Ethanone,1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-

Base Information

• Chemical Name: Ethanone,1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-
• CAS No.: 24672-84-2
• Molecular Formula: C13H14 O3
• Molecular Weight: 218.252
• DSSTox Substance ID: DTXSID501206553
• Nikkaji Number: J459.214J
• Wikidata: Q103815864
• ChEMBL ID: CHEMBL2287247
• Mol file: 24672-84-2.mol

Synonyms:Ketone,5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl methyl (6CI,8CI);6-Acetyl-5-hydroxy-2,2-dimethyl-2H-chromene;6-Acetyl-5-hydroxy-2,2-dimethylchromene; Caleochromene A; Desmethylisoencecalin

Chemical Property of Ethanone,1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-

Chemical Property:

• Melting Point: 103 °C
• Boiling Point: 352.1±42.0 °C(Predicted)
• PSA: 46.53000
• Density: 1.154±0.06 g/cm3(Predicted)
• LogP: 2.77900
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 218.094294304
• Heavy Atom Count: 16
• Complexity: 319

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C2=C(C=C1)OC(C=C2)(C)C)O
• Uses: Caleochromene A is used in preparation of Pyranocoumarins. Also, used in preparation of Chromene derivatives which are used as HSP90 inhibitors,

Technology Process of Ethanone,1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-

There total 3 articles about Ethanone,1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)- 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: 57.4%

2',4'-dihydroxy-4-acetophenone (89-84-9) + dimethylacetal of 3-methyl-3-hydroxybutyraldehyde (31525-67-4) → 6-acetyl-7-hydroxy-2,2-dimethyl-1H-chromene (19013-03-7) + 6-acetyl-5-hydroxy-2,2-dimethylchromene (24672-84-2)

Guidance literature:

With pyridine; at 220 ℃; for 4h; Microwave irradiation;

DOI:10.1016/j.tetlet.2010.06.058

Reference yield: 51.0%

2',4'-dihydroxy-4-acetophenone (89-84-9) + 3,3-dimethyl acrylaldehyde (107-86-8) → 6-acetyl-7-hydroxy-2,2-dimethyl-1H-chromene (19013-03-7) + 6-acetyl-5-hydroxy-2,2-dimethylchromene (24672-84-2)

Guidance literature:

With pyridine; for 12h; Heating;

DOI:10.1016/S0031-9422(02)00475-2

Reference yield: 29.0%

3-chloro-3-methylbut-1-yne (1111-97-3) + 2',4'-dihydroxy-4-acetophenone (89-84-9) → 6-acetyl-5-hydroxy-2,2-dimethylchromene (24672-84-2) + 1-(2-hydroxy-4-((2-methylbut-3-yn-2-yl)oxy)phenyl)ethan-1-one (30414-96-1)

Guidance literature:

With copper(l) iodide; potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 65 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201701684

upstream raw materials:

2',4'-dihydroxy-4-acetophenone

3,3-dimethyl acrylaldehyde

dimethylacetal of 3-methyl-3-hydroxybutyraldehyde

3-chloro-3-methylbut-1-yne

Downstream raw materials:

glabrachromene II

(E)-3-(4-chlorophenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one

(2Z)-8,9-dihydro-2-(4-hydroxybenzylidene)-7,7-dimethyl-7H-furo[2,3-f]chromen-3(2H)-one

(E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one

Refernces

• 1、 Zhou, Ting,Shi, Qian,Lee, Kuo Hsing. "Anti-AIDS agents 83. Efficient microwave-assisted one-pot preparation of angular 2,2-dimethyl-2H-chromone containing compounds". experimental part. p. 4382 - 4386. Retrieved 2010/09/12.