22039-97-0

Basic information

• Product Name: (1-METHOXY-BUT-3-ENYL)-BENZENE
• Synonyms: (1-METHOXY-BUT-3-ENYL)-BENZENE;1-(1-methoxybut-3-enyl)benzene
• CAS NO: 22039-97-0
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.22826
• Mol File: 22039-97-0.mol
• Article Data: 72

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1-METHOXY-BUT-3-ENYL)-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-METHOXY-BUT-3-ENYL)-BENZENE(22039-97-0)
• EPA Substance Registry System: (1-METHOXY-BUT-3-ENYL)-BENZENE(22039-97-0)

Safety Data

• Hazardous Substances Data: 22039-97-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2808, 1984 DOI: 10.1021/jo00189a032Tetrahedron, 50, p. 871, 1994 DOI: 10.1016/S0040-4020(01)80802-4Tetrahedron Letters, 30, p. 2001, 1989 DOI: 10.1016/S0040-4039(00)99635-7

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 762-72-1 allyl-trimethyl-silane 
• 67-56-1 methanol 
• 18192-48-8 trimethyl(1-phenylbut-3-en-1-yl)silane 
• 538-86-3 benzyl methyl ether 
• 1825-61-2 Trimethylmethoxysilane 
• 100-52-7 benzaldehyde 
• 774-48-1 (diethoxymethyl)benzene 
• 2622-05-1 allylmagnesium bromide 
• 74-88-4 methyl iodide 
• 13865-07-1 (methoxy(phenylthio)methyl)benzene 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 149-73-5 trimethyl orthoformate 
• 591-50-4 iodobenzene 

Downstream Products

• 54322-72-4 (1-chlorobut-3-en-1-yl)benzene 
• 1214320-55-4 (Z)-triethyl(4-methoxy-4-phenylbut-1-enyl)silane 
• 1214320-68-9 (E)-triethyl(4-methoxy-4-phenylbut-1-enyl)silane 
• 1210067-10-9 (E)-4-methoxy-4-phenylbut-2-enyl propionate 
• 39551-05-8 4-methyl-N-(1-phenylbut-3-enyl)benzenesulfonamide 
• 865776-89-2 2-amino-5-(2-methoxy-2-phenyl-ethyl)-thiazole-4-carboxylic acid methyl ester 
• 865776-98-3 5-(2-methoxy-2-phenyl-ethyl)-thiazole-4-carboxylic acid methyl ester 
• 865777-07-7 5-(2-methoxy-2-phenyl-ethyl)-thiazole-4-carboxylic acid 
• 256229-09-1 3-methoxy-3-phenylpropanal 
• 3145-76-4 (2-methylcyclopropyl)benzene 
• 824-90-8 1-phenylbut-1-ene 
• 64275-34-9 1-phenyl-2-octene 
• 52117-33-6 4-methoxy-4-phenylbutan-2-one 

Relevant articles and documents

Evaluation of the relative magnitude of the β-effect of silicon and the γ-effect of tin by intermolecular competition

The relative magnitude of the β-effect of silicon and the γ-effect of tin was evaluated by intermolecular competition. An acetal was allowed to react with a 1:1 mixture of an allylsilane and a homoallylstannane in the presence of TMSOTf (trimethylsilyl trifluoromethanesulfonate); the former was found to be more reactive than does the latter, indicating that the β-silyl group activates the carbon-carbon double bond more effectively than the γ- stannyl group. This is consistent with the results of molecular-orbital calculations which indicate that the HOMO level of the allylsilane is higher than that of the homoallylstannane. The intermolecular competition between a homoallylstannane and a terminal alkene toward electrophilic reactions with an acetal have revealed that the former is more reactive than the latter. This result indicates that the stannyl group at the γ-position definitely activates the carbon-carbon double bond toward electrophiles.

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The Hosomi-Sakurai allylation in hexafluoroisopropanol: Solvent promotion effect

Hydrogen bond donating capacity of hexafluoroisopropanol was shown to be responsible for both the formation of its stoichiometric complexes with aldehydes and acetals and subsequent facilitation of their reactions with allylsilanes.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Multicatalytic Stereoselective Synthesis of Highly Substituted Alkenes by Sequential Isomerization/Cross-Coupling Reactions

Starting from readily available alkenyl methyl ethers, the stereoselective preparation of highly substituted alkenes by two complementary multicatalytic sequential isomerization/cross-coupling sequences is described. Both elementary steps of these sequences are challenging processes when considered independently. A cationic iridium catalyst was identified for the stereoselective isomerization of allyl methyl ethers and was found to be compatible with a nickel catalyst for the subsequent cross-coupling of the in situ generated methyl vinyl ethers with various Grignard reagents. The method is compatible with sensitive functional groups and a multitude of olefinic substitution patterns to deliver products with high control of the newly generated C=C bond. A highly enantioselective variant of this [Ir/Ni] sequence has been established using a chiral iridium precatalyst. A complementary [Pd/Ni] catalytic sequence has been optimized for alkenyl methyl ethers with a remote C=C bond. The final alkenes were isolated with a lower level of stereocontrol. Upon proper choice of the Grignard reagent, we demonstrated that C(sp2) - C(sp2) and C(sp2) - C(sp3) bonds can be constructed with both systems delivering products that would be difficult to access by conventional methods.

Highly efficient triphenyl(3-sulfopropyl)phosphonium functionalized phosphotungstic acid on silica as a solid acid catalyst for selective mono-allylation of acetals

Silica supported phosphotungstic acid functionalized with triphenyl(3-sulfopropyl)phosphonium (PW-Si/TPSP) was developed as a solid acid catalyst for C-C bond formation via Hosomi-Sakurai allylation of acetals. Functionalization of PW as well as its bindi