139016-16-3

Basic information

• Product Name: (+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan
• Synonyms: (+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan
• CAS NO: 139016-16-3
• Molecular Weight: 320.388
• Mol File: 139016-16-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan(139016-16-3)
• EPA Substance Registry System: (+/-)-trans-2-(4-methoxyphenyl)-2,3-dihydro-5-methoxy-3-methylnaphtho<1,2-b>furan(139016-16-3)

Safety Data

• Hazardous Substances Data: 139016-16-3(Hazardous Substances Data)

Upstream product

• 84-85-5 4-methoxynaphth-1-ol 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 4043-71-4 isosafrole 

Relevant articles and documents

Reactivity of naphthol towards nucleophiles in anodic oxidation

Reactivity of the anodic oxidation of 4-methoxy-1-naphthol 1 in the presence of nucleophiles has been investigated. The reaction with electron-rich alkenic nucleophiles such as 1-methoxy-4-propenylbenzene 2 and isosafrole 3 gave a very high yield, whereas the reaction with dihydropyran 4 and dihydrofuran 5 gave a moderate yield, but with ethyl vinyl ether 6 gave a very low yield of the substituted dihydronaphthofuran derivatives 7-10 and 12, respectively. Unexpectedly, the glycosyl derivative 11 was preferentially produced rather than naphthofuran 10 upon using 5 as a nucleophile. In addition, the dimers 15 and 16 were obtained in moderate yield without addition of nucleophile to 1. The mechanism of the oxidation reactions including the [3+2] and [5+2] cycloaddition were discussed.

Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols

We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible-light-activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.

Mechanistic Aspects and Synthetic Applications of the Electrochemical and Iodobenzene Bis(trifluoroacetate) Oxidative 1,3-Cycloadditions of Phenols and Electron-Rich Styrene Derivatives

Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative.The yield o