alpha-Methylene-gamma-butyrolactone

Base Information

• Chemical Name: alpha-Methylene-gamma-butyrolactone
• CAS No.: 547-65-9
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 29349990
• European Community (EC) Number: 208-931-6
• NSC Number: 205367
• UNII: 362Y256BOL
• DSSTox Substance ID: DTXSID2074663
• Nikkaji Number: J100.706H
• Wikipedia: Tulipalin_A
• Wikidata: Q18882035
• Metabolomics Workbench ID: 66880
• ChEMBL ID: CHEMBL275748
• Mol file: 547-65-9.mol

Synonyms:alpha-methylene gamma-butyrolactone;alpha-methylene-gamma-butyrolactone;tulipalin A

Chemical Property of alpha-Methylene-gamma-butyrolactone

Chemical Property:

• Appearance/Colour: clear colourless to light yellow or slightly pink
• Vapor Pressure: 0.264mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: n20/D 1.472(lit.)
• Boiling Point: 204.4 °C at 760 mmHg
• Flash Point: 83.6 °C
• PSA: 26.30000
• Density: 1.07 g/cm³
• LogP: 0.48950
• Storage Temp.: 2-8°C
• Solubility.: water: soluble(lit.)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 115

Purity/Quality:

99% ^*data from raw suppliers

α-Methylene-γ-butyrolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43-52/53-10
• Safety Statements: 23-36/37-61-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CCOC1=O
• Description: Tulipalin A is an unsubstituted -methylene-butyrolaetone eontained in the sap of tulips, Alstroemeria spp. (Peruvian lily) and Erythronium (dog tooth violet, fawn-lily). Tulipalin B seems to have a weak capacities to sensitize.
• Uses: Very reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest Allergen in the Liliaeeae family of plants to whieh speeies such as Tulip, Alstromeria, Erythronium dens canis and americanum belong. α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.

Technology Process of alpha-Methylene-gamma-butyrolactone

There total 72 articles about alpha-Methylene-gamma-butyrolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

methyl 4-hydroxy-2-methylenebutanoate (61541-20-6) → α-methylene-γ-butyrolactone (547-65-9)

Guidance literature:

With dmap; In ethanol; at 25 ℃; for 150h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.02.024

Reference yield: 91.0%

carbon monoxide (201230-82-2) + 3-Butyn-1-ol (927-74-2) → α-methylene-γ-butyrolactone (547-65-9)

Guidance literature:

With triphenylphosphine; tin(ll) chloride; palladium dichloride; In acetonitrile; at 75 ℃; for 4h; under 5171.5 Torr;

DOI:10.1021/ja00415a020

Reference yield: 91.0%

α-bromomethyl-γ-butene lactone (58588-90-2) → α-methylene-γ-butyrolactone (547-65-9) + 3-methyl-5H-furan-2-one (22122-36-7)

Guidance literature:

With glucose dehydrogenase; D-glucose; NCR; nicotinamide adenine dinucleotide; NADH; In dimethyl sulfoxide; at 30 ℃; for 24h; Enzymatic reaction;

DOI:10.1002/adsc.201500094

upstream raw materials:

α-hydroxymethyl-γ-butyrolactone

4-butanolide

formaldehyd

formic acid ethyl ester

Downstream raw materials:

7-benzyl-7-aza-2-oxaspiro<4.4>nonan-1-one

3-phenylsulfanylmethyl-dihydro-furan-2-one

2-(1-Benzyl-4,5-dihydro-1H-imidazol-2-yl)-3-(2-oxo-tetrahydro-furan-3-yl)-propionic acid ethyl ester

C₁₇H₁₆O₄S

Refernces

• 1、 Harmon,Hutchinson. "-". . p. 1293. Retrieved 1973.
• 2、 Kim, Chul-Sa,Datta, Probal Kanti,Hara, Tetsuro,Itoh, Eiji,Horiike, Michio. "Precursor of α-methylene-γ-butyrolactone involved in the insecticidal activity of thunberg spiraea, Spiraea thunbergii". . p. 152 - 154. Retrieved 1999.
• 3、 Zhou, Jiawen,Schmidt, Annette M.,Ritter, Helmut. "Bicomponent transparent polyester networks with shape memory effect". . p. 939 - 942. Retrieved 2010.
• 4、 Beller, Matthias,Ge, Yao,Jackstell, Ralf,Jiao, Haijun,Liu, Jiawang,Spannenberg, Anke,Yang, Ji,Ye, Fei. "Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones". supporting information. p. 21585 - 21590. Retrieved 2020/09/23.
• 5、 -. "MANUFACTURING METHOD OF α-METHYLENE-γ-BUTYROLACTONE". Paragraph 0047-0050. . Retrieved 2018/08/19.