Ethyl (2S)-2-acetamidonon-8-enoate

Base Information

• Chemical Name: Ethyl (2S)-2-acetamidonon-8-enoate
• CAS No.: 300831-20-3
• Molecular Formula: C13H23NO3
• DSSTox Substance ID: DTXSID30708229
• Wikidata: Q82642410
• Mol file: 300831-20-3.mol

Synonyms:Ethyl (2S)-2-acetamidonon-8-enoate;300831-20-3;8-Nonenoic acid, 2-(acetylamino)-, ethyl ester, (2S)-;SCHEMBL8148985;DTXSID30708229;KGONZHSGCSNOBH-LBPRGKRZSA-N;ethyl (s)-2-acetamido-8-nonenoate;(S)-ethyl 2-acetamido-8-nonenoate

Chemical Property of Ethyl (2S)-2-acetamidonon-8-enoate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 241.16779360
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCCCCC=C)NC(=O)C
• Isomeric SMILES: CCOC(=O)[C@H](CCCCCC=C)NC(=O)C

Technology Process of Ethyl (2S)-2-acetamidonon-8-enoate

There total 3 articles about Ethyl (2S)-2-acetamidonon-8-enoate 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:

ethyl (Z)-2-acetamido-2,8-nonadienoate (756894-33-4) → ethyl (S)-2-acetamido-8-nonenoate (300831-20-3)

Guidance literature:

With hydrogen; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In ethanol; for 18h; under 2327.17 Torr;

DOI:10.1021/ol0489907

Reference yield:

hept-6-enal (17206-61-0) → ethyl (S)-2-acetamido-8-nonenoate (300831-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / pyridine / 18 h / 20 °C

2: H₂ / [(COD)Rh((S,S)-Et-DUPHOS)]OTf / ethanol / 18 h / 2327.17 Torr

With hydrogen; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In pyridine; ethanol; 1: Perkin reaction;

DOI:10.1021/ol0489907

Reference yield:

7-octene-1,2-diol (85866-02-0) → ethyl (S)-2-acetamido-8-nonenoate (300831-20-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / NaIO₄ / H₂O / 1.5 h / 20 °C

2: 49 percent / pyridine / 18 h / 20 °C

3: H₂ / [(COD)Rh((S,S)-Et-DUPHOS)]OTf / ethanol / 18 h / 2327.17 Torr

With sodium periodate; hydrogen; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In pyridine; ethanol; water; 2: Perkin reaction;

DOI:10.1021/ol0489907

upstream raw materials:

ethyl (Z)-2-acetamido-2,8-nonadienoate

hept-6-enal

7-octene-1,2-diol

Downstream raw materials:

(S)-2-(tert-butoxycarbonylamino)non-8-enoic acid

C₃₀H₄₂BrN₃O₆

C₁₈H₃₁NO₅

ciluprevir