| Identification | More | [Name]
(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine | [CAS]
109838-85-9 | [Synonyms]
(2R)-(-)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISOPROPYLPYRAZINE
BISLACTIMETHER
(R)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISOPROPYLPYRAZINE
(R)-2,5-DIMETHOXY-3-ISOPROPYL-3,6-DIHYDROPYRAZINE
SCHOELLKOPF-HARTWIG-REAGENT
2R-(-)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazin
Pyrazine, 2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-, (2R)-(9CI)
(R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
(2R)-3,6-DIMETHOXY-2-(1-METHYLETHYL)-2,5-DIHYDROPYRAZINE
(2R)-(-)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISOPROPYLPYRAZINE, 98+%
(R)-2,5-DIHYDRO-3,6-DIMETHOXY-2-ISOPROPYLPIPERAZINE
zR{-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
(-)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
(2R)-2,5-Dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazine
(R)-Schollkopf Reagent
2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
(2R)-(-)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine (aka (R )-Schollkopf reagent)
| [Molecular Formula]
C9H16N2O2 | [MDL Number]
MFCD00040565 | [Molecular Weight]
184.24 | [MOL File]
109838-85-9.mol |
| Chemical Properties | Back Directory | [alpha ]
-102 º (c=1%, EtOH) | [density ]
1.028 g/mL at 20 °C(lit.)
| [Fp ]
85 °C | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in Chloroform and Ethanol | [form ]
Oil | [pka]
3.81±0.60(Predicted) | [color ]
Clear Colourless to Pale Yellow | [Optical Rotation]
[α]20/D 102±5°, c = 1% in ethanol | [Usage]
An inhibitor with antitumor activity. | [Boiling point ]
100-102°C (20 hPa) | [BRN ]
3542790 | [Stability:]
Moisture Sensitive | [InChI]
InChI=1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3/t8-/m1/s1 | [InChIKey]
FCFWEOGTZZPCTO-MRVPVSSYSA-N | [SMILES]
[C@H]1(C(C)C)N=C(OC)CN=C1OC | [CAS DataBase Reference]
109838-85-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
NA 1993 / PGIII | [WGK Germany ]
3
| [F ]
10 | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear Colourless Liquid | [Uses]
(R)-3-Isopropyl-2,5-dimethoxy-3,6-dihydropyrazineChiral auxiliary for the synthesis of α-amino acids. It is an inhibitor with antitumor activity. | [Uses]
An inhibitor with antitumor activity. | [Synthesis]
Step A: Preparation of (R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine: To a 2L round bottom flask was added (R)-3-isopropylpiperazine-2,5-dione (20.7 g, 133 mmol), trimethine oxonium tetrafluoroborate (49.0 g, 331 mmol), and dichloromethane (500 mL). The reaction mixture was stirred vigorously at room temperature and protected by nitrogen.After 18 h, the reaction mixture changed to a clarified solution and formed a very viscous yellow oil at the bottom of the flask. Trimethyloxonium tetrafluoroborate (19.6 g, 133 mmol) was added additionally and stirring was continued at room temperature.After 23 h, the reaction mixture was cooled in an ice bath and 200 g of ice and 100 mL of concentrated ammonium hydroxide solution (28%) were added slowly. Stirring was continued in the ice bath for 1 hr. The organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane (2 x 50 mL). The organic layers were combined, washed sequentially with saturated sodium bicarbonate solution (2 x 100 mL) and brine (100 mL), dried with anhydrous potassium carbonate, filtered through a pad of diatomaceous earth, and concentrated under reduced pressure to give 25.9 g of light brown oil. The crude product was purified by column chromatography (eluent: ether/pentane=1:4) to afford 17.464 g of the target compound (R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine as a colorless oil in 71.5% yield.1H NMR (400 MHz, CDCl3) δ 4.08-3.94 (m, 3H), 2.95 (s, 3H) , 2.87 (s, 3H), 2.30-2.18 (m, 1H), 1.04 (d, J=7.03Hz, 3H), 0.76 (d, J=6.64Hz, 3H). | [References]
[1] Organic Process Research and Development, 2005, vol. 9, # 2, p. 185 - 187
[2] Patent: US2006/264431, 2006, A1. Location in patent: Page/Page column 20-21
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 2, p. 157 - 166 |
|
|