2-Acetamidonon-8-enoic acid

Base Information

• Chemical Name: 2-Acetamidonon-8-enoic acid
• CAS No.: 924309-93-3
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.277
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID60586517
• Mol file: 924309-93-3.mol

Synonyms:2-acetamidonon-8-enoic acid;924309-93-3;2-(acetylamino)non-8-enoic acid;(2R)-2-ACETAMIDONON-8-ENOIC ACID;924309-94-4;8-Nonenoic acid, 2-(acetylamino)-;8-Nonenoic acid, 2-(acetylamino)-, (2R)-;2-acetamidonon-8-enoicacid;2-Acetamido-8-Nonenoic Acid;SCHEMBL3777018;DTXSID60586517;CS-M1673;ZLB30993;AKOS015841061;MCULE-2926688484;SB75163;SB75164;CS-14442;DB-103734;VU0494737-1;F2145-0467

Chemical Property of 2-Acetamidonon-8-enoic acid

Chemical Property:

• PSA: 66.40000
• LogP: 2.10310
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 226

Purity/Quality:

≥95% ^*data from raw suppliers

2-Acetamidonon-8-enoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CCCCCC=C)C(=O)O

Technology Process of 2-Acetamidonon-8-enoic acid

There total 9 articles about 2-Acetamidonon-8-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: 99.0%

(R)-2-acetamido-8-nonenoic acid → (±)-2-acetamido-8-nonenoic acid (924309-93-3)

Guidance literature:

With acetic anhydride; In water; at 60 ℃; for 22h; Resolution of racemate; Inert atmosphere;

DOI:10.1021/op0601924

Reference yield: 45.0%

(±)-2-acetamido-8-nonenoic acid (924309-93-3) → (S)-2-amino-8-nonenoic acid (924307-76-6,1427467-46-6) + (R)-2-acetamido-8-nonenoic acid (924309-93-3)

Guidance literature:

With Acylase I; cobalt(II) chloride hexahydrate; sodium hydroxide; In water; at 20 - 38.5 ℃; for 7h; pH=7.5 - 7.8;

DOI:10.1021/op0601924

Reference yield:

7-bromo-hept-1-ene (4117-09-3) → (±)-2-acetamido-8-nonenoic acid (924309-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; caesium carbonate / acetonitrile / 24 h / Reflux

2.1: potassium hydroxide / ethanol / 2 h / Reflux

2.2: pH 4 - 5 / Reflux

3.1: citric acid / water / pH 4-5 / Reflux

With potassium carbonate; caesium carbonate; citric acid; potassium hydroxide; In ethanol; water; acetonitrile;

upstream raw materials:

7-chloro-1-heptene

7-bromo-hept-1-ene

Downstream raw materials:

(S)-2-amino-8-nonenoic acid

N-tert-butoxycarbonyl-2-amino-8-nonenoic acid dicyclohexylamine salt

Refernces

• 1、 Wang, Xiao-Jun,Zhang, Li,Smith-Keenan, Lana L.,Houpis, Ioannis N.,Farina, Vittorio. "Efficient synthesis of (S)-2-(cyclopentyloxycarbonyl)-amino-8-nonenoic acid: Key building block for BILN 2061, an HCV NS3 protease inhibitor". . p. 60 - 63. Retrieved 2012/12/26.