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;93%
ethanol
64-17-5

ethanol

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

ethyl (E)-2-methyl-3-phenyl-2-propenoate
7042-33-3

ethyl (E)-2-methyl-3-phenyl-2-propenoate

Conditions
ConditionsYield
With sulfuric acid for 6h; Reflux; Inert atmosphere;92%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

buta-2,3-dienyl-benzene
40339-20-6

buta-2,3-dienyl-benzene

(E)-3,5-dimethyl-4-phenyl-5-styrylfuran-2(5H)-one

(E)-3,5-dimethyl-4-phenyl-5-styrylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;92%
ethanol
64-17-5

ethanol

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

ethyl 2-methylcinnamate
7042-33-3, 7042-34-4, 1734-78-7

ethyl 2-methylcinnamate

Conditions
ConditionsYield
With acetyl chloride Reflux;91%
With sulfuric acid
With sulfuric acid for 2h; Reflux;
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

5-methyl-5-phenyl-1,2-hexadiene

5-methyl-5-phenyl-1,2-hexadiene

(E)-3,5-dimethyl-5-(3-methyl-3-phenylbut-1-en-1-yl)-4-phenylfuran-2(5H)-one

(E)-3,5-dimethyl-5-(3-methyl-3-phenylbut-1-en-1-yl)-4-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;91%
trifluoroethylamine
753-90-2

trifluoroethylamine

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

C12H12F3NO

C12H12F3NO

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;91%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

(E)-(2-bromoprop-1-en-1-yl)benzene
54624-37-2

(E)-(2-bromoprop-1-en-1-yl)benzene

Conditions
ConditionsYield
With hydrogen bromide; sodium nitrite In water; acetonitrile at 20℃; for 5h;90%
penta-3,4-dienoic acid ethyl ester
30332-99-1

penta-3,4-dienoic acid ethyl ester

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

(E)-ethyl 3-(2,4-dimethyl-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)acrylate

(E)-ethyl 3-(2,4-dimethyl-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)acrylate

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;90%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

C18H18O3

C18H18O3

Conditions
ConditionsYield
With 2C9H4NO6(3-)*3Fe(2+)*9H2O; trifluoroacetic anhydride In 1,2-dichloro-ethane at 90℃; for 5h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst;90%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

methylamine
74-89-5

methylamine

C11H13NO
105906-93-2

C11H13NO

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;89%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

1-(buta-2,3-dien-1-yl)-3-methylbenzene

1-(buta-2,3-dien-1-yl)-3-methylbenzene

(E)-3,5-dimethyl-5-(3-methylstyryl)-4-phenylfuran-2(5H)-one

(E)-3,5-dimethyl-5-(3-methylstyryl)-4-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;88%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

(E)-3-methyl-5-phenethyl-4-phenyl-5-styrylfuran-2(5H)-one

(E)-3-methyl-5-phenethyl-4-phenyl-5-styrylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;88%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

tert-butylamine
75-64-9

tert-butylamine

C14H19NO

C14H19NO

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;88%
3,4-pentadiene-1-ol
5557-87-9

3,4-pentadiene-1-ol

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

(E)-5-(3-hydroxyprop-1-en-1-yl)-3,5-dimethyl-4-phenylfuran-2(5H)-one

(E)-5-(3-hydroxyprop-1-en-1-yl)-3,5-dimethyl-4-phenylfuran-2(5H)-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 80℃; for 20h; Inert atmosphere; Sealed tube; Schlenk technique; stereoselective reaction;87%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

diphenyl acetylene
501-65-5

diphenyl acetylene

4-methyl-3,5,6-triphenyl-2H-pyran-2-on
1104516-50-8

4-methyl-3,5,6-triphenyl-2H-pyran-2-on

Conditions
ConditionsYield
With [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In tert-Amyl alcohol at 90℃; for 2h;86%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; tetrabutylammonium acetate In methanol at 60℃; for 12h; Electrochemical reaction;26%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

Tosyl isocyanate
4083-64-1

Tosyl isocyanate

C17H17NO3S

C17H17NO3S

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;86%
1-(p-toluenesulfonyl)-1H-indole
31271-90-6

1-(p-toluenesulfonyl)-1H-indole

α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

C25H21NO3S

C25H21NO3S

Conditions
ConditionsYield
With trifluoroacetic acid In 1,2-dichloro-ethane at 90℃; for 3h; Catalytic behavior; Reagent/catalyst; Time;86%
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

ethylamine
75-04-7

ethylamine

C12H15NO

C12H15NO

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;86%

1199-77-5Relevant articles and documents

Water-initiated hydrocarboxylation of terminal alkynes with CO2and hydrosilane

Wang, Meng-Meng,Lu, Sheng-Mei,Paridala, Kumaraswamy,Li, Can

supporting information, p. 1230 - 1233 (2021/02/09)

This work discloses a Cu(ii)-Ni(ii) catalyzed tandem hydrocarboxylation of alkynes with polysilylformate formed from CO2and polymethylhydrosiloxane that affords α,β-unsaturated carboxylic acids with up to 93% yield. Mechanistic studies indicate that polysilylformate functions as a source of CO and polysilanol. Besides, a catalytic amount of water is found to be critical to the reaction, which hydrolyzes polysilylformate to formic acid that induces the formation of Ni-H active species, thereby initiating the catalytic cycle.

Chrysamide B derivative with anti-tumor activity and preparation and application of Chrysamide B derivative

-

Paragraph 0053-0055; 0057, (2020/08/02)

The invention belongs to the field of medicinal chemistry, and particularly relates to a marine natural product Chrysamide B and a derivative thereof. The marine natural product Chrysamide B comprisesstereoisomers or pharmaceutically acceptable salts, solvates and prodrugs of the marine natural product Chrysamide B, general formulas are shown in a formula (I), a formula (II) and a formula (III).The invention also provides preparation and application of the compound. The compound has an anti-cancer effect; the compound has good inhibitory activity on digestive system cancers, leukemia, livertumors, non-small cell lung cancers, cervical cancers, breast cancers and the like and has the effects of inducing tumor cell apoptosis, activating apoptosis protein expression, retarding cycle, inhibiting proliferation and the like and is a potential antitumor drug.

Design, synthesis and biological evaluation of tetrazole-containing RXRα ligands as anticancer agents

Yan, Zhiqiang,Chong, Shuyi,Lin, Huiyun,Yang, Qian,Wang, Xin,Zhang, Weidong,Zhang, Xiaokun,Zeng, Zhiping,Su, Ying

, p. 562 - 575 (2019/01/10)

Nuclear receptor RXRα plays an important role in many biological and pathological processes. The nongenomic action of RXRα is implicated in many cancers. K-8008, a non-canonical RXRα ligand derived from sulindac, inhibits the TNFα-activated PI3K/AKT pathway by mediating the interaction between a truncated form of RXRα (tRXRα) and the p85α regulatory subunit of PI3K and exerts potent anticancer activity in animal model. Herein we report our studies of a novel series of K-8008 analogs as potential anticancer agents targeting RXRα. Two compounds 8b and 18a were identified to have slightly stronger binding to RXRα and improved apoptotic activities in breast cancer cells.

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