Product Name

  • Name

    3-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione

  • EINECS
  • CAS No. 5845-66-9
  • Article Data8
  • CAS DataBase
  • Density 1.308 g/cm3
  • Solubility
  • Melting Point 240℃
  • Formula C11H12N2O3
  • Boiling Point 623.1 °C at 760 mmHg
  • Molecular Weight 220.228
  • Flash Point 330.7 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 5845-66-9 (3-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione)
  • Hazard Symbols
  • Synonyms 3-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione;3-((4-Hydroxyphenyl)methyl)-2,5-piperazinedione;
  • PSA 78.43000
  • LogP 0.20690

Synthetic route

cyclo(L-tyrosine(OBn)-glycine)
1628630-12-5

cyclo(L-tyrosine(OBn)-glycine)

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;92%
CF3CO2H*H-L-Tyr-Gly-OMe

CF3CO2H*H-L-Tyr-Gly-OMe

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
With 4-methyl-morpholine; acetic acid In iso-butanol at 120℃; for 3h;43%
N-Gly-Tyr
658-79-7

N-Gly-Tyr

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Boc-Tyr-Gly-OEt
67208-98-4

Boc-Tyr-Gly-OEt

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
With 4-methyl-morpholine; hydrogenchloride; acetic acid 1.) dioxane, r.t., 30 min; 2.) 2-butanol, reflux, 3 h; Yield given. Multistep reaction;
Boc-Tyr-OH
3978-80-1

Boc-Tyr-OH

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / N,N'-dicyclohexylcarbodiimide, 1-hydroxybenztriazole
2: 1.) 4N HCl; 2.) N-methylmorpholine / 2.) 0.1M AcOH / 1.) dioxane, r.t., 30 min; 2.) 2-butanol, reflux, 3 h
View Scheme
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2: dichloromethane / 1 h / 20 °C / Inert atmosphere
3: acetic acid; 4-methyl-morpholine / iso-butanol / 3 h / 120 °C
View Scheme
FLQLYGLPETGY-isoacyl-Hse(Bz)-NH2
1594922-38-9

FLQLYGLPETGY-isoacyl-Hse(Bz)-NH2

GGGGAEW-NH2
1594873-76-3

GGGGAEW-NH2

A

C22H26N4O6
1594962-96-5

C22H26N4O6

B

C11H14N2O3
1195407-21-6

C11H14N2O3

C

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
With recombinant sortase A In aq. buffer at 21℃; pH=8;
...Expand
BOC-Tyr(OBzl)-Gly-OEt
40356-35-2

BOC-Tyr(OBzl)-Gly-OEt

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; methanol / 0.17 h / 170 °C / Microwave irradiation
2: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine
2130-96-3

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
2: water; methanol / 0.17 h / 170 °C / Microwave irradiation
3: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
View Scheme
Boc-L-Tyr-Gly-OMe
7733-20-2

Boc-L-Tyr-Gly-OMe

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 1 h / 20 °C / Inert atmosphere
2: acetic acid; 4-methyl-morpholine / iso-butanol / 3 h / 120 °C
View Scheme
L-tyrosine ethyl ester
949-67-7

L-tyrosine ethyl ester

chloroacetyl chloride
79-04-9

chloroacetyl chloride

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

Conditions
ConditionsYield
With ammonia Multistep reaction;
prenyl bromide
870-63-3

prenyl bromide

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

cyclo-(glycyl-t-tyrosyl) 4,4-dimethylallyl ether
112900-76-2

cyclo-(glycyl-t-tyrosyl) 4,4-dimethylallyl ether

Conditions
ConditionsYield
With caesium carbonate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 12h;73%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;46%
With sodium hydride In dimethyl sulfoxide 0 deg C, then room t., 20 h;23 mg
dimethyl sulfate
77-78-1

dimethyl sulfate

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

3-<(4-methoxyphenyl)methyl>-1,4-dimethylpiperazine-2,5-dione
128520-01-4

3-<(4-methoxyphenyl)methyl>-1,4-dimethylpiperazine-2,5-dione

Conditions
ConditionsYield
With sodium hydride DMSO-THF; Multistep reaction;
3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

methyl iodide
74-88-4

methyl iodide

3-<(4-methoxyphenyl)methyl>-1,4-dimethylpiperazine-2,5-dione
128520-01-4

3-<(4-methoxyphenyl)methyl>-1,4-dimethylpiperazine-2,5-dione

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide for 18h; Ambient temperature;
N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide

N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
5845-66-9

3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione

A

Gly-L-FDAA

Gly-L-FDAA

B

DAA-L-Tyr-OH

DAA-L-Tyr-OH

Conditions
ConditionsYield
Stage #1: 3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione With hydrogenchloride In water at 125℃; for 24h;
Stage #2: N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide With sodium hydrogencarbonate In water; acetone at 40℃; for 1h;
...Expand

3-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione Specification

The CAS register number of Cyclo(Gly-Tyr) is 5845-66-9. It also can be called as 3-((4-Hydroxyphenyl)methyl)-2,5-piperazinedione and the IUPAC name about this chemical is 3-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione. The molecular formula about this chemical is C11H12N2O3 and the molecular weight is 220.22788.

Physical properties about Cyclo(Gly-Tyr) are: (1)ACD/LogP: -1.11; (2)ACD/LogD (pH 5.5): -1.11; (3)ACD/LogD (pH 7.4): -1.12; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 5.9; (7)ACD/KOC (pH 7.4): 5.89; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 49.85 Å2; (12)Index of Refraction: 1.585; (13)Molar Refractivity: 56.45 cm3; (14)Molar Volume: 168.2 cm3; (15)Polarizability: 22.37x10-24cm3; (16)Surface Tension: 53.2 dyne/cm; (17)Density: 1.308 g/cm3; (18)Flash Point: 330.7 °C; (19)Enthalpy of Vaporization: 95.67 kJ/mol; (20)Boiling Point: 623.1 °C at 760 mmHg; (21)Vapour Pressure: 4.04E-16 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NCC(=O)NC1Cc2ccc(O)cc2
(2)InChI: InChI=1/C11H12N2O3/c14-8-3-1-7(2-4-8)5-9-11(16)12-6-10(15)13-9/h1-4,9,14H,5-6H2,(H,12,16)(H,13,15)(3)InChIKey: QHLSAVHDWSYPEP-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C11H12N2O3/c14-8-3-1-7(2-4-8)5-9-11(16)12-6-10(15)13-9/h1-4,9,14H,5-6H2,(H,12,16)(H,13,15)
(5)Std. InChIKey: QHLSAVHDWSYPEP-UHFFFAOYSA-N

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