3-Benzyl-5-(prop-2-yn-1-ylidene)oxolan-2-one

Base Information

• Chemical Name: 3-Benzyl-5-(prop-2-yn-1-ylidene)oxolan-2-one
• CAS No.: 103437-63-4
• Molecular Formula: C14H12O2
• Molecular Weight: 212.248
• DSSTox Substance ID: DTXSID90705678
• Mol file: 103437-63-4.mol

Synonyms:103437-63-4;3-Benzyl-5-(prop-2-yn-1-ylidene)oxolan-2-one;DTXSID90705678

Chemical Property of 3-Benzyl-5-(prop-2-yn-1-ylidene)oxolan-2-one

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 212.083729621
• Heavy Atom Count: 16
• Complexity: 339

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC=C1CC(C(=O)O1)CC2=CC=CC=C2

Technology Process of 3-Benzyl-5-(prop-2-yn-1-ylidene)oxolan-2-one

There total 5 articles about 3-Benzyl-5-(prop-2-yn-1-ylidene)oxolan-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: 31.0%

3-benzyl-5(E)-<3-(trimethylsilyl)prop-2-ynylidene>tetrahydro-2-furanone (103437-64-5) → 3-benzyl-5(E)-prop-2-ynylidenetetrahydro-2-furanone (103437-63-4)

Guidance literature:

With potassium cyanide; silver nitrate; In ethanol; water; at 0 ℃; for 0.5h; in the dark;

DOI:10.1021/ja00278a038

Reference yield:

3-benzyl-5(E)-(iodomethylene)tetrahydro-2-furanone (93040-53-0) + acetylene (74-86-2,25067-58-7) → 3-benzyl-5(E)-prop-2-ynylidenetetrahydro-2-furanone (103437-63-4)

Guidance literature:

With triethylamine; copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; at 35 ℃; Yield given;

DOI:10.1021/ja00334a068

Reference yield:

2-benzyl-4-pentynoic acid (96017-60-6) → 3-benzyl-5(E)-prop-2-ynylidenetetrahydro-2-furanone (103437-63-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 72.4 percent / N-iodosuccinimide, NaHCO₃, tetrabutylammonium hydroxide / CH₂Cl₂; H₂O / 0.5 h

2: 0.43 g / iodine / CH₂Cl₂ / 90 h / Ambient temperature; in the dark

3: PdCl₂(Ph₃P)2, CuI, Et₃N

4: 31 percent / AgNO₃, KCN / ethanol; H₂O / 0.5 h / 0 °C / in the dark

With potassium cyanide; bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; tetra(n-butyl)ammonium hydroxide; iodine; sodium hydrogencarbonate; silver nitrate; triethylamine; In ethanol; dichloromethane; water;

DOI:10.1021/ja00278a038

upstream raw materials:

3-benzyl-5(E)-<3-(trimethylsilyl)prop-2-ynylidene>tetrahydro-2-furanone

3-benzyl-5(E)-(iodomethylene)tetrahydro-2-furanone

acetylene

2-benzyl-4-pentynoic acid

Downstream raw materials:

methyl 2-benzyl-4,6-dioxoheptanoate