126566-41-4

Basic information

• Product Name: trans-4-t-Butoxy-5-hydroxy-2-cyclopenten-1-one
• Synonyms: trans-4-t-Butoxy-5-hydroxy-2-cyclopenten-1-one;(4S,5R)-4-tert-butoxy-5-hydroxycyclopent-2-en-1-one
• CAS NO: 126566-41-4
• Molecular Formula: C9H14O3
• Molecular Weight: 170.205660
• Mol File: 126566-41-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 288.81 °C at 760 mmHg
• Flash Point: 113.179 °C
• Appearance: /
• Density: 1.1 g/cm³
• Refractive Index: 1.492
• CAS DataBase Reference: trans-4-t-Butoxy-5-hydroxy-2-cyclopenten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-t-Butoxy-5-hydroxy-2-cyclopenten-1-one(126566-41-4)
• EPA Substance Registry System: trans-4-t-Butoxy-5-hydroxy-2-cyclopenten-1-one(126566-41-4)

Safety Data

• Hazardous Substances Data: 126566-41-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H14O3/c1-9(2,3)12-7-5-4-6(10)8(7)11/h4-5,7-8,11H,1-3H3/t7-,8-/m0/s1

Upstream product

• 62644-49-9 6-acetoxy-2H-pyran-3(6H)-one 
• 71443-31-7 6-t-butoxy-2,3-dihydro-6H-pyrano-3-one 
• 71443-22-6 1-O-benzoyl-2,3-dideoxy-D,L-pent-2-enopyranos-4-ulose 
• 35436-57-8 6-hydroxy-3,6-dihydro-2H-pyran-3-one 

Downstream Products

• 172296-00-3 (4S,5R)-4-t-butoxy-5-hydroxy-cyclopenten-1-one 
• 172296-00-3 (4R,5S)-4-t-butoxy-5-hydroxy-cyclopenten-1-one 
• 582-46-7 (+/-)-terrein 

Relevant articles and documents

Asymmetric synthesis of functionalised cyclopentenones via organocatalysed rearrangement and enzymatic resolution of pyranones

A direct asymmetric synthesis of a trans-4,5-difunctionalised cyclopentenone derivative has been achieved in 55% yield and 80% ee by organocatalysed rearrangement of a pyranone in tert-butanol by DABCO with simultaneous enzymatic resolution.

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 of functionalised cyclopentenones via rearrangement of pyranones

Substituted functionalised cyclopentenones could be obtained via base-mediated isomerisation of pyranones. (C) 2000 Elsevier Science Ltd.