172296-00-3

Basic information

• Product Name: TRANS-4-TERT-BUTOXY-5-HYDROXY- 2-CYCLOPE
• Synonyms: TRANS-4-TERT-BUTOXY-5-HYDROXY- 2-CYCLOPE;(4S,5R)-4-Tert-butoxy-5-hydroxycyclopent-2-enone
• CAS NO: 172296-00-3
• Molecular Formula: C9H14O3
• Molecular Weight: 170.21
• Mol File: 172296-00-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 52-54 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRANS-4-TERT-BUTOXY-5-HYDROXY- 2-CYCLOPE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-TERT-BUTOXY-5-HYDROXY- 2-CYCLOPE(172296-00-3)
• EPA Substance Registry System: TRANS-4-TERT-BUTOXY-5-HYDROXY- 2-CYCLOPE(172296-00-3)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 172296-00-3(Hazardous Substances Data)

Upstream product

• 71443-31-7 6-t-butoxy-2,3-dihydro-6H-pyrano-3-one 
• 62644-49-9 6-acetoxy-2H-pyran-3(6H)-one 
• 35436-57-8 6-hydroxy-3,6-dihydro-2H-pyran-3-one 
• 71443-22-6 1-O-benzoyl-2,3-dideoxy-D,L-pent-2-enopyranos-4-ulose 
• 108-05-4 vinyl acetate 
• 126566-41-4 trans-<4-(1,1-dimethylethoxy)-5-(hydroxy)>-2-cyclopenten-1-one 
• 98-00-0 (2-furyl)methyl alcohol 
• 19969-71-2 2,5-dimethoxy-2-hydroxymethyl-2,5-dihydrofuran 

Downstream Products

• 582-46-7 (+/-)-terrein 

Relevant articles and documents

Studies toward the synthesis of natural and unnatural dienediynes. Part 2: A practical approach to functionalised cyclopentenones

The dienediyne natural products contain a functionalised dihydroxylated cyclopentane motif. A critical evaluation of the methods for the preparation and rearrangements of pyranones to give 4,5-dihydroxylated cyclopentenones is presented. (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of trans-4,5-dioxygenated cyclopentenone derivatives by organocatalyzed rearrangement of pyranones and enzymatic dynamic kinetic resolution

Dioxygenated cyclopentenones are versatile building blocks for the synthesis of several natural products. Herein we report a direct asymmetric synthesis of trans-4,5-dioxygenated cyclopentenone derivatives through base-catalyzed rearrangement of pyranones followed by dynamic kinetic resolution. Milder conditions than previously reported for this rearrangement have been found regarding amine base catalysis, solvent and temperature effects. All data supports a mechanism involving cyclization of an intermediate formed by electrocyclic ring opening of a pyranone-derived enol. We have developed conditions for asymmetric synthesis of trans-4-tert-butoxy-5-hydroxycyclopent-2- enone, in 81% yield and 95% ee, and analogous dioxygenated cyclopentenones, via a lipase induced dynamic kinetic resolution.

Synthesis and melanin biosynthesis inhibitory activity of (±)-terrein produced by Penicillium sp. 20135

Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity. Terrein was isolated from Penicillium sp. 20135, prepared by a practical synthetic way, and evaluated first time for its melanin biosynthesis inhibitory activity.