97731-02-7 (2-氟-D-苯基丙氨酸,(R)-2-Amino-3-(2-fluorophenyl)propanoic acid)

快速询单

结构式：

2-氟-D-苯基丙氨酸MOL文件

CAS号：

97731-02-7

中文名称：

2-氟-D-苯基丙氨酸

英文名称：

(R)-2-Amino-3-(2-fluorophenyl)propanoic acid

分子式：

C₉H₁₀FNO₂

分子量：

183.179605960846

简介：

(R)-2-Amino-3-(2-fluorophenyl)propanoic acid 是一种苯丙氨酸衍生物。

2-氟-D-苯基丙氨酸(97731-02-7)名称与标识符

名称

中文别名：

2-氟-D-苯基丙氨酸;2-氟-D-苯丙氨酸;D-2-氟苯丙氨酸;2-氟-D-苯基丙氨酸(对映体的总和);2-氟-D-苯基丙氨酸 D-2-F-Phe-OH;

英文别名：

(R)-2-Amino-3-(2-fluorophenyl)propanoic acid;o-Fluoro-D-phenylalanine;D-2-Fluorophe;3-(2-Fluoropheny)-D-alanine;2-Fluoro-D-phenylalanine;D-2-FLUOROPHENYLALANINE;D-2-F-Phe-OH;H-D-Phe(2-F)-OH;2-Fluoro-D-Phenylalanine (Sum of Enantiomers);2-FLUORO-D-PHE;(2R)-2-amino-3-(2-fluorophenyl)propanoic acid;(R)-2-Fluorophenylalanine Hydrochloride Salt;H-D-Phe(2-F)-OH.HCl;PubChem23304;(r)-o-fluorophenylalanine;D-2-Fluoro phenylalanine;VZ24655;AM83328;RTR-0;2-Fluoro-D-phenylalanine (ACI);D;AC-5822;PD196711;MFCD00066447;CS-W010744;(R)-2-Amino-3-(2-fluorophenyl)propanoicacid;122839-51-4;(R)-3-(2-fluorophenyl)-2-aminopropanoic acid;AS-14324;97731-02-7;CHEBI:155832;EN300-199908;J-004866;(2R)-2-azaniumyl-3-(2-fluorophenyl)propanoate;DTXSID90924286;AKOS016843018;HY-W010028;2-Fluoro-D-phenylalanine, 99+% (sum of enantiomers);SCHEMBL268942;

标识符

MDL：

MFCD00066447

InChIKey：

NYCRCTMDYITATC-MRVPVSSYSA-N

Inchi：

1S/C9H10FNO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

SMILES：

C(C1C=CC=CC=1F)[C@@H](N)C(=O)O

2-氟-D-苯基丙氨酸(97731-02-7)物化性质

实验特性

LogP : 2.28240
PSA : 63.32000
沸点 : 308.1±32.0 °C at 760 mmHg
熔点 : 242-252°C
闪点 : 140.1±25.1 °C
颜色与性状 : 白色粉末
溶解性 : 未确定
比旋光度 : 14 º (c=1% in H2O)
密度 : 1.293

计算特性

精确分子量 : 219.046
氢键供体数量 : 2
氢键受体数量 : 4
可旋转化学键数量 : 3
同位素质量 : 219.046
重原子数量 : 13
复杂度 : 187
同位素原子数量 : 0
确定原子立构中心数量 : 1
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : -1.3
互变异构体数量 : 无
表面电荷 : 0
拓扑分子极性表面积 : 63.3

2-氟-D-苯基丙氨酸(97731-02-7)安全信息

WGK Germany： 3
安全说明： S22;S24/25
危险品标志： Xi
危害声明：H315; H319; H335
警示性声明：P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501
储存条件： Store at room temperature
信号词： Warning

2-氟-D-苯基丙氨酸(97731-02-7)推荐厂家更多厂家(38)

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2-氟-D-苯基丙氨酸(97731-02-7)合成路线

合成路线：1 步

208655-11-2

_99%99%

97731-02-7

反应条件：

1.1 Reagents: Pyridoxal 5′-phosphate Catalysts: 2-Aminohexano-6-lactam racemase , D-Amino acid amidase Solvents: Water ; 8 h, pH 8, 40 °C

参考文献：

Enzymatic Synthesis of Chiral Phenylalanine Derivatives by a Dynamic Kinetic Resolution of Corresponding Amide and Nitrile Substrates with a Multi-Enzyme System

Yasukawa, Kazuyuki; et al, Advanced Synthesis & Catalysis, 2012, 354(17), 3327-3332

合成路线：1 步

2629-55-2

_52-95%95%52%

97731-02-7

反应条件：

1.1 Reagents: Oxygen Catalysts: L-Amino acid oxidase , Catalase Solvents: Water
1.1 Reagents: Ammonium hydroxide , Ammonia borane Catalysts: Phenylalanine ammonia-lyase , L-Amino acid dehydrogenase Solvents: Water ; 7 h, pH 9.6, 37 °C
1.2 Reagents: Sulfuric acid Solvents: Water ; acidified
1.1 Reagents: Ammonia borane Catalysts: L-Amino acid oxidase Solvents: Water ; 20 h, pH 8, 30 °C
1.2 Reagents: Perchloric acid Solvents: Water

参考文献：

Preparation of (R)-phenylalanine analogs by enantioselective destruction using L-amino acid oxidaseSynthesis of D- and L-Phenylalanine Derivatives by Phenylalanine Ammonia Lyases: A Multienzymatic Cascade ProcessDeracemization and Stereoinversion to Aromatic D-Amino Acid Derivatives with Ancestral L-Amino Acid Oxidase

Pirrung, Michael C.; et al Parmeggiani, Fabio; et al Nakano, Shogo ; et al, Journal of Organic Chemistry, 1993, 58(4), 957-8

合成路线：1 步

130835-03-9

80980-62-7

_90%90%

97731-02-7

反应条件：

1.1 Reagents: Zinc acetate Solvents: Methanol
1.2 Reagents: Hydrochloric acid

参考文献：

Asymmetric synthesis of fluorophenylalanines and (trifluoromethyl)phenylalanines; the use of chiral pyridoxamine-like pyridinophane-zinc complex as an enzyme mimic

Ando, Makoto; et al, Bulletin of the Chemical Society of Japan, 1990, 63(7), 1925-8

合成路线：1 步

1001855-71-5

_85%85%

97731-02-7

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 6 h, 40 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ; neutralized

参考文献：

Preparation of chiral halogenated phenylalanines from tertiary-butyl 2-diphenyliminoacetate using chiral spiro quaternary ammonium salt phase transfer catalysts

, Japan, , ,

合成路线：1 步

403500-24-3

97731-02-7

反应条件：

1.1 Catalysts: Dihydropyrimidinase Solvents: Dimethyl sulfoxide , Water ; 72 h, pH 9, 42 °C
1.2 Reagents: Sodium nitrite , Hydrochloric acid Solvents: Water ; 6 h, pH 2 - 3, 0 °C

参考文献：

Unnatural D-amino acids as building blocks of new peptidomimetics

Latacz, Gniewomir; et al, Acta Poloniae Pharmaceutica, 2006, 63(5), 430-433

合成路线：1 步

69078-49-5

97731-02-7

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water

参考文献：

Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans

Porter, John; et al, International Journal of Peptide & Protein Research, 1987, 30(1), 13-21

合成路线：1 步

97731-02-7

参考文献：

Fluorinated phenylalanines and their derivatives. 4. The receipt method of the enantiomers of isomeric fluorophenylalanines by resolution of their racematesAsymmetric synthesis of organoelement analogs of natural compounds. III. Biocatalytic method for the preparation of homochiral fluorine-substituted (R)- and (S)-phenylalanines and (S,R)- and (R,S)-phenylserinesA new method for the chemical-enzymic synthesis of optically pure L-amino acids from glycine

Kliukiene, R.; et al Soloshonok, V. A.; et al Belokon, Yu. N.; et al, Chemija, 1996, 19(4), 80-82

合成路线：2 步

145243-39-6

97731-02-7

反应条件：

1.1 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Oxygen Catalysts: L-Amino acid oxidase , Catalase Solvents: Water

参考文献：

Preparation of (R)-phenylalanine analogs by enantioselective destruction using L-amino acid oxidase

Pirrung, Michael C.; et al, Journal of Organic Chemistry, 1993, 58(4), 957-8

合成路线：2 步

39801-61-1

97731-02-7

反应条件：

1.1 Reagents: Sodium hydroxide , Carboxypeptidase A Solvents: Water
2.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water

参考文献：

Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans

Porter, John; et al, International Journal of Peptide & Protein Research, 1987, 30(1), 13-21

合成路线：2 步

403500-19-6

97731-02-7

反应条件：

1.1 Reagents: Phosphorus , Hydrogen iodide Solvents: Water ; 0.5 h, reflux
2.1 Catalysts: Dihydropyrimidinase Solvents: Dimethyl sulfoxide , Water ; 72 h, pH 9, 42 °C
2.2 Reagents: Sodium nitrite , Hydrochloric acid Solvents: Water ; 6 h, pH 2 - 3, 0 °C

参考文献：

Unnatural D-amino acids as building blocks of new peptidomimetics

Latacz, Gniewomir; et al, Acta Poloniae Pharmaceutica, 2006, 63(5), 430-433

合成路线：2 步

81477-94-3

446-48-0

97731-02-7

反应条件：

1.1 Reagents: Potassium hydroxide Catalysts: 4,4′-Spirobi[4H-dinaphth[2,1-c:1′,2′-e]azepinium], 1,1′,7,7′,9,9′,14,14′-octakis… Solvents: Toluene , Water ; rt → 0 °C; 24 h, 0 °C
2.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 6 h, 40 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water ; neutralized

参考文献：

Preparation of chiral halogenated phenylalanines from tertiary-butyl 2-diphenyliminoacetate using chiral spiro quaternary ammonium salt phase transfer catalysts

, Japan, , ,

合成路线：3 步

27532-96-3

1013-88-3

97731-02-7

反应条件：

1.1 Solvents: Dichloromethane ; 24 h, rt
2.1 Reagents: Potassium hydroxide Catalysts: 4,4′-Spirobi[4H-dinaphth[2,1-c:1′,2′-e]azepinium], 1,1′,7,7′,9,9′,14,14′-octakis… Solvents: Toluene , Water ; rt → 0 °C; 24 h, 0 °C
3.1 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 6 h, 40 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water ; neutralized

参考文献：

Preparation of chiral halogenated phenylalanines from tertiary-butyl 2-diphenyliminoacetate using chiral spiro quaternary ammonium salt phase transfer catalysts

, Japan, , ,

合成路线：3 步

2629-55-2

407-25-0

97731-02-7

反应条件：

1.1 Solvents: Trifluoroacetic acid
2.1 Reagents: Sodium hydroxide , Carboxypeptidase A Solvents: Water
3.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water

参考文献：

Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans

Porter, John; et al, International Journal of Peptide & Protein Research, 1987, 30(1), 13-21

合成路线：3 步

81167-39-7

446-48-0

97731-02-7

反应条件：

1.1 Reagents: Potassium hydroxide Catalysts: Benzyltriethylammonium chloride
2.1 Reagents: Hydrochloric acid Solvents: Water
3.1 Reagents: Oxygen Catalysts: L-Amino acid oxidase , Catalase Solvents: Water

参考文献：

Preparation of (R)-phenylalanine analogs by enantioselective destruction using L-amino acid oxidase

Pirrung, Michael C.; et al, Journal of Organic Chemistry, 1993, 58(4), 957-8

合成路线：3 步

461-72-3

446-52-6

97731-02-7

反应条件：

1.1 Reagents: Acetic acid , Sodium acetate Solvents: Water ; 5 h, reflux; overnight, rt
2.1 Reagents: Phosphorus , Hydrogen iodide Solvents: Water ; 0.5 h, reflux
3.1 Catalysts: Dihydropyrimidinase Solvents: Dimethyl sulfoxide , Water ; 72 h, pH 9, 42 °C
3.2 Reagents: Sodium nitrite , Hydrochloric acid Solvents: Water ; 6 h, pH 2 - 3, 0 °C

参考文献：

Unnatural D-amino acids as building blocks of new peptidomimetics

Latacz, Gniewomir; et al, Acta Poloniae Pharmaceutica, 2006, 63(5), 430-433

合成路线：4 步

380-69-8

97731-02-7

反应条件：

1.1 Reagents: Hydrogen bromide Solvents: Water
2.1 Solvents: Trifluoroacetic acid
3.1 Reagents: Sodium hydroxide , Carboxypeptidase A Solvents: Water
4.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water

参考文献：

Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans

Porter, John; et al, International Journal of Peptide & Protein Research, 1987, 30(1), 13-21

合成路线：5 步

1068-90-2

446-48-0

97731-02-7

反应条件：

1.1 Reagents: Sodium ethoxide Solvents: Ethanol
1.2 Solvents: Ethanol
2.1 Reagents: Hydrogen bromide Solvents: Water
3.1 Solvents: Trifluoroacetic acid
4.1 Reagents: Sodium hydroxide , Carboxypeptidase A Solvents: Water
5.1 Reagents: Sodium hydroxide Solvents: Ethanol , Water

参考文献：

Synthesis, resolution and characterization of ring substituted phenylalanines and tryptophans

Porter, John; et al, International Journal of Peptide & Protein Research, 1987, 30(1), 13-21

合成路线：1 步

2629-55-2

97731-02-7

19883-78-4

反应条件：

1.1 Reagents: N-[3-[[[(1S)-3′-Formyl-2′-hydroxy[1,1′-binaphthalen]-2-yl]oxy]methyl]phenyl]-N′-… Solvents: Dimethyl sulfoxide
1.1 Reagents: N-[3-[[(3′-Formyl-2′-hydroxy[1,1′-binaphthalen]-2-yl)oxy]methyl]phenyl]-N′-pheny… Solvents: Dimethyl sulfoxide

参考文献：

Deracemization of racemic amino acids using (R)- and (S)-alanine racemase chiral analogues as chiral convertersDeracemization of racemic amino acids using (R)- and (S)-alanine racemase chiral analogues as chiral converters

Paik, Man-Jeong; et al Paik, Man-Jeong; et al, Bulletin of the Korean Chemical Society, 2014, 35(7), 2186-2188

合成路线：1 步

反应条件：

1.1 Catalysts: 2-Methyl-N-(tri-1-pyrrolidinylphosphoranylidene)-2-propanamine Solvents: N-Methyl-2-pyrrolidone ; 2 d, 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 20 min, 25 °C
1.3 Reagents: Diisopropylethylamine
1.4 Reagents: Trifluoroacetic acid Solvents: Dichloromethane , Water ; 30 min, 25 °C

参考文献：

Antibacterials and/or modulators of biofilm formation and methods of using the same

, United States, , ,

合成路线：1 步

反应条件：

1.1 Catalysts: Racemase, alanine , Aminomutase, phenylalanine 2,3- Solvents: Water ; 20 h, pH 8.0, 31 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ; pH 10 - 12

参考文献：

Enhanced Conversion of Racemic α-Arylalanines to (R)-β-Arylalanines by Coupled Racemase/Aminomutase Catalysis

Cox, Brad M.; et al, Journal of Organic Chemistry, 2009, 74(18), 6953-6959

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