4-Methoxy-3-buten-2-one

Base Information

• Chemical Name: 4-Methoxy-3-buten-2-one
• CAS No.: 51731-17-0
• Molecular Formula: C5H8 O2
• Molecular Weight: 100.117
• European Community (EC) Number: 225-087-4,257-364-0
• DSSTox Substance ID: DTXSID501308458
• Nikkaji Number: J149.912B,J284.587C
• Mol file: 51731-17-0.mol

Synonyms:4-Methoxy-3-buten-2-one;4652-27-1;4-Methoxybut-3-en-2-one;51731-17-0;(E)-4-methoxybut-3-en-2-one;trans-4-Methoxy-3-buten-2-one;(E)-4-Methoxy-3-buten-2-one;(3E)-4-Methoxy-3-buten-2-one;(3E)-4-Methoxybut-3-en-2-one;3-Buten-2-one, 4-methoxy-, (3E)-;EINECS 257-364-0;MFCD00008778;3-Buten-2-one, 4-methoxy-;1-methoxy-1-buten-3-one;EINECS 225-087-4;SCHEMBL560843;DTXSID501308458;(E)-4-methoxy-but-3-en-2-one;GEO-04315;(3E)-4-Methoxy-3-buten-2-one #;AKOS005259956;CS-W013712;CS-17363;EN300-53314;D78013;EN300-248251;F50213;4-METHOXY-3-BUTEN-2-ONE51731-17-0;A850060;J-515639;trans-4-Methoxy-3-buten-2-one, technical grade, 90%

Chemical Property of 4-Methoxy-3-buten-2-one

Chemical Property:

• Melting Point: 0℃
• Refractive Index: n20/D 1.468(lit.)
• Boiling Point: 200°Cat760mmHg
• Flash Point: 63.3°C
• PSA: 26.30000
• Density: 0.925g/cm³
• LogP: 0.73550
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 84.1

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-4-Methoxy-3-buten-2-one technical grade, 90% ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C=COC
• Isomeric SMILES: CC(=O)/C=C/OC

Technology Process of 4-Methoxy-3-buten-2-one

There total 9 articles about 4-Methoxy-3-buten-2-one 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: 86.0%

danishefsky's diene (54125-02-9) + (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (22323-80-4) → trans-4-methoxy-3-buten-2-one (51731-17-0) + (S)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-pyran-4(3H)-one (81277-29-4)

Guidance literature:

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde; With (1R,2S) Jacobsen's chromium catalyst; barium(II) oxide; In ethyl acetate; at 0 - 20 ℃; Inert atmosphere;

danishefsky's diene; In ethyl acetate; at 0 - 4 ℃; Darkness; Inert atmosphere;

With trifluoroacetic acid; In ethyl acetate; at 0 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol802942j

Reference yield:

danishefsky's diene (54125-02-9) + 3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → trans-4-methoxy-3-buten-2-one (51731-17-0) + (-)-(2S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-2H-pyran-4(3H)-one (250355-82-9) + (+)-(2R)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-2H-pyran-4(3H)-one (869336-43-6)

Guidance literature:

danishefsky's diene; 3-(tert-butyldiphenylsilyloxy)-1-propanal; With barium(II) oxide; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]]^(2-)-N,N',O,O'-manganese; In ethyl acetate; at 0 ℃; for 24h;

With trifluoroacetic acid; In dichloromethane; ethyl acetate; at 0 - 20 ℃; for 0.166667h; Title compound not separated from byproducts;

DOI:10.1039/b407240e

Reference yield:

C21H25N2(1+)*BF4(1-) + danishefsky's diene (54125-02-9) → (E)-5,5-bis(N-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-1-methoxy-1-penten-3-one + trans-4-methoxy-3-buten-2-one (51731-17-0)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1021/ja010890y

upstream raw materials:

2,5-dihydro-2H-2-oxothiophene

danishefsky's diene

3-oxobutyraldehyde

methanol

Downstream raw materials:

trans-6-Cyclohexyl-3-hexen-5-in-2-on

3-[2-isopropyl-5-methylcyclohexyloxy-(1R,2S,5R)]-3E-buten-2-one

methyl 2-acetoxy-4-methyl-3-nitrobenzoate

methyl 2-acetoxy-6-methyl-3-nitrobenzoate

Refernces

• 1、 Acocella, Maria Rosaria,Massa, Antonio,Palombi, Laura,Villano, Rosaria,Scettri, Arrigo. "Solvent-free Mukaiyama aldol reaction of O-silyl dienolates catalyzed by benzoic acid". . p. 6141 - 6144. Retrieved 2007/10/03.
• 2、 Mayr,Bug,Gotta,Hering,Irrgang,Janker,Kempf,Loos,Ofial,Remennikov,Schimmel. "Reference scales for the characterization of cationic electrophiles and neutral nucleophiles". . p. 9500 - 9512. Retrieved 2007/10/03.