(2S)-5-Methoxyflavanone

Base Information

• Chemical Name: (2S)-5-Methoxyflavanone
• CAS No.: 123931-32-8
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.285
• Nikkaji Number: J652.275K
• Mol file: 123931-32-8.mol

Synonyms:(2S)-5-Methoxyflavanone;BIDD:ER0536

Chemical Property of (2S)-5-Methoxyflavanone

Chemical Property:

• Vapor Pressure: 8.28E-08mmHg at 25°C
• Boiling Point: 436.1°C at 760 mmHg
• Flash Point: 209.4°C
• PSA: 0.00000
• Density: 1.199g/cm³
• LogP: 0.00000
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 254.094294304
• Heavy Atom Count: 19
• Complexity: 322

Purity/Quality:

5-Methoxyflavanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC2=C1C(=O)CC(O2)C3=CC=CC=C3
• Isomeric SMILES: COC1=CC=CC2=C1C(=O)C[C@H](O2)C3=CC=CC=C3

Technology Process of (2S)-5-Methoxyflavanone

There total 12 articles about (2S)-5-Methoxyflavanone 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: 95.0%

2'-Hydroxy-6'-methoxychalcone (40524-67-2,42079-68-5) → 5-methoxyflavanone (55947-36-9,123931-32-8)

Guidance literature:

With piperidine; potassium hydroxide; In water; at 20 ℃; for 0.0333333h;

DOI:10.1080/00397911.2011.621096

Reference yield: 83.0%

(E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one (40524-67-2,42079-68-5) → 5-methoxyflavanone (55947-36-9,123931-32-8)

Guidance literature:

With cesium fluoride; In water; acetonitrile; at 80 ℃; for 2h;

DOI:10.1016/j.tetlet.2021.153480

Reference yield: 64.0%

5-methoxychroman-4-one (863309-86-8) + phenylboronic acid (98-80-6) → 5-methoxyflavanone (55947-36-9,123931-32-8)

Guidance literature:

5-methoxychroman-4-one; With [2,2]bipyridinyl; palladium(II) trifluoroacetate; oxygen; In 1,4-dioxane; dimethyl sulfoxide; at 100 ℃;

phenylboronic acid; With oxygen; trifluoroacetic acid; In 1,4-dioxane; dimethyl sulfoxide; at 80 ℃;

DOI:10.1021/acs.joc.9b01162

upstream raw materials:

(E)-1-(2-hydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one

2'-hydroxy-6'-methoxyacetophenone

benzaldehyde

5-methoxyflavone

Downstream raw materials:

8-bromo-5-methoxy-2-phenyl-chromen-4-one

3,5-dihydroxy-2-phenyl-4H-chromen-4-one

5-methoxy-8-bromo-flavanone

Refernces

• 1、 Miura, Motofumi,Shigematsu, Karin,Toriyama, Masaharu,Motohashi, Shigeyasu. "Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride". supporting information. . Retrieved 2021/10/25.
• 2、 Cho, Yang Yil,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Nam Yong,Kim, Nam-Jung,Kim, Young Min,Lee, Soo Jin,Lee, Yong Sup,Park, Boyoung Y.,Son, Seung Hwan,Yoo, Hyung-Seok. "Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids". . p. 10012 - 10023. Retrieved 2019/08/30.