4655-89-4

Basic information

• Product Name: 3,4-Dihydro-2,2-dimethyl-5-methoxy-8-acetyl-2H-1-benzopyran-7-ol
• Synonyms: (7-Hydroxy-5-methoxy-2,2-dimethylchroman-8-yl)(methyl) ketone;1-(3,4-Dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-8-yl)ethanone;3,4-Dihydro-2,2-dimethyl-5-methoxy-8-acetyl-2H-1-benzopyran-7-ol;Dihydroalloevodionol
• CAS NO: 4655-89-4
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 0
• Mol File: 4655-89-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-Dihydro-2,2-dimethyl-5-methoxy-8-acetyl-2H-1-benzopyran-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-2,2-dimethyl-5-methoxy-8-acetyl-2H-1-benzopyran-7-ol(4655-89-4)
• EPA Substance Registry System: 3,4-Dihydro-2,2-dimethyl-5-methoxy-8-acetyl-2H-1-benzopyran-7-ol(4655-89-4)

Safety Data

• Hazardous Substances Data: 4655-89-4(Hazardous Substances Data)

Upstream product

• 870-63-3 prenyl bromide 
• 7507-89-3 2,6-dihydroxy-4-methoxy-acetophenone 
• 32541-38-1 1-(5,7-dihydroxy-2,2-dimethyl-chroman-8-yl)-ethanone 
• 77-78-1 dimethyl sulfate 
• 77179-30-7 1-(2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)ethan-1-one 
• 107-30-2 chloromethyl methyl ether 
• 50386-17-9 3,4-Dihydro-7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran 
• 125116-28-1 Acetic acid 5-methoxy-2,2-dimethyl-chroman-7-yl ester 
• 78-79-5 isoprene 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 115-18-4 2-methyl-3-buten-2-ol 
• 64-19-7 acetic acid 
• 484-18-4 1-(7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-ethanone 
• 74-88-4 methyl iodide 

Downstream Products

• 50678-96-1 5-methoxy-2,2-dimethyl-8-phenyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-10-one 
• 68634-30-0 5-methoxy-8-(4-methoxy-phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-10-one 
• 135940-07-7 8-(3,4-Dimethoxy-phenyl)-5-methoxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-10-one 
• 88055-39-4 9-Hydroxy-8-(4'-methoxyphenyl)-5-methoxy-2,2-dimethyl-3,4-dihydro-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-one 
• 86978-01-0 4-Methoxy-benzoic acid 8-acetyl-5-methoxy-2,2-dimethyl-chroman-7-yl ester 
• 88055-41-8 9-Hydroxy-8-(3',4'-dimethoxyphenyl)-5-methoxy-2,2-dimethyl-3,4-dihydro-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-one 
• 484-18-4 1-(7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-ethanone 
• 85526-78-9 1-(7-hydroxy-5-methoxy-2,2-dimethyl-chroman-8-yl)-3-phenyl-propan-1-one 
• 86978-02-1 1-(7-Hydroxy-5-methoxy-2,2-dimethyl-chroman-8-yl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 143725-44-4 5-Methoxy-8-(4-methoxy-phenyl)-2,2-dimethyl-2H-pyrano[2,3-f]chromen-10-one 

Relevant articles and documents

Mallotojaponins B and C: Total Synthesis, Antiparasitic Evaluation, and Preliminary SAR Studies

(Chemical Equation Presented). The first total syntheses of mallotojaponin B and C as well as several analogues have been achieved. Biological evaluation of the synthesized compounds against Plasmodium falciparum and Trypanosoma brucei have also been carried out.

A facile synthesis of acetyl-hydroxy-2, 2-dimethylchromans and 2,2- dimethyl-2H-3,4-dihydropyranoflavanones - Dihydro mixtecacin, atalantoflavone dimethyl ether and racemoflavone dimethyl ether

Synthesis of acetyl-hydroxy-2, 2-dimethyl chromans by thermal-Fries rearrangement of acetoxy-2, 2-dimethylchromans has been described. The reaction of acetyl-hydroxy chromans (2, 4 and 6) with aryl aldehyde in the presence of aqueous ethanolic potassium h

Heterocycles: Part 7 - Synthesis of acetyl hydroxy-2,2-dimethylchromans

Synthesis of acetyl hydroxy-2,2-dimethylchromans by two methods namely photo-Fries rearrangement of acetoxy-2,2-dimethylchromans (UV light, 253.7 nm) and Friedel-Crafts acetylation of hydroxy-2,2-dimethylchromans with gl. acetic acid using AlCl3/POCl3 has been described.

Convenient Synthesis of Alloevodione, Alloevodionol and Franklinone

3,4-Dihydro-6-hydroxy-5,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran (5), obtained by nuclear prenylation of 2,6-dimethoxyquinol, on methylation followed by Friedel-Crafts acetylation gives 8-acetyl-3,4-dihydro-7-hydroxy-5,6-dimethoxy-2,2-dimethyl-2H-1-benzopyran (7).Dehydrogenation of 7 with DDQ followed by methylation affords alloevodione (9).Similar isoprenylation of 2,6-dihydroxy-4-methoxyacetophenone gives a mixture of dichroman (10) and the monochroman (11).Dehydrogenation of 10 and 11 furnishes franklinone (3) and alloevodionol (1) respectively.

ACID-CATALYZED CONDENSATION OF ISOPRENE AND 2-METHYLBUT-3-EN-2-OL WITH PHLOROACETOPHENONE, NEW SYNTHESIS OF ALLOEVODIONOL AND FRANKLINONE

The naturally occurring acetylchromenes, alloevodionol (1) and franklinone (2) have been synthesized by the nuclear isoprenylation of phloroacetophenone followed by the partial methylation and dehydrogenation of the chromans thus obtained.

Hoesch Reaction of 3,4-Dihydro-2,2-dimethyl-2H-1-benzopyrans

A reinvestigation of the Hoesch reaction of 3,4-dihydro-7-hydroxy- and 3,4-dihydro-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyrans (I and IV) with acetonitrile and hydrogen chloride reveals the formation of 6-acetyl (II) and 6,8-diacetyl (III) derivatives in the case of I, and 6-acetyl (V), 8-acetyl (VI) and 6,8-diacetyl (VII) derivatives in the case of IV.However, when a similar reaction is carried out on benzopyrans VIII and XI only mono-acetyl derivatives are obtained in each case, i. e.IX and X from VIII, and XII and XIII from XI.