(fluorenylmethoxy)carbonyl chloride
2-(7-amino-2-oxo-2H-chromen-4-yl)acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
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 |
m-Hydroxyaniline
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
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 |
ethyl N-(3-hydroxyphenyl)carbamate
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
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 |
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Leu-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
N-Fmoc L-Phe
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Ser(tBu)-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-(tBu)Asp-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-(tBu)Asp-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Glu(OtBu)-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Ile-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Tyr(tBu)-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Lys(tert-butoxycarbonyl)
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Lys(tert-butoxycarbonyl)
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Lys(tert-butoxycarbonyl)
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Lys(tert-butoxycarbonyl)
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Lys(tert-butoxycarbonyl)
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Thr(tBu)-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
L-Asn(Trt)
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-L-Gln(Trt)-OH
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
acetic acid
Fmoc-L-His(Boc)-OH
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
acetic acid
3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
tert-butyl (3-aminopropoxy)carbamate
N-(fluoren-9-ylmethoxycarbonyl)glycine
acetic acid
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
Multistep reaction.; |
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide Rink Amide AM resin; |
N-(9-fluorenylmethoxycarbonyl)-D-alanine
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
C14H15N3O4
Conditions | Yield |
---|---|
Stage #1: 7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 24h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(9-fluorenylmethoxycarbonyl)-D-alanine Further stages; |
N-(9-fluorenylmethoxycarbonyl)-D-leucine
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
C17H21N3O4
Conditions | Yield |
---|---|
Stage #1: 7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 24h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(9-fluorenylmethoxycarbonyl)-D-leucine Further stages; |
Fmoc-D-Phe-OH
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
C20H19N3O4
Conditions | Yield |
---|---|
Stage #1: 7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 24h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: Fmoc-D-Phe-OH Further stages; |
(R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid
C16H17N3O4
Conditions | Yield |
---|---|
Stage #1: 7-N-(fluoren-9-ylmethoxycarbonyl)-aminocoumarin-4-acetic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 24h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester Further stages; |
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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