151101-22-3

Basic information

• Product Name: 2-Butenoic acid, 4-(phenylmethoxy)-, methyl ester, (2E)-
• CAS NO: 151101-22-3
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 151101-22-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Butenoic acid, 4-(phenylmethoxy)-, methyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenoic acid, 4-(phenylmethoxy)-, methyl ester, (2E)-(151101-22-3)
• EPA Substance Registry System: 2-Butenoic acid, 4-(phenylmethoxy)-, methyl ester, (2E)-(151101-22-3)

Safety Data

• Hazardous Substances Data: 151101-22-3(Hazardous Substances Data)

Upstream product

• 1117-71-1 methyl-4-bromo-2-butenoate 
• 100-51-6 benzyl alcohol 
• 14593-43-2 benzyl allyl ether 
• 70677-94-0 1,4-di(benzyloxy)but-2,3-ene 
• 100-39-0 benzyl bromide 
• 5927-18-4 trimethyl phosphonoacetate 
• 60656-87-3 benzyloxyacetoaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 151101-28-9 3-benzyloxymethyl-[1,2,4]trioxolane 
• 23326-27-4 Methyl 2-butynoate 

Downstream Products

• 312923-86-7 (1R,3aR,5R,6S,7S,7aR,8S)-7-Benzyloxymethyl-8-methyl-3-methylene-1-trimethylsilanyloxy-octahydro-1,5-methano-indene-6-carboxylic acid methyl ester 
• 312923-88-9 ((1R,3aR,5S,6S,7R,7aR,8S)-7-Benzyloxymethyl-8-methyl-3-methylene-1-trimethylsilanyloxy-octahydro-1,5-methano-inden-6-yl)-methanol 
• 312923-84-5 (1R,3aR,5R,6S,7S,7aR,8S)-7-Benzyloxymethyl-1-hydroxy-8-methyl-3-methylene-octahydro-1,5-methano-indene-6-carboxylic acid methyl ester 
• 312923-82-3 (1R,2S,3S,4R,6S,8R)-3-Benzyloxymethyl-8-(1-chloromethyl-vinyl)-6-methyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester 
• 401479-97-8 (2R,3S)-4-Benzyloxy-2,3-bis-methoxymethoxy-butyric acid methyl ester 
• 103499-50-9 (3R,4S)-5-(benzyloxy)-3,4-bis<(methoxymethyl)oxy>pentan-2-one 
• 183787-13-5 (+/-)-(E,E)-2,3,4,9-tetrahydro-1-(4-oxo-2-butenyl)-2-[1-oxo-4-(phenylmethoxy)-2-butenyl]-1H-pyrido[3,4-b]indole 
• 86209-87-2 trans-4-benzyloxycrotonyl-chloride 

Relevant articles and documents

Phosphine-catalyzed isomerization - Addition of oxygen nucleophiles to 2-alkynoates

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Aza-cope rearrangement-Mannich cyclizations for the formation of complex tricyclic amines: Stereocontrolled total synthesis of (±)-gelsemine

A detailed examination of the use of aza-Cope rearrangement-Mannich cyclization sequences for assembling the azatricyclo[4.4.0.02,8] decane core of gelsemine is described. Iminium ions and N-acyloxyiminium ions derived from endo-oriented 1-methoxy- or 1-hydroxybicyclo[2.2.2]oct-5-enylamines do not undergo the first step of this sequence, cationic aza-Cope rearrangement, to form cis-hydroisoquinolinium ions. However, the analogous base-promoted oxy-aza-Cope rearrangement does take place to form cis-hydroisoquinolones containing functionality that allows iminium ions or N-acyloxyiminium ions to be generated regioselectively in a subsequent step. Mannich cyclization of cis-hydroisoquinolones prepared in this way efficiently assembles the azatricyclo[4.4.0.02,8]decane unit of gelsemine. Using a sequential base-promoted oxy-aza-Cope rearrangement/Mannich cyclization sequence, gram quantities of azatricyclo[4.4.0.02,8]decanone 18, a central intermediate in our total of (±)-gelsemine, were prepared from 3-methylanisole in 12 steps and 16% overall yield.

Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides

Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.