(S)-4-aminohex-5-enoic acid

Base Information

• Chemical Name: (S)-4-aminohex-5-enoic acid
• CAS No.: 74046-07-4
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.159
• European Community (EC) Number: 636-126-3
• UNII: 0S931RNJ68
• DSSTox Substance ID: DTXSID80224944
• Nikkaji Number: J323.106B
• Wikidata: Q27237189
• Mol file: 74046-07-4.mol

Synonyms:74046-07-4;(S)-4-aminohex-5-enoic acid;(S)-Vigabatrin;S-(+)-Vigabatrin;(S)-4-Amino-5-hexenoic Acid;(4S)-4-aminohex-5-enoic acid;S(+)-4-Aminohexenoic acid;(S)-4-Aminohex-5-enic acid;(S)-(+)-Vigabatrin;Vigabatrin, (S)-;(+)-gamma-Vinyl GABA;RMI 71890;S(+)-gamma-Vinyl GABA;S(+)-gamma-Vinyl-GABA;UNII-0S931RNJ68;0S931RNJ68;5-Hexenoic acid, 4-amino-, (+)-;S(+)-|A-Vigabatrin;4(S)-Amino-5-hexenoic Acid;MFCD00274076;(4S)-4-Amino-5-hexenoic Acid;S(+)--Vigabatrin;5-Hexenoic acid, 4-amino-, (4S)-;S(+)-gamma-Vigabatrin;(S)-4-aminohex-5-enoicacid;SCHEMBL465981;S(+)-gamma-Vigabatrin, solid;S(+)-| pound-VIGABATRIN;VIGABATRIN, S-(+)-;DTXSID80224944;PJDFLNIOAUIZSL-RXMQYKEDSA-N;(+)-.GAMMA.-VINYL GABA;BCP09861;5-Hexenoic acid,4-amino-, (4S)-;AKOS006275524;PD132087;4-aminohex-5-enoic acid/S(+)--VIGABATRIN;EN300-7258419;A898147;Q27237189

Chemical Property of (S)-4-aminohex-5-enoic acid

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 162-165 °C
• Boiling Point: 277.701°C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 121.749°C
• PSA: 63.32000
• Density: 1.064g/cm³
• LogP: 1.06480
• Storage Temp.: 2-8°C
• Solubility.: H2O: >20 mg/mL
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

97% ^*data from raw suppliers

(S)-Vigabatrin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC(CCC(=O)O)N
• Isomeric SMILES: C=C[C@H](CCC(=O)O)N
• Uses: Vigabatrin is a novel anti-epileptic drug. Antidepressant; antipsychotic; anxiolytic.

Technology Process of (S)-4-aminohex-5-enoic acid

There total 57 articles about (S)-4-aminohex-5-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: 96.0%

(5S)-5-ethenyl-2-pyrrolidinone (93288-23-4) → (+)-Vigabatrin (74046-07-4,68506-86-5)

Guidance literature:

With potassium hydroxide; In water; isopropyl alcohol; for 24h; Heating;

DOI:10.1016/S0040-4020(01)85629-5

Reference yield: 94.0%

methyl (-)-(4S)-4-[bis(tert-butoxycarbonyl)amino]hex-5-enoate (1099752-69-8) → (+)-Vigabatrin (74046-07-4,68506-86-5)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 60 ℃; for 12h;

DOI:10.1055/s-0028-1083158

Reference yield: 89.0%

(S)-ethyl 4--5-hexenoate (148073-34-1) → (+)-Vigabatrin (74046-07-4,68506-86-5) + (R)-vigabatrin (77162-51-7,68506-86-5)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; Yields of byproduct given. Title compound not separated from byproducts; a) 0 deg C, 4 h, b) room temperature, 8 h;

DOI:10.1021/jo00058a050

upstream raw materials:

(5S)-5-ethenyl-2-pyrrolidinone

(S)-(-)-5-ethenyl-1-butenyl-2-pyrrolidinone

(S)-5-ethenyl-1-butenyl-2-pyrrolidinone

(S)-ethyl 4--5-hexenoate

Downstream raw materials:

(-)-isoretronecanol

Refernces

• 1、 Karumanchi, Kishore,Kumar Natarajan, Senthil,Moturu, Krishna Murthy V. R.,Chavakula, Ramadas,Korupolu, Raghu Babu,Bonige, Kishore Babu. "Resolution of racemic Vigabatrin using tartaric acid". . p. 2221 - 2225. Retrieved 2018/07/21.
• 2、 Gnamm, Christian,Franck, Geraldine,Miller, Nicole,Stork, Timon,Broedner, Kerstin,Helmchen, Guenter. "Enantioselective iridium-catalyzed allylic aminations of allylic carbonates with functionalized side chains. Asymmetric total synthesis of (S)-vigabatrin". experimental part. p. 3331 - 3350. Retrieved 2009/05/27.