19041-15-7

Basic information

• Product Name: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE
• Synonyms: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE;(S)-GAMMA-VALEROLACTONE;(5S)-4-Hydroxypentanoic acid lactone;(5S)-5-Methyloxolan-2-one;(S)-5-Methyl-2-oxotetrahydrofuran;(S)-Dihydro-5-methyl-2(3H)-furanone;(S)-γ-Methyl-γ-butyrolactone;(S)-γ-Valerolactone
• CAS NO: 19041-15-7
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• Mol File: 19041-15-7.mol
• Article Data: 66

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• BRN: 3536337
• CAS DataBase Reference: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE(19041-15-7)
• EPA Substance Registry System: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE(19041-15-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 19041-15-7(Hazardous Substances Data)

Usage

General Description

(S)-gamma-methyl-gamma-butyrolactone is a chemical compound that belongs to the class of lactones, which are cyclic esters. It is a chiral compound, meaning it has a non-superimposable mirror image, and exists in two enantiomeric forms. This chemical has been researched for its potential as a precursor in the synthesis of pharmaceuticals and other organic compounds. It has also been studied for its potential pharmacological effects, such as its ability to act as a prodrug for GHB or its potential as a modulator of GABA receptor function. Additionally, (S)-gamma-methyl-gamma-butyrolactone has been investigated for its role in various chemical reactions and processes, making it a compound of interest in the fields of organic synthesis and drug discovery.

Upstream product

• 126252-14-0 (+/-)-γ-hydroxy-γ-methylbutyric acid methylester 
• 58879-33-7 (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone 
• 136801-92-8 [(S)-5-Methyl-dihydro-furan-(2E)-ylidene]-acetic acid methyl ester 
• 99631-16-0 ethyl (S)-4-hydroxypentanoate 
• 103712-16-9 methyl <2R,5S(S)>-5-<(4-acetoxy-1-oxopentyl)oxy>-2-methylhexanoate 
• 108-59-8 malonic acid dimethyl ester 
• 16088-62-3 (S)-Propylene oxide 
• 626-95-9 1,4-Pentanediol 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 124-38-9 carbon dioxide 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 92694-51-4 (S)-(+)-β-angelica lactone 
• 1219498-06-2 (S)-2-[(S)-4-hydroxypentanamide]-3-phenyl-N-[(R)-1-phenylethyl]propanamide 

Downstream Products

• 126187-54-0 (1S,2S)-2-methyl-(trans-2-phenylethenyl)cyclopropane 
• 126187-55-1 (1R,2S)-2-methyl-(trans-2-phenylethenyl)cyclopropane 
• 58927-89-2 S-6-phenyl-5-hexen-2-ol 
• 126110-35-8 R-trans-5-chloro-1-phenyl-1-hexene 
• 119326-50-0 (S)-2-[(S)-2-({(S)-2-[(E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoylamino]-propionyl}-methyl-amino)-3-(4-hydroxy-3-iodo-phenyl)-propionylamino]-propionic acid methyl ester 
• 119326-51-1 (S)-2-((S)-3-(4-Hydroxy-3-iodo-phenyl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-hydroxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-propionic acid methyl ester 
• 119326-52-2 (S)-2-((S)-3-(4-Hydroxy-3-iodo-phenyl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-hydroxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-propionic acid 
• 108675-63-4 geodiamolide A 
• 92998-79-3 (S)-(-)-α-(2-chlorobenzylidene)-γ-methyl-γ-butyrolactone 
• 681218-99-5 (S)-6-(triisopropylsiloxy)hept-2-en-1-yl para-toluenesulfonate 
• 18545-25-0 S-(-)-γ-methyl-(R/S)-γ-butyrolactol 
• 112775-67-4 (3RS,5S)-3-phenylseleno-5-methyldihydro-2(3H)-furanone 

Relevant articles and documents

Direct asymmetric reduction of levulinic acid to gamma-valerolactone: synthesis of a chiral platform molecule

Levulinic acid was directly converted to optically active (S)-gamma-valerolactone, a proposed biomass-based chiral platform molecule. By using a SEGPHOS ligand-modified ruthenium catalyst in methanol as a co-solvent, eventually, 100% chemoselectivity, and 82% enantioselectivity were achieved. The effect of the catalyst composition and reaction parameters on the activity and selectivity was investigated in detail. The conversion of a "real" biomass derived levulinic acid to optically active GVL without decreasing the enantioselectivity was also demonstrated.

Asymmetric Reduction of Chlorinated 4-Oxopentanoates with Bakers' Yeast. Synthesis of Optically Active γ-Butyrolactones and Useful Chiral Building Blocks

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The role of protic solvent in asymmetric hydrogenation of methyl levulinate in the presence of a ruthenium-containing catalyst

A comparative study of asymmetric hydrogenation and deuteration of methyl levulinate catalyzed by the RuII-(S)-BINAP-HCl system (BINAP is 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) in MeOH and MeOD was carried out. The results obtained suggest an important role of the protic solvent in the formation of catalytically active ruthenium complexes.

Access to lactone building blocks via horse liver alcohol dehydrogenase-catalyzed oxidative lactonization

The oxidative lactonization of 1,4-, 1,5-, and 1,6-diols using horse liver alcohol dehydrogenase (HLADH) is reported. Molecular oxygen was used as terminal electron acceptor by utilization of the laccase-mediator concept to regenerate the oxidized nicotinamide cofactor and producing water as sole byproduct. Spontaneous hydrolysis of the lactone products was identified as a major limiting factor toward preparative application of the system, which can be alleviated by using a two liquid phase approach to extracting the product into an organic solvent.

Stereoselective Reactions of Ester Enolates with Epoxides

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Kinetic resolution and chemoenzymatic dynamic kinetic resolution of functionalized γ-hydroxy amides

(Chemical Equation Presented) An efficient kinetic resolution of racemic γ-hydroxy amides 1 was performed via Pseudomas cepacia lipase (PS-C)-catalyzed transesterification. The enzyme PS-C tolerates both variation in the chain length and different functionalities giving good to high enantioselectivity (E values of up to >250). The combination of enzymatic kinetic resolution with a ruthenium-catalyzed racemization led to a dynamic kinetic resolution. The use of 2,4-dimethyl-3-pentanol as a hydrogen source to suppress ketone formation in the dynamic kinetic resolution yields the corresponding acetates in good yield and good to high enantioselectivity (ee's up to 98%). The synthetic utility of this procedure was illustrated by the practical synthesis of the versatile intermediate γ-lactone (R)-5-methyltetrahydrofuran-2-one.

Asymmetric hydrogenation of unsaturated carbonyl compounds catalyzed by BINAP-Ru(II) complexes. Enantioselective synthesis of γ-butyrolactones and cyclopentanones

Asymmetric hydrogenation of 2- and 4-alkylidene-γ-butyrolactones and 2-alkylidenecyclopentanones catalyzed by BINAP-Ru(II) complexes affords the corresponding γ-butyrolactones and cyclopentanones in 94-98% ee. Hydrogenation of (E)- and (Z)-2-propylidene-γ-butyrolactone catalyzed by the same catalyst gave the products with the same absolute configuration and in almost equal enantioselectivities, which shows that olefin geometry does not affect the stereochemistry and enantioselectivity.

Carboxyl Group-Directed Iridium-Catalyzed Enantioselective Hydrogenation of Aliphatic ?-Ketoacids

Although the transition metal-catalyzed asymmetric hydrogenation of aromatic ketones has been extensively explored, the enantioselective hydrogenation of aliphatic ketones remains a challenge because chiral catalysts cannot readily discriminate between the re and si faces of these ketones. Herein, we report a carboxyl-directing strategy for the asymmetric hydrogenation of aliphatic ?-ketoacids. With catalysis by iridium complexes bearing chiral spiro phosphino-oxazoline ligands, hydrogenation of aliphatic ?-ketoacids afforded chiral ?-hydroxylacids with high enantioselectivity (up to 99% ee). Mechanistic studies revealed that the carboxyl group of the substrate directs hydrogen transfer and ensures high enantioselectivity. Density functional theory calculations suggested the occurrence of chiral induction involving a hydrogen-hydrogen interaction between a hydride on the iridium atom and the substituent on the oxazoline ring of the ligand, and on the basis of the calculations, we proposed a catalytic cycle involving only Ir(III), which differs from the Ir(III)/Ir(V) catalytic cycle that operates in the hydrogenation of α,β-unsaturated carboxylic acids.

Chiron approach towards optically pure γ-valerolactone from alanine

A concise synthesis of both enantiomers of γ-valerolactone has been developed from commercially available Alanine. The key steps in the synthesis of these γ-Lactones are DIBAL-H reduction of ester (9) followed by in situ Wittig reaction with EtO2CCH = PPh3 ylide (13) (Z/E = 1: 3.5) and one pot lactonization triggered by deprotection of O-TBS ether (14).