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14205-39-1

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14205-39-1 Usage

Chemical Properties

Crystals, yellowish-white

Uses

Different sources of media describe the Uses of 14205-39-1 differently. You can refer to the following data:
1. Methyl 3-aminocrotonate is used as intermediate for the syntheses of pharmaceuticals (e.g. 1,4-dihydropyridine derivatives) as well as for the manufacture of stabilizers and plastics. Product Data Sheet
2. Nitrendipine (N490150) metabolite. The pharmacokinetics of Nitrendipine was studied in the rat and 6 major metabolites were identified.
3. Methyl 3-aminocrotonate (Methyl 3-amino-2-butenoate) was used to synthesize 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity.

General Description

Methyl 3-aminocrotonate undergoes waste-free solid-state cascade reaction with crystalline ninhydrin.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 14205-39-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,2,0 and 5 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 14205-39:
(7*1)+(6*4)+(5*2)+(4*0)+(3*5)+(2*3)+(1*9)=71
71 % 10 = 1
So 14205-39-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO2/c1-4(6)3-5(7)8-2/h6H,3H2,1-2H3/b6-4+

14205-39-1SDS

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 Methyl 3-aminocrotonate

1.2 Other means of identification

Product number -
Other names METHYL 4-AMINOCROTONATE

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:14205-39-1 SDS

14205-39-1Synthetic route

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonium hydroxide In methanol; water for 16h; Heating;96%
With ammonia; acetic acid Product distribution / selectivity;94%
With ammonia In methanol at 0 - 10℃; for 4h; Large scale;85%
(-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate

(-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate

lithium enolate of methyl acetate
57570-85-1

lithium enolate of methyl acetate

A

(-)-methyl 3-((2S,3R)-1-(2-hydroxyethyl)-2-(indol-3-yl)piperidin-3-yl)-3-oxopropanoate

(-)-methyl 3-((2S,3R)-1-(2-hydroxyethyl)-2-(indol-3-yl)piperidin-3-yl)-3-oxopropanoate

B

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
Stage #1: (-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Claisen Condensation;
Stage #2: lithium enolate of methyl acetate at -78 - 20℃; for 20.0833h; Claisen Condensation;
A 72%
B 102 mg
(E)-methyl 3-chloro-2-butenoate
6372-01-6

(E)-methyl 3-chloro-2-butenoate

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonia at 100℃;
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

A

acetoacetamido
5977-14-0

acetoacetamido

B

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonia
β--crotonic acid methyl ester

β--crotonic acid methyl ester

A

butanamide
541-35-5

butanamide

B

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonia
ammonia
7664-41-7

ammonia

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 20℃; for 6h;
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

acetic acid
64-19-7

acetic acid

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

C13H16INO4

C13H16INO4

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 20℃; for 0.0833333h;100%
C11H7Cl3O4

C11H7Cl3O4

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

dimethyl (S)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate

dimethyl (S)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate

Conditions
ConditionsYield
With (+)-(R,S)-Fused-BTM; diphenyl-phosphinic acid In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;99%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

acetaldehyde
75-07-0

acetaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

2,4,6-Trimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-1,4-dihydropyridine
53632-38-5

2,4,6-Trimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-1,4-dihydropyridine

Conditions
ConditionsYield
In ethanol at 100℃;98.2%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 3-aminocrotonate p-toluenesulfonate
650602-19-0

methyl 3-aminocrotonate p-toluenesulfonate

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonic acid In toluene for 2h; Heating / reflux;
Stage #2: methyl 3-aminocrotonate In toluene at 5 - 20℃; for 1.5h;
98.2%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

m-nifedipine
21881-77-6

m-nifedipine

Conditions
ConditionsYield
With sodium tosylate In water for 0.3h; Reagent/catalyst; Time; Hantzsch Dihydropyridine Synthesis; Microwave irradiation; Reflux; Green chemistry;98%
for 7h; microwave irradiation;59.4%
In ethanol at 90℃; Hantzsch condensation reaction;20%
3-[1-Ethoxycarbonyloxy-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

3-[1-Ethoxycarbonyloxy-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

3-(3-amino-2-methoxycarbonyl-but-2-enylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

3-(3-amino-2-methoxycarbonyl-but-2-enylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 2.5h; Heating;98%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl (Z)-3-amino-2-(2-chloroacetyl)but-2-enoate

methyl (Z)-3-amino-2-(2-chloroacetyl)but-2-enoate

Conditions
ConditionsYield
With pyridine In diethyl ether at -25 - 0℃; for 4.75h;98%
C12H9Cl3O4

C12H9Cl3O4

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

4-ethyl 3-methyl (S)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate

4-ethyl 3-methyl (S)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate

Conditions
ConditionsYield
With (+)-(R,S)-Fused-BTM; diphenyl-phosphinic acid In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;98%
5-Methylfurfural
620-02-0

5-Methylfurfural

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

1,4-dihydro-2,6-dimethyl-4-(5'-methyl-furan-2'-yl)pyridine-3,5-dicarboxylic acid dimethyl ester
296266-88-1

1,4-dihydro-2,6-dimethyl-4-(5'-methyl-furan-2'-yl)pyridine-3,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 2h; Hantzsch Dihydropyridine Synthesis;97%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

dimedone
126-81-8

dimedone

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 2,7,7-trimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

methyl 2,7,7-trimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions
ConditionsYield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 1h; Hantzsch Dihydropyridine Synthesis;96%
With Fe(1+)*HO4S(1-)*12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;92%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

(4''S)-4-(3''-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-ylmethyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
596828-11-4

(4''S)-4-(3''-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-ylmethyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With 4 A molecular sieve In methanol at 90℃; for 24h; Hantzsch cyclocondensation;95%
2-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

propan-1-ol
71-23-8

propan-1-ol

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

C17H22N2O4

C17H22N2O4

Conditions
ConditionsYield
Stage #1: propan-1-ol; 2,2,6-trimethyl-4H-1,3-dioxin-4-one With N,N-dimethyl-formamide In 5,5-dimethyl-1,3-cyclohexadiene at 60 - 143℃; for 8h;
Stage #2: 2-pyrrole aldehyde; methyl 3-aminocrotonate In 5,5-dimethyl-1,3-cyclohexadiene at 85 - 320℃; for 6h;
Stage #3: With cinchonidine In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 142℃; for 10h; Temperature; Reagent/catalyst;
95%
benzaldehyde
100-52-7

benzaldehyde

dimedone
126-81-8

dimedone

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-4-phenylquinoline-3-carboxylate

methyl 1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-5-oxo-4-phenylquinoline-3-carboxylate

Conditions
ConditionsYield
With Fe(1+)*HO4S(1-)*12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;94%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester
39562-70-4

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Conditions
ConditionsYield
With sodium tosylate In water for 0.4h; Reagent/catalyst; Time; Hantzsch Dihydropyridine Synthesis; Microwave irradiation; Reflux; Green chemistry;94%
With C21H38N(1+)*Mo11O40PV(4-)*3H(1+) In ethanol at 78℃; for 8h; Catalytic behavior; Hantzsch Pyridine Synthesis; Green chemistry;78%
Hantzsch Dihydropyridine Synthesis; Darkness; Reflux;59%
C10H4Cl3F3O2

C10H4Cl3F3O2

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl (S)-2-methyl-6-oxo-4-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate

methyl (S)-2-methyl-6-oxo-4-(trifluoromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate

Conditions
ConditionsYield
With (+)-(R,S)-Fused-BTM; diphenyl-phosphinic acid In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; enantioselective reaction;94%
dimedone
126-81-8

dimedone

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 1,4,5,6,7,8‐hexahydro‐4‐(3‐methoxyphenyl)‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

methyl 1,4,5,6,7,8‐hexahydro‐4‐(3‐methoxyphenyl)‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

Conditions
ConditionsYield
With Fe(1+)*HO4S(1-)*12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;93%
dimedone
3471-13-4

dimedone

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 4‐(4‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

methyl 4‐(4‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

Conditions
ConditionsYield
With ammonium acetate In water at 45℃; for 2h; Green chemistry;93%
dimedone
126-81-8

dimedone

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
312585-92-5

methyl 4-(2-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions
ConditionsYield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 2h; Hantzsch Dihydropyridine Synthesis;93%
4-fluorobenzenediazonium tetrafluoroborate
459-45-0

4-fluorobenzenediazonium tetrafluoroborate

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazole-4-carboxylate

methyl 2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazole-4-carboxylate

Conditions
ConditionsYield
With caesium carbonate; copper dichloride In acetonitrile at 20℃; for 0.5h;93%
C16H14ClNO2S

C16H14ClNO2S

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 4-[2-(2-chlorophenylthiazol)-2-yl]-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
1076202-58-8

methyl 4-[2-(2-chlorophenylthiazol)-2-yl]-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions
ConditionsYield
In methanol modified Hantzsch synthesis; Reflux; Darkness;92%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

dimedone
126-81-8

dimedone

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

2,7,7-trimethyl-5-oxo-4-(4-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester

2,7,7-trimethyl-5-oxo-4-(4-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With Fe(1+)*HO4S(1-)*12H2O*H3N In ethanol at 20℃; for 4.5h; Hantzsch reaction;92%
dimedone
3471-13-4

dimedone

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 4-(2‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

methyl 4-(2‐chlorophenyl)‐1,4,5,6,7,8‐hexahydro‐2,7,7‐trimethyl‐5‐oxoquinoline‐3‐carboxylate

Conditions
ConditionsYield
With ammonium acetate In water at 45℃; for 2.5h; Green chemistry;92%
α-bromoacetophenone
70-11-1

α-bromoacetophenone

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid methyl ester
28168-20-9

2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 130℃; for 0.166667h; Reagent/catalyst; Solvent; Microwave irradiation;92%
dimedone
126-81-8

dimedone

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat
126412-02-0

1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat

Conditions
ConditionsYield
With ZnNO3 supported on MCM-41 In ethanol at 20℃; for 2h; Hantzsch Dihydropyridine Synthesis;92%
2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate
102993-38-4

2-cyanoethyl 2-(3-nitrobenzylidene)-3-oxobutanoate

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester
75130-24-4

2,6-dimethyl-4-(3-nitrophenyl)-5-methoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester

Conditions
ConditionsYield
In methanol for 2h; Reflux;91.1%
acrolein
107-02-8

acrolein

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 2-methylnicotinate
65719-09-7

methyl 2-methylnicotinate

Conditions
ConditionsYield
In toluene at 120℃; for 3h; Solvent; Temperature; Sealed tube;91%
With piperidine; sulfuric acid; nitric acid 1.) ethanol, 24 h, reflux, 2.) water, 10 min, water bath; Yield given. Multistep reaction;
tert-butyl 2,4-dioxopiperidine-1-carboxylate
845267-78-9

tert-butyl 2,4-dioxopiperidine-1-carboxylate

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

6-tert-butyl 3-methyl 4-(3-methoxyphenyl)-7,8-dihydro-2-methyl-5-oxo-1,6-naphthy-ridine-3,6(1H,4H,5H)-dicarboxylate

6-tert-butyl 3-methyl 4-(3-methoxyphenyl)-7,8-dihydro-2-methyl-5-oxo-1,6-naphthy-ridine-3,6(1H,4H,5H)-dicarboxylate

Conditions
ConditionsYield
at 80℃; for 8h; Ionic liquid; Green chemistry;91%
1-(3,4,5-trimethoxyphenyl)-2-bromoethanone
51490-01-8

1-(3,4,5-trimethoxyphenyl)-2-bromoethanone

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

methyl 2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-carboxylate
1419101-66-8

methyl 2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-carboxylate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 130℃; for 0.233333h; Microwave irradiation;91%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

dimedone
126-81-8

dimedone

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

A

methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

B

9-(4-nitrophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-dione
40588-46-3

9-(4-nitrophenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-dione

Conditions
ConditionsYield
With C22H25F6N5S; ammonium acetate In dichloromethane at 20℃; for 1h; Reagent/catalyst; Hantzsch Dihydropyridine Synthesis;A 91%
B 3%

14205-39-1Downstream Products

14205-39-1Relevant articles and documents

Highly enantioselective rhodium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites

Pena, Diego,Minnaard, Adriaan J.,De Vries, Johannes G.,Feringa, Ben L.

, p. 14552 - 14553 (2002)

New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-β-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems were established for (E)-β-(acylamino)acrylates (98-99% ee) and (Z)-β-(acylamino)acrylates (92-95% ee) based on phosphoramidites 2 and 3, respectively. Copyright

Cytotoxic and multidrug resistance reversal activities of novel 1,4-dihydropyridines against human cancer cells

Shekari, Farnaz,Sadeghpour, Hossein,Javidnia, Katayoun,Saso, Luciano,Nazari, Farhad,Firuzi, Omidreza,Miri, Ramin

, p. 233 - 244 (2015)

Multidrug resistance (MDR) caused by P-glycoprotein (P-gp, ABCB1, MDR-1) transporter over-expression in cancer cells substantially limits the effectiveness of chemotherapy. 1,4-Dihydropyridines (DHPs) derivatives possess several pharmacological activities. In this study, 18 novel asymmetrical DHPs bearing 3-pyridyl methyl carboxylate and alkyl carboxylate moieties at C3 and C5 positions, respectively, as well as nitrophenyl or hetero aromatic rings at C4 were synthesized and tested for MDR reversal with the aim of establishing a structure-activity relationship (SAR) for these agents. Effect of these compounds on P-gp mediated MDR was assessed in P-gp over-expressing MES-SA/DX5 doxorubicin resistant cells by flow cytometric detection of rhodamine 123 efflux. MDR reversal was further examined as the alteration of doxorubicin's IC50 in MES-SA/DX5 cells in the presence of DHPs by MTT assay and was compared to nonresistant MES-SA cells. Direct anticancer effect was examined against 4 human cancer cells including HL-60, K562, MCF-7 and LS180. Calcium channel blocking (CCB) activity was also measured as a potential side effect. Most DHPs, particularly compounds bearing 3-nitrophenyl (A2B2 and A3B2) and 4-nitrophenyl (A3B1 and A4B1) moieties at C4 significantly inhibited rhodamine 123 efflux at 5-25 μM, showing that the mechanism of MDR reversal by these agents is P-gp transporter modulation. Same derivatives were also able to selectively lower the resistance of MES-SA/DX5 to doxorubicin. A2B2 bearing ethyl carboxylate at C5 had also high direct antitumoral effect (IC50 range: 3.77-15.60 μM). Our findings suggest that SAR studies of DHPs may lead to the discovery of novel MDR reversal agents.

Reversal of multidrug resistance in cancer cells by novel asymmetrical 1,4-dihydropyridines

Firuzi, Omidreza,Javidnia, Katayoun,Mansourabadi, Elham,Saso, Luciano,Mehdipour, Ahmad Reza,Miri, Ramin

, p. 1392 - 1402 (2013)

Multidrug resistance (MDR) is an important obstacle that limits the efficacy of chemotherapy in many types of cancer. In this study, 14 novel asymmetrical DHPs possessing pyridyl alkyl carboxylate substitutions at C 3 and alkyl carboxylate groups at C5 in addition to a nitroimidazole or nitrophenyl moiety at C4 position were synthesized. Calcium channel blocking (CCB) activity was measured in guinea pig ileal longitudinal smooth muscle. Cytotoxicity was tested on 4 human cancer cell lines, while MDR reversal capacity was examined on P-glycoprotein overexpressing doxorubicin resistant MES-SA-DX5 and compared with non-resistant MES-SA cells. Compounds showed different CCB (IC50: 29.3 nM-4.75 μM) and cytotoxic activities (IC50: 6.4 to more than 100 μM). Several compounds having nitrophenyl moiety at C4, could significantly reverse resistance to doxorubicin at 0.5 and 1 μM. The most active ones were 7e and 7g containing ethyl carboxylate and isopropyl carboxylate at C 5, respectively. CCB activity, which is considered an undesirable effect for these agents, of 7e and 7g were 33 and 20 times lower than nifedipine, respectively. In conclusion, the newly synthesized asymmetrical DHP compounds showed promising MDR reversal and antitumoral activities with low CCB effects and could be of therapeutic value in drug resistant cancer.

Based on the three-step synthesis process of preparation of the nitrendipine (by machine translation)

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Paragraph 0020-0021; 0031-0033; 0039; 0045; 0051, (2019/02/04)

The invention discloses a method based on three-step preparation of the nitrendipine synthesis process, comprising the following steps: S1 ammoniation reaction: liquid ammonia with methyl acetoacetate reflect the generated β - amino-crotonic acid methyl ester; S2 condensation reaction: will be m formaldehyde and acetyl ethyl acetate in the catalyst piperidine and glacial acetic acid under the action of the condensation reaction to obtain the pure 2 - (3 - nitryl asia phenmethyl) - acetyl ethyl acetate; S3 ring-closure reaction: the β - amino-crotonic acid methyl ester with 2 - (3 - nitryl asia phenmethyl) - acetyl ethyl acetate in the catalyst diisopropyl ethylamine/glacial acetic acid under the action of the Michael reaction, then molecule in cyclization to obtain nitrendipine; S4 refining, the invention - nitrobenzaldehyde between (SM1), acetyl ethyl acetate (SM2) and methyl acetoacetate (SM3) as the starting raw material preparation, heating the ring, three-step reaction qualified products can be obtained nitrendipine, not containing special reaction conditions. (by machine translation)

A new process for the preparation of felodipine (by machine translation)

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Paragraph 0024; 0026; 0027, (2018/07/06)

The invention discloses a new process for the preparation of felodipine, including: 1) to acetyl acetic acid methyl ester as the raw material, to prepare the 3 - amino-crotonic acid methyl ester; 2) to 2, 3 - dichloro formaldehyde and acetyl acetic acid ethyl ester as the raw material, to prepare the 2, 3 - two chlorine asia phenmethyl acetyl ethyl acetate; 3) to 2, 3 - two chlorine asia phenmethyl acetyl ethyl acetate, 3 - amino-crotonic acid methyl ester as the raw material, prepare the felodipine. The invention of the preparation process of felodipine, intermediates for the preparation of 3 - amino-crotonic acid methyl ester having a melting point of 83 - 35 °C, far higher than the widely used of the intermediate 3 - amino-crotonic acid ethyl ester (33 - 35 °C), therefore the stability can be improved, convenient in a wider temperature conditions production and storage, is more favorable to the industrialized production and application. At the same time, the process high product yield, high purity, step is simple, easy to operate, and has good practicability. (by machine translation)

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