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

Base Information

• Chemical Name: (R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine
• CAS No.: 110117-71-0
• Molecular Formula: C11H20N2O2
• Molecular Weight: 212.292
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50416071
• Nikkaji Number: J820.503E
• Wikidata: Q72464820
• Mol file: 110117-71-0.mol

Synonyms:110117-71-0;(R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine;(2R)-3,6-diethoxy-2-propan-2-yl-2,5-dihydropyrazine;(R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine;Pyrazine, 3,6-diethoxy-2,5-dihydro-2-(1-methylethyl)-, (2R)-;(2R)-3,6-Diethoxy-2-(propan-2-yl)-2,5-dihydropyrazine;4-chloro-5-amino-2-methylphenol;SCHEMBL2808933;DTXSID50416071;HRAZLOIRFUQOPL-SNVBAGLBSA-N;MFCD09836052;AKOS015838716;AKOS015900621;AC-24568;AS-47107;AM20090801;CS-0215544;EN300-258663;F12084;2,5-Diethoxy-6beta-isopropyl-3,6-dihydropyrazine;(r)-2,5-dihydro-3,6-diethoxy-5-isopropylpyrazine;(2R)-2-isopropyl-3,6-diethoxy-2,5-dihydropyrazine;(3R)-3-isopropyl-2,5-diethoxy-3,6-dihydropyrazine;(R)-3,6-Diethoxy-2-isopropyl-2,5-dihydro-pyrazine;Pyrazine, 2,5-dihydro-3,6-diethoxy-2-(1-methylethyl)-, (R)-;InChI=1/C11H20N2O2/c1-5-14-9-7-12-11(15-6-2)10(13-9)8(3)4/h8,10H,5-7H2,1-4H3/t10-/m1/s

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

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.00587mmHg at 25°C
• Refractive Index: 1.499
• Boiling Point: 282 °C at 760 mmHg
• PKA: 6.74±0.60(Predicted)
• Flash Point: 102.9 °C
• PSA: 43.18000
• Density: 1.06 g/cm³
• LogP: 0.76580
• 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

(R)-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
• Uses: (R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine is a useful intermediate for the preparation of Aliskiren, a new potent Renin inhibitor.

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

There total 9 articles about (R)-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: 92.0%

triethyloxonium fluoroborate (368-39-8) + (R)-3-(1-methylethyl)-piperazine-2,5-one (143673-66-9) → (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine (110117-71-0)

Guidance literature:

Reference yield: 92.0%

(R)-3-(1-methylethyl)-piperazine-2,5-one (143673-66-9) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine (110117-71-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1080/00397919508011464

Reference yield:

boron trifluoride diethyl etherate (109-63-7) + (2S)-isopropylpiperazine-3,6-dione (16944-60-8) → (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine (110117-71-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 48h;

upstream raw materials:

(R)-3-(1-methylethyl)-piperazine-2,5-one

epichlorohydrin

triethyloxonium fluoroborate

((R)-2-tert-butoxycarbonylamino-3-methylbutyrylamino)-acetic acid methyl ester

Downstream raw materials:

(2R,5R)-2-[2-(4-Benzyloxy-3-methoxy-phenyl)-ethyl]-3,6-diethoxy-5-isopropyl-2-methyl-2,5-dihydro-pyrazine

(2S,5R)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-3,6-diethoxy-5-isopropyl-2-prop-2-ynyl-2,5-dihydro-pyrazine

(2R,5R)-2-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-3,6-diethoxy-2-ethyl-5-isopropyl-2,5-dihydropyrazine

3-{(2S,5R)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl}-propan-1-ol

Refernces

• 1、 Handmann, Vera Iris,Merget, Markus,Tacke, Reinhold. "Sila-substitution of the α-amino acid proline: Synthesis of rac- and (R)-4,4-Dimethyl-4-sila-proline ethyl ester". . p. 133 - 138. Retrieved 2000.
• 2、 McGrath, Sally,Tortorici, Marcello,Drouin, Ludovic,Solanki, Savade,Vidler, Lewis,Westwood, Isaac,Gimeson, Peter,Van Montfort, Rob,Hoelder, Swen. "Structure-Enabled Discovery of a Stapled Peptide Inhibitor to Target the Oncogenic Transcriptional Repressor TLE1". supporting information. p. 9577 - 9584. Retrieved 2017/07/22.