4103-10-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 5129, 1956 DOI: 10.1021/ja01600a088

InChI:InChI=1/C9H14O2/c10-9(11)8-6-4-2-1-3-5-7-8/h1-2,8H,3-7H2,(H,10,11)/b2-1-

Upstream product

• 6335-43-9 2-(Pyrrolidin-1-yl)bicyclo[3.3.1]nonan-9-on 
• 74-88-4 methyl iodide 
• 19835-69-9 cyclooct-4-enecarboxaldehyde 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 124-38-9 carbon dioxide 
• 1131-74-4 ethyl (Z)-cyclooct-4-ene-1-carboxylate 
• 5259-72-3 cyclo-octa-1,5-diene 
• 4103-12-2 5-bromocyclooct-1-ene 
• 62672-96-2 N-(1-cyclohexen-1-yl)-1H-pyrrole 
• 107-02-8 acrolein 
• 17223-82-4 (Z)-5-bromocyclooct-1-ene 
• 112654-91-8 (Z)-cyclooct-4-ene-1-carbonitrile 

Downstream Products

• 50653-82-2 cyclooct-4-ene-1-carbonyl chloride 
• 3637-63-6 cyclooctylmethanol 
• 3724-54-7 methyl cyclooctanecarboxylate 
• 280-65-9 bicyclo[3.3.1]nonane 
• 4744-89-2 4-Hydroxy-cyclooctancarbonsaeurelacton 
• 15973-61-2 5-cyclooctenecarbonyl chloride 
• 71404-71-2 (1α,5β,6α)-5-(phenylseleno)-7-oxabicyclo<4.2.2>decan-8-one 
• 75826-37-8 (1α,4β,5α)-4-(phenylseleno)-6-oxabicyclo<3.3.2>decan-7-one 

Relevant academic research and scientific papers

Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics

The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans-cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO-linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.

COMPOUNDS FOR FAST AND EFFICIENT CLICK RELEASE

The invention disclosed herein relates to compounds, combinations, kits, and methods using same, for use in bioorthogonal release reactions. In particular, the compounds, combinations and kits of the invention can be used to achieve fast and efficient click release. Applications of the compounds, combinations, and kits of the invention include both in vitro and in vivo applications.

Targeted and modular architectural polymers employing bioorthogonal chemistry for quantitative therapeutic delivery

There remain several key challenges to existing therapeutic systems for cancer therapy, such as quantitatively determining the true, tissue-specific drug release profile in vivo, as well as reducing side-effects for an increased standard of care. Hence, it is crucial to engineer new materials that allow for a better understanding of the in vivo pharmacokinetic/pharmacodynamic behaviours of therapeutics. We have expanded on recent "click-to-release" bioorthogonal pro-drug activation of antibody-drug conjugates (ADCs) to develop a modular and controlled theranostic system for quantitatively assessing site-specific drug activation and deposition from a nanocarrier molecule, by employing defined chemistries. The exploitation of quantitative imaging using positron emission tomography (PET) together with pre-targeted bioorthogonal chemistries in our system provided an effective means to assess in real-time the exact amount of active drug administered at precise sites in the animal; our methodology introduces flexibility in both the targeting and therapeutic components that is specific to nanomedicines and offers unique advantages over other technologies. In this approach, the in vivo click reaction facilitates pro-drug activation as well as provides a quantitative means to investigate the dynamic behaviour of the therapeutic agent.

CHANNEL PROTEIN ACTIVATABLE LIPOSOMES

Disclosed is a liposome, comprising a lipid bilayer enclosing a cavity, wherein the bilayer comprises a channel protein releasably linked to an eight-membered non-aromatic cyclic alkenylene group, preferably a cyclooctene group, and more preferably a trans-cyclooctene group. The liposomes are used in a kit comprising the liposome, the liposomal membrane of which comprises a channel protein linked to a Trigger, and an Activator for the Trigger, wherein the Trigger comprises the eight- membered non-aromatic cyclic alkenylene group, and the Activator comprises a diene.

ACTIVATABLE LIPOSOMES

Disclosed are reactive liposome, comprising a lipid bilayer enclosing a cavity, wherein the bilayer comprises a linkage to an eight-membered non-aromatic cyclic alkenylene group, preferably a cyclooctene group, and more preferably a trans-cyclooctene group. The liposomes are use in a kit comprising the liposome linked, directly or indirectly, to a Trigger, and an Activator for the Trigger, wherein the Trigger comprises an eight-membered non-aromatic cyclic alkenylene group, and the Activator comprises a diene.

CHEMICALLY CLEAVABLE GROUP

Disclosed is the use of the reactive components of the inverse electron-demand Diels Alder reaction for chemical masking and unmasking in vitro. This can be applied in complex chemical reactions and, particularly in the synthesis of biomolecules, e.g. on solid supports. The reactice components are a dienophile, particularly a trans-cyclooctene, and a diene, particularly a tetrazine.

BIO-ORTHOGONAL DRUG ACTIVATION

Disclosed is a kit for the administration and activation of a Prodrug. The kit comprises a Masking Moiety linked, directly or indirectly, to a Trigger moiety, which in turn is linked to a Drug, and an Activator for the Trigger moiety. The Trigger moiety comprises a dienophile and the Activator comprises a diene, whereby the dienophile is an eight-membered non- aromatic cyclic alkenylene group, preferably a cyclooctene group, and more preferably a trans-cyclooctene group. The Trigger and the Activator undergo a fast, bio-orthogonal reaction resulting in the release of the Masking Moiety, and activation of the drug.

POLYMERIC SALEN COMPOUNDS AND METHODS THEREOF

The present disclosure provides a polymerizable compound of the formula (I) where the R1, R2, R’1, R’2, X1 to X8, Y1, Y2, M and L have any of values as defined in the

Ni0-induzierte Herstellung cyclischer C8-Carbonsaeuren aus Cyclooctenen und Kohlendioxid

Cyclooctene and 1,5-cyclooctadiene are shown to be ideal substrates for coupling reactions with CO2 on (Lig)Nickel(0)-systems.By variation of the ligands and addition of promotors, it is possible by successive application of carbon dioxide, carbon monoxid

Mechanistic Aspects of Oxygen Transfer by gem-Dialkylperoxonium Ions

Monocyclic gem-dialkylperoxonium ion 2 has been generated from the reaction of 1-bromo-4-hydroperoxy-4-methylpentane (1) with silver tetrafluoroborate or trifluoroacetate, and related bicyclic ion 4 has been formed from the reaction of 5-hydroxyperoxycyclooctene (3) with N-bromosuccinimide.These species have been shown to oxidize efficiently both dialkyl sulfoxides and methyl phenyl sulfide.Reaction with thianthrene 5-oxide afforded XNu values of 0.10 for 2 and 0.72 for 4, while competition reactions with (p-XC6H4)2SO (X=Me, H, F, and Cl) yielded Hammett ρ values (versus ?) of -0.83+/-0.11 and -1.77+/-0.58.These results indicate that gem-dialkylperoxonium ion salts,R2O+-OH,X-, are electrophilic oxygen transfer reagents, tunable to some extent by choice of R1, R2, and X, but provide no evidence of deprotonation to the corresponding dioxygen ylide under the conditions studied.