(R)-2-Amino-2-methylpent-4-enoic acid

Base Information

• Chemical Name: (R)-2-Amino-2-methylpent-4-enoic acid
• CAS No.: 96886-56-5
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2922498590
• European Community (EC) Number: 635-118-7
• DSSTox Substance ID: DTXSID00441959
• Nikkaji Number: J500.179J
• Mol file: 96886-56-5.mol

Synonyms:(R)-2-Amino-2-methylpent-4-enoic acid;96886-56-5;(R)-2-Amino-2-Methyl-4-Pentenoic Acid;(2R)-2-AMINO-2-METHYLPENT-4-ENOIC ACID;ALPHA-METHYL-D-ALLYLGLYCINE;A-ALLYL-L-ALA;ALPHA-ALLYL-D-ALA;alpha-allyl-l-alanine;(r)-alpha-allylalanine;SCHEMBL371079;DTXSID00441959;AC-060;LT0126;MFCD00153479;AKOS016843850;AB04108;|A inverted exclamation mark-Allyl-D-Ala;PS-12444;CS-0089885;A858663;(R)-(+)-alpha-Allylalanine, >=98.0% (HPLC);(R)-a-Allylalanine (>98%, >98%ee) (H-D-aMeGly(All)-OH)

Chemical Property of (R)-2-Amino-2-methylpent-4-enoic acid

Chemical Property:

• Vapor Pressure: 0.03mmHg at 25°C
• Melting Point: 296-299 °C
• Refractive Index: 1.484
• Boiling Point: 226.178 °C at 760 mmHg
• PKA: 2.26±0.10(Predicted)
• Flash Point: 90.59 °C
• PSA: 72.55000
• Density: 1.067 g/cm³
• LogP: 1.00050
• Storage Temp.: 2-8°C
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-α-Allylalanine ≥98.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC=C)(C(=O)O)N
• Isomeric SMILES: C[C@@](CC=C)(C(=O)O)N

Technology Process of (R)-2-Amino-2-methylpent-4-enoic acid

There total 27 articles about (R)-2-Amino-2-methylpent-4-enoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(2S,4R)-2-ferrocenyl-3-pivaloyl-4-allyl-4-methyl-1,3-oxazolidin-5-one → Cα-methyl-D-allylglycine (96886-56-5)

Guidance literature:

With amberlyst-15; In water; acetone; at 20 ℃; for 16h; pH=2 - 4;

DOI:10.1039/b814453b

Reference yield: 86.0%

(R)-4-allyl-2-(4-methoxyphenyl)-4-methyloxazol-5(4H)-one → Cα-methyl-D-allylglycine (96886-56-5)

Guidance literature:

(R)-4-allyl-2-(4-methoxyphenyl)-4-methyloxazol-5(4H)-one; With hydrogenchloride; In water; for 12h; Reflux;

With methyloxirane; In ethanol; for 0.5h; Reflux;

DOI:10.1021/jacs.5b10524

Reference yield: 81.0%

tert-butyl (1R,4R)-2'-methyl-2'-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylideneamino)pent-4'-enoate → (R,R)-camphor oxime (2792-42-9) + Cα-methyl-D-allylglycine (96886-56-5) + (S)-α-allylalanine (96886-55-4)

Guidance literature:

tert-butyl (1R,4R)-2'-methyl-2'-(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylideneamino)pent-4'-enoate; With sodium hydroxide; hydroxylamine hydrochloride; acetic acid; In methanol; at 20 ℃; for 72h;

With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(99)00581-5

upstream raw materials:

C^α-methyl-D,L-allylglycinamide

allyl bromide

rac-Ala-OH

L-alanin

Downstream raw materials:

(R)-2-((tert-butoxycarbonyl)amino)-2-methylpent-4-enoic acid

(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid

Refernces

• 1、 Saghyan, Ashot S.,Dadayan, Ani S.,Dadayan, Slavik A.,Mkrtchyan, Anna F.,Geolchanyan, Arpine V.,Manasyan, Luiza L.,Ajvazyan, Hrant R.,Khrustalev, Victor N.,Hambardzumyan, Hasmik H.,Maleev, Victor I.. "Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries". experimental part. p. 2956 - 2965. Retrieved 2011/03/19.
• 2、 Belokon', Yuri N.,Davies,Fuentes, Jose A.,North, Michael,Parsons, Teresa. "The influence of imine structure, catalyst structure and reaction conditions on the enantioselectivity of the alkylation of alanine methyl ester imines catalyzed by Cu(ch-salen)". . p. 8093 - 8096. Retrieved 2007/10/03.