(R)-2-氨基-2-甲基-4-戊烯酸 | 96886-55-4
中文名称:
(R)-2-氨基-2-甲基-4-戊烯酸
英文名称:
(2S)-2-amino-2-methyl-pent-4-enoic acid
CAS No.:
96886-55-4
分子式:
C6 H1 1 NO2
分子量:
129.157041788101
名称和标识符
MDL
MFCD00145248
InChIKey
QMBTZYHBJFPEJB-LURJTMIESA-N
Inchi
1S/C6H11NO2/c1-3-4-6(2,7)5(8)9/h3H,1,4,7H2,2H3,(H,8,9)/t6-/m0/s1
SMILES
[C@](N)(C)(C(=O)O)CC=C
别名信息
- 中文别名 -
(R)-2-氨基-2-甲基-4-戊烯酸
D-alpha-烯丙基丙氨酸
S-2-氨基-2-甲基-4-戊烯酸
(S)-(-)-α-烯丙基丙氨酸
(S)-2-氨基-2-甲基-4-戊烯酸
- 英文别名 -
(S)-2-Amino-2-methylpent-4-enoic acid
D-alpha-Allylalanine
(S)-(-)-2-Amino-2-methyl-4-pentenoic acid
(2S)-2-amino-2-methylpent-4-enoic acid
(S)- 2-(2'-PROPYLENYL) ALANINE
(S)-2-amino-2-methyl-4-pentenoic acid
4-Pentenoic acid, 2-amino-2-methyl-, (2S)-
alpha-methyl-L-Allylglycine
H-alpha-All-D-Ala-OH
(R)-2-Amino-2-methyl-4-pentenoic acid
(S)-(-)-α-Allylalanine
(2S)-2-Amino-2-methyl-4-pentenoic acid (ACI)
4-Pentenoic acid, 2-amino-2-methyl-, (S)- (ZCI)
(S)-α-Allylalanine
(2S)-2-amino-2-methyl-pent-4-enoic acid
物化性质
实验特性
LogP
1.06480
PSA
63.32000
水溶性
Very soluble in water.
熔点
285℃
计算特性
精确分子量
129.07900
氢键供体数量
2
氢键受体数量
3
可旋转化学键数量
3
重原子数量
9
复杂度
133
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)
-2.1
互变异构体数量
无
表面电荷
0
合成路线
合成路线:1 步
参考文献:
A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst
Belokon, Y. N.;
Davies, R. G.;
North, M. ,
Tetrahedron Letters ,
2000 ,
41(37) ,
7245-7248
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Water
;
1 h, rt
1.2
Reagents:
Lithium hydroxide
Solvents:
Tetrahydrofuran
,
Water
;
6 h, rt
参考文献:
New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids
Abellan, Tomas;
Chinchilla, Rafael;
Galindo, Nuria;
Najera, Carmen;
Sansano, Jose M. ,
Journal of Heterocyclic Chemistry ,
2000 ,
37(3) ,
467-479
合成路线:1 步
1.1
Reagents:
Sodium hydroxide
Solvents:
Water
;
rt; rt → 0 °C
1.2
Reagents:
Bromine
;
0 °C; 0 °C; 0 °C → 75 °C; 4 h, 75 °C
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
neutralized
参考文献:
Microbial whole cell-catalyzed desymmetrization of prochiral malonamides: practical synthesis of enantioenriched functionalized carbamoylacetates and their application in the preparation of unusual α-amino acids
Zhang, Li-Bin;
Wang, De-Xian;
Wang, Mei-Xiang ,
Tetrahedron ,
2011 ,
67(31) ,
5604-5609
合成路线:1 步
1.1
Reagents:
Sodium hydroxide
Catalysts:
(S,S)-TADDOL
Solvents:
Toluene
1.2
-
参考文献:
Asymmetric PTC C-alkylation catalyzed by chiral derivatives of tartaric acid and aminophenols. Synthesis of (R)- and (S)-α-methyl amino acids
Belokon, Yuri N.;
Kochetkov, Konstantin A.;
Churkina, Tatiana D.;
Ikonnikov, Nikolai S.;
Chesnokov, Alexey A.; et al ,
Journal of Organic Chemistry ,
2000 ,
65(21) ,
7041-7048
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Methanol
1.2
-
参考文献:
Asymmetric synthesis of bis(α-methylamino acid) via a BPB-Ni(II)-Ala complex
Ye, Lingya;
Wu, Hongli;
Zhang, Xiaolong;
Zhou, Jiadong;
Cao, Fei; et al ,
Youji Huaxue ,
2009 ,
29(8) ,
1282-1286
合成路线:1 步
1.1
Catalysts:
Aminopeptidase
Solvents:
Water
参考文献:
Enzymic resolution of α,α-disubstituted α-amino acid esters and amides
Kaptein, Bernard;
Boesten, Wilhelmus H. J.;
Broxterman, Quirinus B.;
Peters, Piet J. H.;
Schoemaker, Hans E.; et al ,
Tetrahedron: Asymmetry ,
1993 ,
4(6) ,
1113-16
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
,
Water
Solvents:
Water
参考文献:
Preparation of optically pure α-methyl-α-amino acids via alkylation of the nickel(II) Schiff base of (R,S)-alanine with (S)-2-N-(N'-benzylprolyl)aminobenzaldehyde
Belokon, Y. N.;
Chernoglazova, N. I.;
Kochetkov, C. A.;
Garbalinskaya, N. S.;
Belikov, V. M. ,
Journal of the Chemical Society ,
1985 ,
(1985) ,
171-2
合成路线:1 步
1.1
Reagents:
Amberlyst 15
Solvents:
Acetone
,
Water
;
16 h, pH 2 - 4, rt
1.2
Reagents:
Ammonia
Solvents:
Water
;
rt
参考文献:
Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones: asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid
Alonso, Francisco;
Davies, Stephen G.;
Elend, Almut S.;
Leech, Michael A.;
Roberts, Paul M.; et al ,
Organic & Biomolecular Chemistry ,
2009 ,
7(3) ,
527-536
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Acetic acid
,
Toluene
1.2
Solvents:
Ethanol
1.3
Reagents:
Ammonia
Solvents:
Water
参考文献:
Asymmetric synthesis of α-methyl α-amino acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure
Najera, Carmen;
Abellan, Tomas;
Sansano, Jose M. ,
European Journal of Organic Chemistry ,
2000 ,
(15) ,
2809-2820
合成路线:1 步
参考文献:
Product subclass 7: 2-aminoalkanoic acids (α-amino acids)
Wolkenberg, S. E.;
Garbaccio, R. M. ,
Science of Synthesis ,
2006 ,
20 ,
385-482
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Water
参考文献:
General method for the asymmetric synthesis of α-amino acids via alkylation of the chiral nickel(II) Schiff base complexes of glycine and alanine
Belokon, Yu. N.;
Bakhmutov, V. I.;
Chernoglazova, N. I.;
Kochetkov, K. A.;
Vitt, S. V.; et al ,
Journal of the Chemical Society ,
1988 ,
(2) ,
305-12
合成路线:1 步
参考文献:
Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids
Broxterman, Quirinus B.;
Kaptein, Bernard;
Kamphuis, Johan;
Schoemaker, Hans E. ,
Journal of Organic Chemistry ,
1992 ,
57(23) ,
6286-94
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Ethanol
,
Water
参考文献:
Asymmetric synthesis of α-methyl amino acids via alkylation of glycine, alanine and phenylalanine in chiral nickel(II) complexes
Belokon, Yu. N.;
Chernoglazova, N. I.;
Bakhmutov, V. I.;
Garbalinskaya, N. S.;
Belikov, V. M. ,
Izvestiya Akademii Nauk SSSR ,
1987 ,
(12) ,
2798-804
合成路线:1 步
1.1
Reagents:
Sodium hydroxide
Solvents:
Methanol
,
Acetone
;
2 h, rt
1.2
Reagents:
Hydrochloric acid
Solvents:
Water
;
pH 3 - 4, rt → 0 °C
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
3 h, 92 °C
1.4
Reagents:
(±)-Propylene oxide
Solvents:
Ethanol
;
1 h, rt
参考文献:
Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids by Diastereoselective Alkylation of Camphor-Based Tricyclic Iminolactone
Xu, Peng-Fei;
Li, Shuo;
Lu, Ta-Jung;
Wu, Chen-Chang;
Fan, Botao; et al ,
Journal of Organic Chemistry ,
2006 ,
71(12) ,
4364-4373
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Methanol
参考文献:
Asymmetric synthesis of γ-unsaturated amino acids using chiral auxiliary
Ye, Ling-Ya;
Wu, Hong-Li;
Zhang, Xiao-Long;
Zhou, Jia-Dong;
Cao, Fei; et al ,
Yingyong Huaxue ,
2009 ,
26(3) ,
346-348
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Methanol
,
Water
;
> 1 min, 20 - 60 °C
参考文献:
Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries
Saghyan, Ashot S.;
Dadayan, Ani S.;
Dadayan, Slavik A.;
Mkrtchyan, Anna F.;
Geolchanyan, Arpine V.; et al ,
Tetrahedron: Asymmetry ,
2010 ,
21(24) ,
2956-2965
合成路线:1 步
1.1
Reagents:
Sodium hydroxide
Solvents:
Dimethylformamide
;
60 min, 45 - 50 °C
1.2
Reagents:
Acetic acid
Solvents:
Water
;
neutralized
1.3
Reagents:
Hydrochloric acid
Solvents:
Methanol
,
Water
;
50 °C
参考文献:
New chiral NiII complexes of Schiff's bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids
Saghiyan, Ashot S.;
Dadayan, Slavik A.;
Petrosyan, Satenik G.;
Manasyan, Luisa L.;
Geolchanyan, Arpine V.; et al ,
Tetrahedron: Asymmetry ,
2006 ,
17(3) ,
455-467
合成路线:1 步
1.1
Reagents:
Hydrochloric acid
Solvents:
Tetrahydrofuran
,
Water
1.2
Reagents:
Lithium hydroxide
Solvents:
Tetrahydrofuran
,
Water
参考文献:
Asymmetric synthesis of α-methyl α-amino acids by diastereoselective alkylation of optically active 6-isopropyl-3-methyl-2,3-dihydro-6H-1,4-oxazin-2-ones
Chinchilla, Rafael;
Falvello, Larry R.;
Galindo, Nuria;
Najera, Carmen ,
Angewandte Chemie ,
1997 ,
36(9) ,
995-997
合成路线:1 步
参考文献:
Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of α-Substituted α-Amino Acids
Frauer, Alexandra;
Mehlfuehrer, Michaela;
Thirring, Klaus;
Berner, Heinz ,
Journal of Organic Chemistry ,
1994 ,
59(15) ,
4215-22
合成路线:1 步
参考文献:
(S)-2-[N-(N'-benzylprolyl)amino]benzophenone (BPB) - a reagent for the synthesis of optically pure α-amino acids
Belokon, I. ,
Janssen Chimica Acta ,
1992 ,
10(2) ,
4-12
合成路线:1 步
1.1
Solvents:
1,4-Dioxane
,
Water
;
1 h, 100 °C
参考文献:
Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine
Hugelshofer, Cedric L.;
Mellem, Kevin T.;
Myers, Andrew G. ,
Organic Letters ,
2013 ,
15(12) ,
3134-3137
合成路线:1 步
1.1
Reagents:
Cesium hydroxide
Solvents:
Water
;
2 h, 70 °C
1.2
Reagents:
Hydrochloric acid
Solvents:
Water
;
rt
参考文献:
Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1S)-(+)-3-carene derived tricyclic iminolactone
Lu, Ta-Jung;
Lin, Cheng-Kun ,
Journal of Organic Chemistry ,
2011 ,
76(6) ,
1621-1633