2-Amino-2-(2-methylenecyclopropyl)acetic acid

Base Information

• Chemical Name: 2-Amino-2-(2-methylenecyclopropyl)acetic acid
• CAS No.: 2517-07-9
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.143
• Hs Code.: 2922499990
• Metabolomics Workbench ID: 70086
• Nikkaji Number: J540.699D
• Wikidata: Q105169556
• Mol file: 2517-07-9.mol

Synonyms:CPD-9757;MCPG;(2S,3S)-(Methylenecyclopropyl)glycine;2-amino-2-(2-methylenecyclopropyl)acetic acid;AC1NAMB5;2-amino-2-(2-methylidenecyclopropyl)acetic acid;SureCN1062833;2-(Methylencyclopropyl)-glycin;SCHEMBL1062833;CHEBI:165857;alpha-(Methylenecyclopropyl)glycine;AKOS006361483;C08292;(S)-2-AMINO-2-(2-METHYLENECYCLOPROPYL)ACETIC ACID

Chemical Property of 2-Amino-2-(2-methylenecyclopropyl)acetic acid

Chemical Property:

• Vapor Pressure: 0.00471mmHg at 25°C
• Melting Point: 246 °C (decomp)
• Boiling Point: 309°Cat760mmHg
• PKA: 2.18±0.10(Predicted)
• Flash Point: 140.7°C
• PSA: 49.33000
• Density: 1.18g/cm³
• LogP: 0.72760
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Water (Slightly)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 127.063328530
• Heavy Atom Count: 9
• Complexity: 164

Purity/Quality:

99%, ^*data from raw suppliers

α-(Methylenecyclopropyl)glycine(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=C1CC1C(C(=O)O)N
• Uses: α-(Methylenecyclopropyl)glycine, a homolog of Hypoglycine A (H998400), is an unusual amino acid found in Litchi chinensis seeds and is shown to have antimutagenic activity against spontaneous mutation of Salmonella typhimurium TA.

Technology Process of 2-Amino-2-(2-methylenecyclopropyl)acetic acid

There total 11 articles about 2-Amino-2-(2-methylenecyclopropyl)acetic 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: 38.0%

5-(2-methylenecyclopropyl)imidazolidine-2,4-dione (502150-92-7) → (2-methylenecyclopropyl)glycine (2517-07-9)

Guidance literature:

With barium dihydroxide; for 72h; Heating;

DOI:10.1055/s-2006-926320

Reference yield:

(2-hydroxymethyl)methylenecyclopropane (29279-66-1) → (2-methylenecyclopropyl)glycine (2517-07-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / (COCl)2; DMSO

2: 53 percent / aq. ethanol / 24 h / 58 - 60 °C

3: 38 percent / aq. Ba(OH)2 / 72 h / Heating

With barium dihydroxide; oxalyl dichloride; dimethyl sulfoxide; In ethanol; 1: Swern reaction / 2: Bucherer-Berg reaction;

DOI:10.1055/s-2006-926320

Reference yield:

2-methylenecyclopropane-1-carbaldehyde (142423-24-3) → (2-methylenecyclopropyl)glycine (2517-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / aq. ethanol / 24 h / 58 - 60 °C

2: 38 percent / aq. Ba(OH)2 / 72 h / Heating

With barium dihydroxide; In ethanol; 1: Bucherer-Berg reaction;

DOI:10.1055/s-2006-926320

upstream raw materials:

5-(2-methylenecyclopropyl)imidazolidine-2,4-dione

(2-hydroxymethyl)methylenecyclopropane

2-methylenecyclopropane-1-carbaldehyde

(S)-tert-Butoxycarbonylamino-((R)-2-methylene-cyclopropyl)-acetic acid methyl ester

Refernces

• 1、 Kurokawa, Natsuko,Ohfune, Yasufumi. "THE PALLADIUM(II)-ASSISTED SYNTHESES OF (+)-Α-(METHYLENECYCLOPROPYL) GLYCENE AND (+)-TRANS-α-(CARBOXYCYCLOPROPYL) GLYCINE, TWO BIOACTIVE AMINO ACIDS.". . p. 83 - 84. Retrieved 2007/10/02.