1275584-84-3

Basic information

• Product Name: (R)-6-benzyloxy-7-(2',3'-dihydroxy-3'-methylbutyl)-2,2-dimethylchroman-4-one
• Synonyms: (R)-6-benzyloxy-7-(2',3'-dihydroxy-3'-methylbutyl)-2,2-dimethylchroman-4-one
• CAS NO: 1275584-84-3
• Molecular Weight: 384.472
• Mol File: 1275584-84-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-6-benzyloxy-7-(2',3'-dihydroxy-3'-methylbutyl)-2,2-dimethylchroman-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-6-benzyloxy-7-(2',3'-dihydroxy-3'-methylbutyl)-2,2-dimethylchroman-4-one(1275584-84-3)
• EPA Substance Registry System: (R)-6-benzyloxy-7-(2',3'-dihydroxy-3'-methylbutyl)-2,2-dimethylchroman-4-one(1275584-84-3)

Safety Data

• Hazardous Substances Data: 1275584-84-3(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 131341-58-7 2,5'-dihydroxy acetophenone 
• 31366-85-5 6-hydroxy-2,2-dimethyl-chroman-4-one 
• 1275584-55-8 2,2-dimethyl-6-(2'-methylbut-3'-en-2'-yloxy)chroman-4-one 
• 1275584-60-5 2,2-dimethyl-6-(2'-methylbut-3'-yn-2'-yloxy)chroman-4-one 
• 1275584-83-2 6-benzyloxy-2,2-dimethyl-7-(3'-methylbut-2'-enyl)chroman-4-one 
• 1275584-57-0 6-hydroxy-2,2-dimethyl-7-(3'-methylbut-2'-enyl)chroman-4-one 
• 1275584-66-1 2,2-dimethyl-7-(3'-methylbut-2'-enyl)-4-(triisopropylsiloxy)-2H-chromen-6-ol 
• 1275584-65-0 (2,2-dimethyl-6-(2'-methylbut-3'-en-2'-yloxy)-2H-chromen-4-yloxy)triisopropylsilane 

Downstream Products

• 1275584-85-4 (S)-6-benzyloxy-7-((3',3'-dimethyloxiran-2'-yl)methyl)-2,2-dimethylchroman-4-one 

Relevant articles and documents

Regioselectivity of the Claisen rearrangement in meta-allyloxy aryl ketones: An experimental and computational study, and application in the synthesis of (R)-(-)-pestalotheola D

A study of the regioselectivity of the Claisen rearrangement of meta-allyloxy aryl ketones showed that the electron-withdrawing carbonyl group has a major influence and strongly directs rearrangement to the more hindered ortho position. However, when the ketone is part of a ring structure, its electronic effect can be negated by conversion into its triisopropylsilyl enol ether, which dramatically reverses the regiochemistry of the Claisen rearrangement. DFT calculations suggest that the effect is electronic although there is also a steric effect of the bulky silyl group. This strategy for influencing the regiochemical outcome of the Claisen rearrangement was then employed in a short synthesis of the furo[2,3-g]chromene, (-)-pestalotheola D, that confirms the absolute stereochemistry of the natural product. A new strategy for influencing the regiochemical outcome of the Claisen rearrangement was developed and employed in a short synthesis of furo[2,3-g]chromene, (-)-pestalotheola D (see scheme), which confirms the absolute stereochemistry of the natural product.