6690-12-6

Basic information

• Product Name: 9-oxabicyclo[6.1.0]non-2-ene
• Synonyms: 9-oxabicyclo[6.1.0]non-2-ene;1,2-Epoxy-7-cyclooctene;Einecs 229-734-1
• CAS NO: 6690-12-6
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18028
• EINECS: 229-734-1
• Mol File: 6690-12-6.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 178.1°Cat760mmHg
• Flash Point: 54.3°C
• Appearance: /
• Density: 0.993g/cm³
• Vapor Pressure: 1.36mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 9-oxabicyclo[6.1.0]non-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 9-oxabicyclo[6.1.0]non-2-ene(6690-12-6)
• EPA Substance Registry System: 9-oxabicyclo[6.1.0]non-2-ene(6690-12-6)

Safety Data

• Hazardous Substances Data: 6690-12-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12O/c1-2-4-6-8-7(9-8)5-3-1/h3,5,7-8H,1-2,4,6H2/b5-3-

Upstream product

• 186983-16-4 1,3-cyclooctadiene 
• 3806-59-5 1,3-cyclooctadiene 
• 1700-10-3 1,3-cyclooctadiene 

Downstream Products

• 121681-85-4 4-hydroxy-3-phenylthio-1-cyclooctene 
• 20642-83-5 9-oxa-bicyclo[4.2.1]-7-nonene 
• 23202-10-0 (Z)-cyclooct-2-enone 
• 4734-90-1 (Z)-3-cyclooctenone 
• 1580502-02-8 C₁₅H₁₇NO₅ 
• 4884-99-5 3-Methoxy-cyclooctanon-(2.4-dinitro-phenylhydrazon) 
• 108533-58-0 5-<(tert-butyldimethylsilyl)oxy>-3-(phenylsulfonyl)-1,3-cyclooctadiene 

Relevant articles and documents

A novel synthetic approach to the bicyclo[5.3.1]undecan-11-one framework of vinigrol

The first synthetic attempt commencing from an eight-membered ring to approach the [5.3.1] bicyclic core of vinigrol has demonstrated the feasibility of using the conformational bias of the cyclooctane-ring system to realize highly diastereoselective reactions. The synthetic potential of the newly disclosed access to in/out isomerism may stimulate broader interests. This journal is the Partner Organisations 2014.

MULTIPLE CYCLOADDITION REACTIONS FOR LABELING OF MOLECULES

The present invention relates to methods for linking tetrazines with dienophiles to establish at least two linkages by sequentially performing at least two cycloaddition reactions. The methods in particular allow establishing multi-labeling strategies. In particular, the invention relates to methods for forming linkages by cycloaddition reactions, wherein the method comprises reacting a first alkyl-substituted tetrazine with a first dienophile comprising a irans-cyclooctenyl group followed by reacting a second tetrazine with a second dienophile comprising a cyclooctynyl group, wherein the reaction of the first tetrazine with the first dienophile proceeds in the presence of the second dienophile.

Minimal tags for rapid dual-color live-cell labeling and super-resolution microscopy

The growing demands of advanced fluorescence and super-resolution microscopy benefit from the development of small and highly photostable fluorescent probes. Techniques developed to expand the genetic code permit the residue-specific encoding of unnatural amino acids (UAAs) armed with novel clickable chemical handles into proteins in living cells. Here we present the design of new UAAs bearing strained alkene side chains that have improved biocompatibility and stability for the attachment of tetrazine-functionalized organic dyes by the inverse-electron-demand Diels-Alder cycloaddition (SPIEDAC). Furthermore, we fine-tuned the SPIEDAC click reaction to obtain an orthogonal variant for rapid protein labeling which we termed selectivity enhanced (se) SPIEDAC. seSPIEDAC and SPIEDAC were combined for the rapid labeling of live mammalian cells with two different fluorescent probes. We demonstrate the strength of our method by visualizing insulin receptors (IRs) and virus-like particles (VLPs) with dual-color super-resolution microscopy. Copyright