2-Methylidene-1,3,5-triphenylpentane-1,5-dione

Base Information

• Chemical Name: 2-Methylidene-1,3,5-triphenylpentane-1,5-dione
• CAS No.: 14045-45-5
• Molecular Formula: C24H20O2
• Molecular Weight: 340.422
• DSSTox Substance ID: DTXSID20395420
• ChEMBL ID: CHEMBL1505474
• Mol file: 14045-45-5.mol

Synonyms:2-methylidene-1,3,5-triphenylpentane-1,5-dione;14045-45-5;MLS000589466;SMR000212859;2-Methylene-1,3,5-triphenyl-pentane-1,5-dione;CHEMBL1505474;SCHEMBL21081852;BDBM54249;cid_3715215;DTXSID20395420;HMS2554C11;STL325420;AKOS022096482;2-methylene-1,3,5-triphenylpentane-1,5-dione;1,3,5-triphenyl-2-methylidene-1,5-pentanedione;2-methylidene-1,3,5-triphenyl-pentane-1,5-dione

Chemical Property of 2-Methylidene-1,3,5-triphenylpentane-1,5-dione

Chemical Property:

• PSA: 34.14000
• LogP: 5.48230
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 340.146329876
• Heavy Atom Count: 26
• Complexity: 488

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C(C(CC(=O)C1=CC=CC=C1)C2=CC=CC=C2)C(=O)C3=CC=CC=C3

Technology Process of 2-Methylidene-1,3,5-triphenylpentane-1,5-dione

There total 10 articles about 2-Methylidene-1,3,5-triphenylpentane-1,5-dione 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: 87.0%

3-phenylpropyne-1-ol + benzalacetophenone (94-41-7) → 2-methylidene-1,3,5-triphenylpentane-1,5-dione (14045-45-5)

Guidance literature:

With iron(III) trifluoromethanesulfonate; In 1,4-dioxane;

Reference yield:

benzaldehyde (100-52-7) → 2-methylidene-1,3,5-triphenylpentane-1,5-dione (14045-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 20 °C

2: bismuth(lll) trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / Sealed tube; Reflux

With bismuth(lll) trifluoromethanesulfonate; sodium hydroxide; In 1,2-dichloro-ethane; 1: |Aldol Condensation / 2: |Meyer-Schuster Rearrangement;

DOI:10.1021/acs.joc.1c02974

Reference yield:

acetophenone (98-86-2) → 2-methylidene-1,3,5-triphenylpentane-1,5-dione (14045-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 20 °C

2: bismuth(lll) trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / Sealed tube; Reflux

With bismuth(lll) trifluoromethanesulfonate; sodium hydroxide; In 1,2-dichloro-ethane; 1: |Aldol Condensation / 2: |Meyer-Schuster Rearrangement;

DOI:10.1021/acs.joc.1c02974

upstream raw materials:

benzalacetophenone

acetophenone

benzaldehyde

3-Phenyl-2-propyn-1-ol

Downstream raw materials:

2-(3-oxo-1,3-diphenylpropyl)-1-indanone

3-benzoyl-2,3-dihydro-4,6-diphenyl-4H-pyran

5-benzoyl-1,2,4-triphenylphosphorinane 1-oxide

5-benzoyl-1,2,4-triphenylphosphorinane 1-oxide