69926-50-7

Basic information

• Product Name: (S,S)-5-CYCLOOCTENE-1,2-DIOL
• Synonyms: (S,S)-5-CYCLOOCTENE-1,2-DIOL
• CAS NO: 69926-50-7
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• Mol File: 69926-50-7.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S,S)-5-CYCLOOCTENE-1,2-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-5-CYCLOOCTENE-1,2-DIOL(69926-50-7)
• EPA Substance Registry System: (S,S)-5-CYCLOOCTENE-1,2-DIOL(69926-50-7)

Safety Data

• Hazardous Substances Data: 69926-50-7(Hazardous Substances Data)

Usage

General Description

(S,S)-5-CYCLOOCTENE-1,2-DIOL is a chemical compound with the molecular formula C8H14O2. It is a diol, meaning it contains two hydroxyl (OH) groups. (S,S)-5-CYCLOOCTENE-1,2-DIOL is also chiral, meaning it has a non-superimposable mirror image. (S,S)-5-CYCLOOCTENE-1,2-DIOL has potential applications in organic synthesis and as a chiral building block for the production of pharmaceuticals and agrochemicals. It is also used in the preparation of chiral auxiliaries and ligands and as a precursor for the synthesis of chiral amine derivatives. Additionally, it may have potential applications in the production of flavor and fragrance compounds.

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 5259-72-3 cyclo-octa-1,5-diene 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 
• 117468-08-3 (Z)-(1S,8R)-9-oxabicyclo[6.1.0]non-4-ene 
• 108-05-4 vinyl acetate 
• 31598-91-1 rac-(Z)-cyclooct-5-en-1,2-diol 

Downstream Products

• 4277-32-1 (1S,2S)-cyclooctane-1,2-diol 
• 917236-95-4 C₂₆H₃₀O₆ 
• 203319-31-7 (Z)-(1R,2R)-cyclooct-5-ene-1,2-diol 
• 51097-60-0 (Z)-oct-4-enedial 
• 119972-81-5 2-[(1R,2S,5R)-1-((Z)-(1R,8S)-8-Hydroxy-cyclooct-4-enyloxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone 

Relevant articles and documents

Micro-flow photosynthesis of new dienophiles for inverse-electron-demand Diels-Alder reactions. Potential applications for pretargeted in vivo PET imaging

Pretargeted PET imaging has emerged as an effective two-step in vivo approach that combines the superior affinity and selectivity of antibodies with the rapid pharmacokinetics and favorable dosimetry of smaller molecules radiolabeled with short-lived radionuclides. This approach can be based on the bioorthogonal inverse-electron-demand Diels-Alder (IEDDA) reaction between tetrazines and trans-cyclooctene (TCO) derivatives. We aimed to develop new [18F]TCO-dienophiles with high reactivity for IEDDA reactions, and favorable in vivo stability and pharmacokinetics. New dienophiles were synthesized using an innovative micro-flow photochemistry process, and their reaction kinetics with a tetrazine were determined. In vivo stability and biodistribution of the most promising 18F-radiolabeled-TCO-derivative ([18F]3) was investigated, and its potential for in vivo pretargeted PET imaging was assessed in tumor-bearing mice. We demonstrated that [18F]3 is a suitable dienophile for IEDDA reactions and for pretargeting applications.

Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4

A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

High-activity, single-site mesoporous WO3-MCF materials for the catalytic epoxidation of cycloocta-1,5-diene with aqueous hydrogen peroxide

For the first time, the high-activity, single-site mesoporous WO3-MCF materials were synthesized and characterized by N2 sorption, TEM, UV-vis DRS, UV-Raman, and XPS. It was found that the dispersion and nature of the tungsten species depend strongly on the tungsten oxide content and the support characteristic. The novel catalyst remains a highly ordered mesostructure of the silica support. The catalytic performance of the materials in the epoxidation of cycloocta-1,5-diene with aqueous H2O2 was investigated. The excellent catalytic performance of WO3-MCF in the selective oxidation of cycloocta-1,5-diene was attributed to the presence of isolated tetrahedral {WO4} species and the unique pore structure. The novel catalyst can be easily recycled after reaction and reused many times with no significant loss of activity. The good stability can be attributed to the presence of isolated tungsten species anchored on the support through W{single bond}O{single bond}Si covalent bonds.