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N-Acetyl-D-phenylalanine

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Name

N-Acetyl-D-phenylalanine

EINECS 233-447-7
CAS No. 10172-89-1 Density 1.2 g/cm3
PSA 66.40000 LogP 1.20930
Solubility N/A Melting Point 167 °C
Formula C11H13NO3 Boiling Point 453.944 °C at 760 mmHg
Molecular Weight 207.229 Flash Point 228.338 °C
Transport Information N/A Appearance White Solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 10172-89-1 (N-ACETYL-D-PHENYLALANINE) Hazard Symbols N/A
Synonyms

Alanine,N-acetyl-3-phenyl-, D- (8CI);(-)-2-Acetylamino-3-phenylpropanoic acid;(-)-N-Acetyl-L-phenylalanine;(-)-N-Acetylphenylalanine;(R)-(-)-N-Acetylphenylalanine;(R)-2-Acetylamino-3-phenylpropionic acid;(R)-N-Acetylphenylalanine;D-(-)-N-Acetylphenylalanine;D-N-Acetylphenylalanine;N-Acetyl-(R)-phenylalanine;N-Acetyl-3-phenyl-D-alanine;NSC 523830;(R)-2-(Acetylamino)-3-phenylpropanoic acid;

Article Data 220

N-Acetyl-D-phenylalanine Synthetic route

55065-02-6, 64590-80-3, 5469-45-4

N-acetamido cinnamic acid

10172-89-1

(R)-N-acetylphenylalanin

Conditions
ConditionsYield
With hydrogen; triethylamine; [Rh(CLPL-S)(COD)]BF4 In methanol at 40℃; under 15001.5 Torr; for 22h; Product distribution / selectivity;100%
In ethanol98%
With hydrogen; [Rh(norbornadiene)2]BF4 In methanol at 30℃; under 750.06 Torr;96%

(Z)-2-acetamidocinnamic acid

10172-89-1

(R)-N-acetylphenylalanin

Conditions
ConditionsYield
96.2%
55065-02-6, 64590-80-3, 5469-45-4

N-acetamido cinnamic acid

A

10172-89-1

(R)-N-acetylphenylalanin

B

2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

Conditions
ConditionsYield
With [Rh(cod)(Xylophos)](1+)*BF4(1-); hydrogen In methanol at 19.85℃; under 760 Torr; for 6h;A 11%
B 89%
With hydrogen; (1+); Dowex HCR-S In methanol; water at 50℃; under 15001.2 Torr; Product distribution; other rhodium(I)-complexes, various reaction conditions: time, pressure and temperatures; other derivatives of acetamidoacryl acid;
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; optically active phosphine In methanol at 20 - 30℃; under 825.07 Torr; for 72h; Product distribution; various di- and triphosphines, other temperatures and times;
21156-62-7, 3618-96-0, 62436-70-8

N-acetylphenylalanine methyl ester

10172-89-1

(R)-N-acetylphenylalanin

Conditions
ConditionsYield
for 36h; carbonate hydrolyase EC 4.2.2.1 (bovine carbonic anhydrase, BCA), pH 7.5;81%
4134-09-2

ethyl N-acetyl-DL-phenylalaninate

A

10172-89-1

(R)-N-acetylphenylalanin

B

2018-61-3

(S)-2-acetylamino-3-phenylpropanoic acid

C

2361-96-8, 4134-09-2, 57772-79-9, 20918-84-7

(R)-ethyl N-acetylphenylalanine

Conditions
ConditionsYield
With water In ethanol at 25℃; for 2h; Microbiological reaction; optical yield given as %ee; enantioselective reaction;A n/a
B n/a
C 45%
at 35℃; for 48h; in the present of Saccharomyces cerevisiae Hansen; Yield given. Yields of byproduct given;
28069-46-7

D-phenylalanine hydrochloride

75-36-5

acetyl chloride

10172-89-1

(R)-N-acetylphenylalanin

Conditions
ConditionsYield
With sodium hydroxide; water at 0℃; for 1h;41%
2901-75-9

(R,S)-N-acetyl phenylalanine

131348-01-1

(1S)-endo-fenchylamine

10172-89-1

(R)-N-acetylphenylalanin

2901-75-9

(R,S)-N-acetyl phenylalanine

10172-89-1

(R)-N-acetylphenylalanin

673-06-3

D-(R)-phenylalanine

108-24-7

acetic anhydride

10172-89-1

(R)-N-acetylphenylalanin

Conditions
ConditionsYield
With sodium hydroxide
at 0 - 4℃; for 3h; Acetylation;
With sodium hydroxide In water at 0 - 25℃; for 0.5h; pH=11 - 12;
With sodium hydroxide In water at 20℃; pH=14;
2901-75-9

(R,S)-N-acetyl phenylalanine

106-49-0

p-toluidine

A

10172-89-1

(R)-N-acetylphenylalanin

B

N-acetyl-L-phenylalanine p-toluidide

Conditions
ConditionsYield
With papain

N-Acetyl-D-phenylalanine Specification

The N-Acetyl-D-phenylalanine, with the CAS registry number 10172-89-1, is also known as (R)-2-(Acetylamino)-3-phenylpropanoic acid. It belongs to the product categories of Amino Acid Derivatives; Amino Acids; Ac-Amino Acids; Amino Acids (N-Protected); Biochemistry; A - H; Modified Amino Acids; Amino Acids & Derivatives; Chiral Reagents. Its EINECS number is 233-447-7. This chemical's molecular formula is C11H13NO3 and molecular weight is 207.23. What's more, its systematic name is N-Acetyl-D-phenylalanine. This chemical should be sealed and stored in a cool and dry place. It is a kind of chiral chemical raw material and it is used as pharmaceutical intermediates. It is also used in biochemical research.

Physical properties of N-Acetyl-D-phenylalanine are: (1)ACD/LogP: -1.022; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.27; (4)ACD/LogD (pH 7.4): -4.63; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 66.4 Å2; (13)Index of Refraction: 1.548; (14)Molar Refractivity: 54.848 cm3; (15)Molar Volume: 172.709 cm3; (16)Polarizability: 21.744×10-24cm3; (17)Surface Tension: 48.4 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 228.338 °C; (20)Enthalpy of Vaporization: 75.179 kJ/mol; (21)Boiling Point: 453.944 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H](NC(=O)C)Cc1ccccc1
(2)Std. InChI: InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m1/s1
(3)Std. InChIKey: CBQJSKKFNMDLON-SNVBAGLBSA-N 

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