(S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine

Base Information

• Chemical Name: (S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine
• CAS No.: 134870-62-5
• Molecular Formula: C11H20N2O2
• Molecular Weight: 212.29
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID30452159
• Nikkaji Number: J760.687G
• Wikidata: Q72464824
• Mol file: 134870-62-5.mol

Synonyms:134870-62-5;(S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine;(2S)-3,6-diethoxy-2-propan-2-yl-2,5-dihydropyrazine;Pyrazine, 3,6-diethoxy-2,5-dihydro-2-(1-methylethyl)-, (2S)-;(S)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine;(S)-2, 5-Dihydro-3, 6-diethoxy-2-isopropylpyrazine;SCHEMBL1770651;(2s)-3,6-diethoxy-2-(propan-2-yl)-2,5-dihydropyrazine;DTXSID30452159;HRAZLOIRFUQOPL-JTQLQIEISA-N;MFCD09908235;AKOS015838715;AC-5184;AS-31805;AM20090800;CS-0444952;EN300-243984;A850265;2,5-Diethoxy-3,6-dihydro-3alpha-isopropylpyrazine;(2S)-2,5-dihydro-3,6-diethoxy-2-isopropyl pyrazine;(S)-3,6-diethoxy-2-isopropyl-2,5-dihydro-pyrazine

Chemical Property of (S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine

Chemical Property:

• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.5
• Boiling Point: 282.036 °C at 760 mmHg
• PKA: 6.74±0.60(Predicted)
• Flash Point: 102.851 °C
• PSA: 43.18000
• Density: 1.061 g/cm³
• LogP: 0.76580
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 212.152477885
• Heavy Atom Count: 15
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

(S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=NC(C(=NC1)OCC)C(C)C
• Isomeric SMILES: CCOC1=N[C@H](C(=NC1)OCC)C(C)C

Technology Process of (S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine

There total 4 articles about (S)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine 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: 90.9%

triethyloxonium fluoroborate (368-39-8) + (2S)-isopropylpiperazine-3,6-dione (16944-60-8) → (3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine (134870-62-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 72h;

DOI:10.1021/jo001679s

Reference yield: 82.0%

ethyl 2,2,2-trichloroacetimidate (23213-96-9) + (2S)-isopropylpiperazine-3,6-dione (16944-60-8) → (3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine (134870-62-5)

Guidance literature:

With tetrafluoroboric acid diethyl ether; In diethyl ether; dichloromethane; for 168h; Ambient temperature;

Reference yield:

t-Boc-L-valine (13734-41-3) → (3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine (134870-62-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: isobutyl chloroformate; Et₃N / CH₂Cl₂

1.2: CH₂Cl₂

2.1: H₂O / 0.25 h / 150 °C / microwave irradiation

3.1: CH₂Cl₂ / 20 °C

With triethylamine; isobutyl chloroformate; In dichloromethane; water;

DOI:10.1016/j.tetlet.2006.05.013

upstream raw materials:

ethyl 2,2,2-trichloroacetimidate

(2S)-isopropylpiperazine-3,6-dione

triethyloxonium fluoroborate

t-Boc-L-valine

Downstream raw materials:

(2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

(2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

(2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-((benzyloxycarbonylamino)methyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

(S)-2-Amino-6-benzyloxy-hexanoic acid ethyl ester

Refernces

• 1、 Li, Xiaoyan,Yin, Wenyuan,Sarma, P.V.V. Srirama,Zhou, Hao,Jun Ma,Cook, James M.. "Synthesis of optically active ring-A substituted tryptophans as IDO inhibitors". . p. 8569 - 8573. Retrieved 2007/10/03.
• 2、 Groth, Ulrich,Schmeck, Carsten,Schoellkopf, Ulrich. "Asymmetric Synthesis via Heterocyclic Intermediates, L Trichloroacetimidates, II Asymmetric Synthesis of α-Amino Acid Benzyl Esters via the Bisbenzyl Bislactam Ether of cyclo(-L-Val-Gly-)". . p. 321 - 324. Retrieved 2007/10/02.