137688-21-2

Basic information

• Product Name: (S)-(-)-1,2-Epoxy-5-hexene, GC 99%
• Synonyms: (S)-(-)-1,2-Epoxy-5-hexene, GC 99%;(S)-(-)-1,2-Epoxy-5-hexene, GC 99+%;S-3-Butenyloxirane;(S)-2-(But-3-enyl)oxirane;(S)-2-(but-3-en-1-yl)oxirane;(2S)-2-but-3-enyloxirane
• CAS NO: 137688-21-2
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.143
• Mol File: 137688-21-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 120.0±0.0 °C(Predicted)
• Appearance: /
• Density: 0.892±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-(-)-1,2-Epoxy-5-hexene, GC 99%(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1,2-Epoxy-5-hexene, GC 99%(137688-21-2)
• EPA Substance Registry System: (S)-(-)-1,2-Epoxy-5-hexene, GC 99%(137688-21-2)

Safety Data

• Hazardous Substances Data: 137688-21-2(Hazardous Substances Data)

Usage

Uses

(S)-1,2-Epoxy-5-hexene is a hydrocarbon derivative, which can be used as a pharmaceutical intermediate for pharmaceutical synthesis and pharmaceutical experimental research.

Upstream product

• 10353-53-4 1,2-epoxy-5-hexene 
• 592-42-7 1,5-Hexadien 
• 1374009-33-2 (R)-1-chlorohex-5-en-2-ol 

Downstream Products

• 1242310-34-4 (S)-1-phenylhept-6-en-3-ol 
• 1268882-21-8 (1aS,5aS)-2-(4-oxy-pyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-2-hydroxy-1-phenyl-ethyl)-amide 
• 191666-22-5 (4R)-5-(3,4-dihydroxyphenyl)-γ-valerolactone 
• 1108192-01-3 (4S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone 
• 822-58-2 (1R,2R,5S)-bicyclo[3.1.0]hexan-2-ol 
• 1268881-20-4 (1aS,5aS)-2-(4-oxypyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethylpropyl)amide 

Relevant articles and documents

Total synthesis and anti-inflammatory bioactivity of (?)-majusculoic acid and its derivatives

The first total synthesis of marine natural product, (?)-majusculoic acid (1) and its seven analogs (9–15), was accomplished in three to ten steps with a yield of 3% to 28%. The strategy featured the application of the conformational controlled establishment of the trans-cyclopropane and stereochemical controlled bromo-olefination or olefination by Horner–Wadsworth–Emmons (HWE) reaction. The potential anti-inflammatory activity of the eight compounds (1 and 9–15) was evaluated by determining the nitric oxide (NO) production in the lipopolysaccharide (LPS)-induced mouse macrophages RAW264.7. (?)-Majusculoic acid (1), methyl majusculoate (9), and (1R,2R)-2-((3E,5Z)-6-bromonona-3,5-dien-1-yl)cyclopropane-1-carboxylic acid (12) showed significant effect with inhibition rates of 33.68%, 35.75%, and 43.01%, respectively. Moreover, they did not show cytotoxicity against RAW264.7 cells, indicating that they might be potential anti-inflammatory agents.

Bioproduction of chiral epoxyalkanes using styrene monooxygenase from rhodococcus sp. ST-10 (RhSMO)

We describe the enantioselective epoxidation of straight-chain aliphatic alkenes using a biocatalytic system containing styrene monooxygenase from Rhodococcus sp. ST-10 and alcohol dehydrogenase from Leifsonia sp. S749. The biocatalyzed enantiomeric epoxidation of 1-hexene to (S)-1,2-epoxyhexane (44.6 mM) using 2-propanol as the hydrogen donor was achieved under optimized conditions. The biocatalyst had broad substrate specificity for various aliphatic alkenes, including terminal, internal, unfunctionalized, and di- and tri-substituted alkenes. Here, we demonstrate that this biocatalytic system is suitable for the efficient production of enantioenriched (S)-epoxyalkanes.

Minimal fluorous tagging strategy that enables the synthesis of the complete stereoisomer library of SCH725674 macrolactones

Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags-one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14- pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra.