(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate

• ChemBase ID: 150833
• Molecular Formular: C7H10O3
• Molecular Mass: 142.1525
• Monoisotopic Mass: 142.06299418
• SMILES: CC(=O)O[C@@H]1C[C@@H](C=C1)O
• Canonical SMILES: CC(=O)O[C@@H]1C[C@@H](C=C1)O
• InChI: InChI=1S/C7H10O3/c1-5(8)10-7-3-2-6(9)4-7/h2-3,6-7,9H,4H2,1H3/t6-,7+/m1/s1
• InChIKey: IJDYOKVVRXZCFD-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate
• IUPAC Traditional name: (1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate
• Synonyms: (1R,3S)-(+)-cis-4-Cyclopentene-1,3-diol 1-acetate; (1R,3S)-4-Cyclopentene-1,3-diol 1-acetate; (1R,4S)-cis-4-Hydroxy-2-cyclopentenyl acetate; (1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol; (1R,3S)-4-环戊烯-1,3-二醇-1-乙酸酯; (1R,3S)-(+)-顺式-4-环戊烯-1,3-二醇1-乙酸酯; (1R,4S)-顺式-4-羟基-2-环戊烯基乙酸酯; (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇

Database IDs

• CAS Number: 60410-16-4
• MDL Number: MFCD00078933
• Beilstein Number: 4663992
• PubChem SID: 24845089; 24868219; 162244993
• PubChem CID: 10154103

CALCULATED PROPERTIES

• Acid pKa: 14.793303
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.23236907
• LogD (pH = 7.4): -0.23236908
• Log P: -0.23236907
• Molar Refractivity: 36.2605 cm^3
• Polarizability: 14.079933 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 49-51 °C(lit.); 49-52 °C
• Optical Rotation: [α]20/D +68±2°, c = 2.3% in chloroform stab. with amylenes; [α]20/D +68°, c = 2.3 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, GC)
• Grade: puriss.
• Contains: 0.006% amylene as stabilizer
• Empirical Formula (Hill Notation): C7H10O3

DETAILS

Sigma Aldrich - 446041

Application
Building block for the synthesis of carbocyclic nucleosides and prostaglandins.1,2,3
Packaging
1 g in glass bottle

Sigma Aldrich - 00850

Other Notes
Use of derivatives in prostaglandin synthesis and other cyclopentanoid compounds 1; Pd-cat. substitution of the acetoxy group2