1515-76-0 Usage
Chemical Properties
clear colorless to slightly yellow viscous liquid
Uses
1-Acetoxy-1,3-butadiene was used as diene in the following reactions:Diels-Alder reaction with ortho-carbazolequinones to yield benzocarbazolequinone.Diels-Alder reaction with diethyl ketovinylphosphonate, with and without Lewis acid assistance.Diels-Alder reaction with methyl acrylate to yield racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid. It was used for the reaction with dienophiles such as maleimides, a juglone, a butyne-1,4-dione and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate and during visible light photocatalysis. It was also used as reactant during intermolecular oxa-Pictet-Spengler cyclization.
General Description
1-Acetoxy-1,3-butadiene (1-ABD) can be generated by potassium or sodium acetate catalyzed reaction between crotonaldehyde and acetic anhydride. The product is a mixture of cis and trans forms, that has been confirmed by its physical properties and IR spectra. It is reported to be formed as a major product during the acetoxylation of 1,3-butadiene (BD) in gas-phase in the presence of Pd-KOAc (palladium-potassium acetate) catalyst. 1-ABD participates as 2Π or 4Π diene in cycloaddition reactions. Enantioselective Diels Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-ABD in the presence of molecular sieves (mesh size:4?) has been reported.
Safety Profile
Poison by inhalation. Moderatelytoxic by other routes. A skin irritant. Mutation datareported. When heated to decomposition it emits acridsmoke.
Purification Methods
The commercial sample is stabilised with 0.1% of p-tert-butylcatechol. If the material contains crotonaldehyde (by IR, used in its synthesis), it should be dissolved in Et2O, shaken with 40% aqueous sodium bisulfite, then 5% aqueous Na2CO3, water, dried (Na2SO4) and distilled several times in a vacuum through a Widmer [Helv Chim Acta 7 59 1924] (p 11) or Vigreux column (p 11) [Wicterle & Hudlicky Collect Czech Chem Commun 12 564 1947, Hagemeyer & Hull Ind Eng Chem 41 2920 1949]. [Beilstein 2 III 295.]
Check Digit Verification of cas no
The CAS Registry Mumber 1515-76-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,1 and 5 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1515-76:
(6*1)+(5*5)+(4*1)+(3*5)+(2*7)+(1*6)=70
70 % 10 = 0
So 1515-76-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+
1515-76-0Relevant articles and documents
Stereoselective Substituent Effects on Conrotatory Electrocyclic Reactions of Cyclobutenes
Kirmse, Wolfgang,Rondan, Nelson G.,Houk, K. N.
, p. 7989 - 7991 (1984)
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Danno,S. et al.
, p. 4809 - 4813 (1969)
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1 - - 1, 3 - Alkadiene acyloxy method (by machine translation)
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Paragraph 0025-0029, (2019/05/08)
- 1, 3 - Alkadiene 1 - acyloxy [to] a production method of a industrially useful. (1) Represented by the formula [a] α, β - unsaturated aldehyde reaction to produce the metal alkoxide [...] process is performed, the following formula (3) is reacted with a carboxylic acid anhydride [...] step - 1, 3 - alkadiene represented by the preparation of 1 - acyloxy. (In formula (1), R1 - R3 The, each independently hydrogen, an alkyl group or the like. )[Drawing] no (by machine translation)
METHOD FOR PRODUCING 1-ACYLOXY-1,3-BUTADIENE
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Paragraph 0023, (2018/09/11)
PROBLEM TO BE SOLVED: To provide a method for producing a 1-acyloxy-1,3-butadiene that can be performed only with a base of a catalytic amount even when a substrate has a boiling point less than 135°C. SOLUTION: A method for producing a 1-acyloxy-1,3-butadiene represented by formula (3) includes treating α,β-unsaturated aldehyde with carboxylic acid anhydride and a catalytic amount of 4-dialkylaminopyridine at a temperature less than 135°C, without requiring a base other than 4-dialkylaminopyridine (R1-R2 independently represent H, a C1-30 linear/branched alkyl; R3 is H, a C1-30 alkyl or a C2-30 alkenyl; R4 is a C1-20 alkyl; alkyl groups of R3 and R4 may be linear/branched, substituted/unsubstituted with halogen, and the alkenyl group may further contain one or more C=C bonds in the group and may be linear/branched, substituted/unsubstituted with halogen). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
The 'Mikami'-catalyst in enantioselective diels-alder reactions of juglone-based dienophiles with different 1-oxygenated dienes: An investigation on the substitution pattern dependent regioselectivity
B?se, Dietrich,Frey, Wolfgang,Pietruszka, J?rg
supporting information, p. 2524 - 2532 (2014/11/08)
A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.
