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7-N-Fmoc-aminocoumarin-4-acetic acid

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Name

7-N-Fmoc-aminocoumarin-4-acetic acid

EINECS N/A
CAS No. 378247-75-7 Density 1.419 g/cm3
PSA 105.84000 LogP 4.85410
Solubility N/A Melting Point N/A
Formula C26H19NO6 Boiling Point 660.549 °C at 760 mmHg
Molecular Weight 441.44 Flash Point 353.288 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 378247-75-7 ([7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid) Hazard Symbols N/A
Synonyms

7-N-Fmoc-aminocoumarin-4-acetic acid

Article Data 5

7-N-Fmoc-aminocoumarin-4-acetic acid Synthetic route

28920-43-6

(fluorenylmethoxy)carbonyl chloride

85157-21-7

2-(7-amino-2-oxo-2H-chromen-4-yl)acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

Conditions
ConditionsYield
Stage #1: 2-(7-amino-2-oxo-2H-chromen-4-yl)acetic acid With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Heating;
Stage #2: (fluorenylmethoxy)carbonyl chloride In dichloromethane at 20℃; for 11h; Further stages.;
88%
With sodium hydrogencarbonate In water; acetone
With sodium hydrogencarbonate In water; acetone at 0 - 20℃;
Stage #1: 2-(7-amino-2-oxo-2H-chromen-4-yl)acetic acid With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Reflux;
Stage #2: (fluorenylmethoxy)carbonyl chloride In dichloromethane at 20℃;
Stage #3: With hydrogenchloride In dichloromethane; water pH=2;
1.43 g
591-27-5

m-Hydroxyaniline

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethyl acetate / 1 h / Reflux
2.1: sulfuric acid / 12 h / 20 °C / Cooling with ice
3.1: sodium hydroxide / water / Reflux
4.1: N-ethyl-N,N-diisopropylamine; chloro-trimethyl-silane / dichloromethane / 3 h / Reflux
4.2: 20 °C
4.3: pH 2
View Scheme
7159-96-8

ethyl N-(3-hydroxyphenyl)carbamate

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / 12 h / 20 °C / Cooling with ice
2.1: sodium hydroxide / water / Reflux
3.1: N-ethyl-N,N-diisopropylamine; chloro-trimethyl-silane / dichloromethane / 3 h / Reflux
3.2: 20 °C
3.3: pH 2
View Scheme
378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

Rink Amide AM resin

Rink Amide AM resin

[7-N-(fluorenylmethoxycarbonyl)aminocoumarin-4-CH2CONH]-Rink Amide AM resin

[7-N-(fluorenylmethoxycarbonyl)aminocoumarin-4-CH2CONH]-Rink Amide AM resin

Conditions
ConditionsYield
With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide
228245-16-7

tert-butyl (3-aminopropoxy)carbamate

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

35661-60-0

Fmoc-Leu-OH

64-19-7

acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

(S)-2-{(S)-2-[(S)-2-((S)-2-Acetylamino-propionylamino)-6-amino-hexanoylamino]-4-methyl-pentanoylamino}-6-amino-hexanoic acid [4-({[(3-aminooxy-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-2-oxo-2H-chromen-7-yl]-amide

Conditions
ConditionsYield
Multistep reaction.;
228245-16-7

tert-butyl (3-aminopropoxy)carbamate

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

64-19-7

acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

(S)-1-((S)-2-Acetylamino-propionyl)-pyrrolidine-2-carboxylic acid ((S)-1-{(S)-5-amino-1-[4-({[(3-aminooxy-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-2-oxo-2H-chromen-7-ylcarbamoyl]-pentylcarbamoyl}-ethyl)-amide

Conditions
ConditionsYield
Multistep reaction.;
228245-16-7

tert-butyl (3-aminopropoxy)carbamate

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

64-19-7

acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

(S)-2-{(S)-2-[(S)-2-((S)-2-Acetylamino-propionylamino)-3-(3H-imidazol-4-yl)-propionylamino]-propionylamino}-6-amino-hexanoic acid [4-({[(3-aminooxy-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-2-oxo-2H-chromen-7-yl]-amide

Conditions
ConditionsYield
Multistep reaction.;
228245-16-7

tert-butyl (3-aminopropoxy)carbamate

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

35661-40-6

N-Fmoc L-Phe

64-19-7

acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

(S)-2-{(S)-2-[(S)-2-((S)-2-Acetylamino-propionylamino)-3-hydroxy-propionylamino]-3-phenyl-propionylamino}-6-amino-hexanoic acid [4-({[(3-aminooxy-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-2-oxo-2H-chromen-7-yl]-amide

Conditions
ConditionsYield
Multistep reaction.;
228245-16-7

tert-butyl (3-aminopropoxy)carbamate

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

71989-33-8

Fmoc-Ser(tBu)-OH

64-19-7

acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

(S)-2-{(S)-2-[(S)-2-((S)-2-Acetylamino-propionylamino)-3-hydroxy-propionylamino]-5-guanidino-pentanoylamino}-6-amino-hexanoic acid [4-({[(3-aminooxy-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-2-oxo-2H-chromen-7-yl]-amide

Conditions
ConditionsYield
Multistep reaction.;
228245-16-7

tert-butyl (3-aminopropoxy)carbamate

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

71989-14-5

Fmoc-(tBu)Asp-OH

64-19-7

acetic acid

378247-75-7

7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid

(S)-4-((2S,3S)-2-Acetylamino-3-methyl-pentanoylamino)-5-((S)-2-{(S)-1-[4-({[(3-aminooxy-propylcarbamoyl)-methyl]-carbamoyl}-methyl)-2-oxo-2H-chromen-7-ylcarbamoyl]-2-carboxy-ethylcarbamoyl}-pyrrolidin-1-yl)-5-oxo-pentanoic acid

Conditions
ConditionsYield
Multistep reaction.;

7-N-Fmoc-aminocoumarin-4-acetic acid Specification

The 7-N-Fmoc-aminocoumarin-4-acetic acid is an organic compound with the formula C26H19NO6. The IUPAC name of this chemical is 2-[7-(9H-fluoren-9-ylmethoxycarbonylamino)-2-oxochromen-4-yl]acetic acid. With the CAS registry number 378247-75-7, it is also named as [7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid.

Physical properties about 7-N-Fmoc-aminocoumarin-4-acetic acid are: (1)ACD/LogP: 4.45; (2)ACD/LogD (pH 5.5): 3; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 65; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 289; (7)ACD/KOC (pH 7.4): 5; (8)#H bond acceptors: 7; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 101.93 Å2; (12)Index of Refraction: 1.687; (13)Molar Refractivity: 118.479 cm3; (14)Molar Volume: 311.087 cm3; (15)Polarizability: 46.969×10-24cm3; (16)Surface Tension: 66.697 dyne/cm; (17)Density: 1.419 g/cm3; (18)Flash Point: 353.288 °C; (19)Enthalpy of Vaporization: 102.126 kJ/mol; (20)Boiling Point: 660.549 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc2c(c1)-c3ccccc3C2COC(=O)Nc4ccc5c(cc(=O)oc5c4)CC(=O)O
(2)InChI: InChI=1/C26H19NO6/c28-24(29)11-15-12-25(30)33-23-13-16(9-10-17(15)23)27-26(31)32-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-10,12-13,22H,11,14H2,(H,27,31)(H,28,29)
(3)InChIKey: RCUKLQDGAASIAX-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C26H19NO6/c28-24(29)11-15-12-25(30)33-23-13-16(9-10-17(15)23)27-26(31)32-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-10,12-13,22H,11,14H2,(H,27,31)(H,28,29)
(5)Std. InChIKey: RCUKLQDGAASIAX-UHFFFAOYSA-N

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