(S)-2-Amino-8-oxo-decanoic acid methyl ester

Base Information

• Chemical Name: (S)-2-Amino-8-oxo-decanoic acid methyl ester
• CAS No.: 635680-16-9
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.293
• DSSTox Substance ID: DTXSID60457258
• Nikkaji Number: J1.960.788G
• Wikidata: Q82280039
• Mol file: 635680-16-9.mol

Synonyms:635680-16-9;(S)-2-AMINO-8-OXO-DECANOIC ACID METHYL ESTER;METHYL (2S)-2-AMINO-8-OXODECANOATE;(S)-2-Amino-8-oxodecanoic Acid Methyl Ester;DTXSID60457258;(S)-2-Amino-8-oxo-decanoic acid,methyl ester

Chemical Property of (S)-2-Amino-8-oxo-decanoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.000232mmHg at 25°C
• Boiling Point: 325.3°C at 760 mmHg
• Flash Point: 123.6°C
• PSA: 69.39000
• Density: 1.002g/cm³
• LogP: 2.11660
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 215.15214353
• Heavy Atom Count: 15
• Complexity: 204

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-2-Amino-8-oxodecanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)CCCCCC(C(=O)OC)N
• Isomeric SMILES: CCC(=O)CCCCC[C@@H](C(=O)OC)N
• Uses: A biologically important constitutent of naturally occuring cyclic tetrapeptides, such as apicidins and 9,10-depoxy-chlamydocin

Technology Process of (S)-2-Amino-8-oxo-decanoic acid methyl ester

There total 5 articles about (S)-2-Amino-8-oxo-decanoic acid methyl ester 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: 87.0%

trans-2-[4-(2-ethyl-[1,3]dioxolan-2-yl)-pentyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (635680-09-0) → 2-amino-8-oxo-decanoic acid methyl ester (635680-16-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1055/s-2003-41073

Reference yield:

2-(5-bromopentyl)-2-ethyl-[1,3]-dioxolane (34956-85-9) → 2-amino-8-oxo-decanoic acid methyl ester (635680-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / LDA / tetrahydrofuran / 18 h / -78 - -50 °C

2: 63 percent / aq. HCl / tetrahydrofuran / 12 h / 0 °C

With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; 1: Schoellkopf alkylation;

DOI:10.1002/adsc.200600421

Reference yield:

8-bromo-octan-3-one (2146-62-5) → 2-amino-8-oxo-decanoic acid methyl ester (635680-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / p-TsOH / benzene / 18 h / 85 °C

2: 65 percent / LDA / tetrahydrofuran / 18 h / -78 - -50 °C

3: 63 percent / aq. HCl / tetrahydrofuran / 12 h / 0 °C

With hydrogenchloride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; benzene; 2: Schoellkopf alkylation;

DOI:10.1002/adsc.200600421

upstream raw materials:

trans-2-[4-(2-ethyl-[1,3]dioxolan-2-yl)-pentyl]-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

2-(5-bromopentyl)-2-ethyl-[1,3]-dioxolane

6-bromo-1-hexanenitrile

8-bromo-octan-3-one

Refernces

• 1、 Jones, Philip,Altamura, Sergio,De Francesco, Raffaele,Paz, Odalys Gonzalez,Kinzel, Olaf,Mesiti, Giuseppe,Monteagudo, Edith,Pescatore, Giovanna,Rowley, Michael,Verdirame, Maria,Steinkühler, Christian. "A novel series of potent and selective ketone histone deacetylase inhibitors with antitumor activity in vivo". . p. 2350 - 2353. Retrieved 2008/12/22.
• 2、 Kim, Sanghee,Kim, Eun-Young,Ko, Hyojin,Jung, Young Hoon. "Efficient Syntheses of Biologically Important (S)-2-Amino-8-oxodecanoic Acid (Aoda) and Homologues". . p. 2194 - 2198. Retrieved 2007/10/03.