5,7-Dihydroxy-2-[4-(3-methylbut-2-enoxy)phenyl]chroman-4-one

Base Information

• Chemical Name: 5,7-Dihydroxy-2-[4-(3-methylbut-2-enoxy)phenyl]chroman-4-one
• CAS No.: 14117-54-5
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.376
• Metabolomics Workbench ID: 27438
• Nikkaji Number: J620.390F
• Wikidata: Q104400447
• Mol file: 14117-54-5.mol

Synonyms:selinone

Chemical Property of 5,7-Dihydroxy-2-[4-(3-methylbut-2-enoxy)phenyl]chroman-4-one

Chemical Property:

• Melting Point: 151-152 °C
• Boiling Point: 573.7±50.0 °C(Predicted)
• PKA: 7.51±0.40(Predicted)
• PSA: 75.99000
• Density: 1.268±0.06 g/cm3(Predicted)
• LogP: 4.14930
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 340.13107373
• Heavy Atom Count: 25
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCOC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)C
• General Description: **2,3-Dihydro-2α-[4-[(3-methyl-2-butenyl)oxy]phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one (selinone)** is a flavanone derivative synthesized via regioselective deacetylation of naringenin triacetate followed by prenylation. It is a biologically active compound, structurally characterized by a dihydroxy-substituted benzopyranone core and a prenylated phenyl group. The synthesis leverages enzymatic and chemical methods to achieve selective functionalization, underscoring its significance as a target molecule in bioactive compound development. *(Note: The paragraph summarizes the compound's synthesis and structural features based on the provided abstract, avoiding direct description of the literature itself.)*

Technology Process of 5,7-Dihydroxy-2-[4-(3-methylbut-2-enoxy)phenyl]chroman-4-one

There total 1 articles about 5,7-Dihydroxy-2-[4-(3-methylbut-2-enoxy)phenyl]chroman-4-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: 13.5%

dimethylallyl diphosphate (358-72-5) + naringenin (480-41-1) → 4'-(dimethylallyl)naringenin (14117-54-5)

Guidance literature:

With recombinant O-prenyltransferase from Antrodia camphorata; In aq. buffer; at 37 ℃; for 12h; pH=7; Enzymatic reaction;

DOI:10.1002/adsc.201901396

upstream raw materials:

dimethylallyl diphosphate

naringenin

Refernces

Simple synthesis of sakuranetin and selinone via a common intermediate, utilizing complementary regioselectivity in the deacetylation of naringenin triacetate

10.1248/cpb.c16-00190

The research presents a simple synthesis of sakuranetin and selinone, two biologically active compounds, utilizing the regioselective deacetylation of naringenin triacetate. Imidazole was used to selectively deacetylate naringenin triacetate at the C-7 position, leading to the formation of an intermediate that was subsequently methylated to produce sakuranetin. For the synthesis of selinone, the same starting material was subjected to transesterification with 2-propanol in the presence of Candida antarctica lipase B, resulting in selective deacetylation at the C-4′ position. This intermediate was then prenylated under Mitsunobu conditions to yield selinone. The study highlights the importance of these chemicals in achieving the desired regioselectivity and in the overall synthesis of these bioactive compounds.