133181-02-9

Basic information

• Product Name: 3-hydroxy-2-methylene-pentanoic acid methyl ester
• CAS NO: 133181-02-9
• Molecular Weight: 144.17
• Mol File: 133181-02-9.mol
• Article Data: 37

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-2-methylene-pentanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2-methylene-pentanoic acid methyl ester(133181-02-9)
• EPA Substance Registry System: 3-hydroxy-2-methylene-pentanoic acid methyl ester(133181-02-9)

Safety Data

• Hazardous Substances Data: 133181-02-9(Hazardous Substances Data)

Upstream product

• 123-38-6 propionaldehyde 
• 292638-85-8 acrylic acid methyl ester 
• 1316312-91-0 C₁₂H₂₀O₅ 
• 343853-41-8 Methyl 3-hydroxy-2-(nitromethyl)pentanoate 

Downstream Products

• 138622-07-8 methyl (5RS)-5-<(1SR)-1-hydroxypropyl>-3-phenyl-2-isoxazoline-5-carboxylate 
• 138622-07-8 methyl (5RS)-5-<(1RS)-1-hydroxypropyl>-3-phenyl-2-isoxazoline-5-carboxylate 
• 153996-36-2 Methyl (E)-2-<<(2,4,6-trimethylbenzoyl)oxy>methyl>-2-pentenoate 
• 153996-35-1 methyl (E)-2-<<(4-nitrobenzoyl)oxy>methyl>-2-pentenoate 
• 115205-32-8 3-(methoxycarbonyl)-5-methyl-bicyclo<4.3.0>nona-3,7-diene 
• 115226-75-0 methyl 6-(1-propenyl)bicyclo<2.2.1>hept-2-ene-6-carboxylate 
• 58683-59-3 dimethyl 3-methyl-4-(1-propenyl)-1-cyclohexene-1,4-dicarboxylate 
• 58683-59-3 dimethyl 3-methyl-4-(1-propenyl)-1-cyclohexene-1,4-dicarboxylate 
• 20795-51-1 1-phenylpentan-3-one 
• 210691-47-7 methyl 2-benzyl-3-oxo-pentanoate 
• 361576-47-8 methyl 2-[(4-hydroxyphenyl)methyl]-3-oxopentanoate 
• 144828-57-9 (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(2S)-1-oxo-2-ethyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one 
• 144901-31-5 (1R,2S,6R,7R,9S)-(+)-9-(tert-butyldiphenylsilyloxy)-6-<(1S,2S)-1-hydroxy-2-ethyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one 
• 173346-42-4 1-O-<2'-<<(triisopropylsilyl)oxy>methyl>-2'-penten-1'-yl>-3,4,6-tri-O-benzyl-β-D-glucopyranose 

Relevant articles and documents

Enantioselective allylic substitution of Morita-Baylis-Hillman adducts catalyzed by planar chiral [2.2]paracyclophane monophosphines

Planar chiral [2,2]cyclophane monophosphines are efficient catalyst in the reaction of Morita-Baylis-Hillman adducts with phthalimide. The corresponding allylic substituted products were afforded in high yields and in good to moderate ee.

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HIGH-PRESSURE INITIATED SYNTHESIS OF DOMINICALURES 1 AND 2 BY THE BAYLIS-HILLMAN METHOD

The dimerization of methyl acrylate to dimethyl α-methyleneglutarate by the action of tributylphosphine in the absence of a solvent was investigated.Methyl α-methylene-β-hydroxypentanoate was obtained with a moderate yield by the condensation of propionaldehyde with methyl acrylate catalyzed by triphenylphosphine or 1,4-diazabicyclooctane and initiated by high pressure.In the last of these data a three-stage stereospecific synthesis of dominicalures 1 and 2 (components of the aggregation pheromone of the grain beetle) was realized from sec-amyl acrylate and propionaldehyde or isobutyraldehyde.

Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)

Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo

Highly efficient synthesis of novel Morita-Baylis-Hillman adducts from activated ketones using a DABCO-based hydroxy ionic liquid (HIL) as a recyclable catalyst-solvent

A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita-Baylis-Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita-Baylis-Hill

Hyphenating the curtius rearrangement with morita-baylis-hillman adducts: Synthesis of biologically active acyloins and vicinal aminoalcohols

Using Morita-Baylis-Hillman adducts as substrates, the Curtius rearrangement was performed in a sequence that allowed the synthesis of several hydroxy-ketones (acyloins) with great structural diversity and in good overall yields. These acyloins in turn were easily transformed into 1,2-anti aminoalcohols through a highly diastereoselective reductive amination step. The synthetic utility of these approaches was exemplified by performing the syntheses of (±)-bupropion, a drug used to treat the abstinence syndrome of smoker and (±)-spisulosine, a potent anti-tumoral compound originally isolated form a marine source.