(2R)-2-Methylpent-4-enoic acid
Chemical compound
From Wikipedia, the free encyclopedia
(2R)-2-Methylpent-4-enoic acid is an organic acid with the chemical formula C6H10O2. Other names for this molecule include (R)-2-methyl-4-pentenoic acid, (R)-(â)-2-methyl-4-pentenoic acid, and methylallylacetic acid.
-2-methylpent-4-enoic_acid.svg)
| |
| Names | |
|---|---|
| Preferred IUPAC name
(2R)-2-Methylpent-4-enoic acid | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| EC Number |
|
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C6H10O2 | |
| Molar mass | 114.144 g·molâ1 |
| Density | 0.946 g/cm3 |
| Melting point | 87â88 °C (189â190 °F; 360â361 K) |
| Vapor pressure | 0.237 Torr |
| Acidity (pKa) | 4.67 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Synthesis
(R)-2-Methylpent-4-enoic acid can be synthesized using a chiral auxiliary such an oxazolidinone derivative, popularized by David Evans. One route of synthesis consists of three steps:
- acylation of the oxazolidinone using triethylamine as a base, and DMAP as an acyl carrier catalyst
- addition of a pentene group via enolate addition using Sodium bis(trimethylsilyl)amide as a base and allyl iodide as the pentene donor
- and cleavage of the oxazolidinone by LiOH solution in hydrogen peroxide.[1] and sulfite to reduce the peroxide to the acid.
Uses
(R)-2-Methylpent-4-enoic acid can also be used in synthesis of other chiral compounds. For example, it has been used in the process of synthesizing the drug Sacubitril as a reagent for adding a chiral center to the molecule.[2]