1195113-83-7

Basic information

• Product Name: (R)-4-(3-hydroxybutyl)-4-hydroperoxy-2,5-cyclohexadien-1-one
• CAS NO: 1195113-83-7
• Molecular Weight: 198.219
• Mol File: 1195113-83-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-4-(3-hydroxybutyl)-4-hydroperoxy-2,5-cyclohexadien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(3-hydroxybutyl)-4-hydroperoxy-2,5-cyclohexadien-1-one(1195113-83-7)
• EPA Substance Registry System: (R)-4-(3-hydroxybutyl)-4-hydroperoxy-2,5-cyclohexadien-1-one(1195113-83-7)

Safety Data

• Hazardous Substances Data: 1195113-83-7(Hazardous Substances Data)

Upstream product

• 59092-94-3 (R)-rhododendrol 

Relevant articles and documents

Concise enantioselective synthesis of the ten-membered lactone cephalosporolide G and its C-3 epimer

A short and highly stereo-selective sequence for the first enantioselective total synthesis of the naturally occurring 10-membered lactone, which was obtained in only eight steps, was reported. The macrolactone ring was carried out by the use of a high-yielding pyridinium chlorochromate (PCC)-mediated oxidative cleavage of a bicyclic intermediate, generated in a domino sequence from a p-peroxyquinol. The synthesis was started with (-)-rhododendrol, which was obtained by enzymatic resolution of the racemic derivative. Phenol (R)-5 was submitted to an oxidative dearomatisation process with singlet oxygen, generated from Oxone in the presence of NaHCO3. The treatment of compound peroxyquinol with para-toluene sulfonic acid followed by Triton B gave, in one step and 49% yield, the tricyclic epoxide bicyclic derivative. A similar route was employed for the synthesis of the C-3 diastereoisomer of the natural product, which was obtained in only 7 steps and 15.2% overall yield.