1521-51-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Bromocyclohexene is used as a synthetic intermediate for the production of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine, a compound with potential pharmaceutical applications. Its unique structure allows for the creation of complex molecules that can be used in the development of new drugs.
Used in Chiral Compound Synthesis:
In the field of chiral chemistry, 3-bromocyclohexene is used as a key building block for the synthesis of enantiopure cyclohexitols such as muco-quercitol, D-chiro-inocitol, and allo-inocitol. These cyclohexitols have various applications in the pharmaceutical and chemical industries, including the development of drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
3-Bromocyclohexene's unique chemical properties make it a valuable compound for research purposes. It can be used to study the reactivity of brominated hydrocarbons and their interactions with other molecules, contributing to the advancement of chemical knowledge and the development of new synthetic methods.
Used in Material Science:
The properties of 3-bromocyclohexene can also be exploited in the development of new materials with specific characteristics, such as improved stability or reactivity. Its use in material science can lead to the creation of novel materials with applications in various industries, including electronics, coatings, and adhesives.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3863, 1985 DOI: 10.1016/S0040-4039(00)89271-0

InChI:InChI=1/C6H9Br/c7-6-4-2-1-3-5-6/h2,4,6H,1,3,5H2/t6-/m1/s1

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 110-83-8 cyclohexene 
• 3699-18-1 N-bromoglutarimide 
• 7072-23-3 1,3-dibromo-5,5-dimethyl-hydantoin 
• 2439-85-2 N-bromophthalimide 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 5401-62-7 1,2-dibromocyclohexane 
• 1165952-92-0 cyclohexa-1,4-diene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 426-46-0 pentafluoro-propionic acid bromoamide 
• 79-15-2 N-bromoacetamide 
• 29623-43-6 Bicyclo<3.1.0>hexan-exo-6-amin 

Downstream Products

• 61862-37-1 (2-cyclohexen-1-yl)piperidine 
• 853920-96-4 cyclohex-2-enyl-[2]thienyl-acetonitrile 
• 58008-22-3 2-cyclohex-2-enyl-cyclohexane-1,3-dione 
• 5558-37-2 2-(cyclohex-2-en-1-yl)-2-phenylacetonitrile 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 66950-33-2 N,N-dimethylamino-1-cyclohex-2-ene 
• 115125-55-8 3-(p-tolylthio)cyclohexene 
• 3983-07-1 3-n-butylcyclohexene 
• 855264-82-3 4-cyclohex-2-enyloxy-3,5-diiodo-benzaldehyde 
• 4104-56-7 3-(2-methylpropyl)cyclohexene 
• 111664-12-1 2-(2'-cyclohexenyl)naphthalene 
• 100192-55-0 3-(4-nitrophenoxy)cyclohex-1-ene 
• 14072-87-8 3-(tert-butyl)cyclohexene 
• 3983-08-2 3-isopropylcyclohexene 

Relevant academic research and scientific papers

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades

A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.

N-(4-Methoxyphenyl)-substituted bicyclic isothioureas: effect on morphology of cancer cells

Bicyclic isothioureas of N-(4-methoxyphenyl)-2-aminocycloalkane[d]thiazole type were obtained using intramolecular electrophilic cyclization of N-(cycloalk-2-enyl)-N′-(4-methoxyphenyl)thioureas. Isothiourea fused with sevenmembered ring caused noticeable

A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones

Reported herein is a visible-light-catalyzed photoredox atom-transfer radical cyclization (ATRC) halo-alkylation of 1,6-dienes with α-halo-ketones as the ATRC reagent. This process exhibits high atom economy, high step economy, and high redox economy, which can directly construct a 4-bromo-3,3-dialkyl-octahydro-indol-2-one core under mild conditions in one pot, and lutidine is found to be the key promoter for this ATRC process.

Silver-promoted cascade radical cyclization of γ,δ-unsaturated oxime esters with P(O)H compounds: synthesis of phosphorylated pyrrolines

A cascade radical cyclization was realized for the first silver-promoted imino-phosphorylation of γ,δ-unsaturated oxime esters, which provided a step-economical and redox-neutral route to access a variety of phosphorylated pyrrolines in good to excellent yields. Moreover, a new bulky trivalent phosphine ligand with a pyrroline motif was obtained through a deoxidation process.

Synthesis of pentacyclic compounds via intramolecular [3 + 2] photocycloaddition of cycloalkene linked naphthalenes

Intramolecular photocycloaddition reactions of cycloalkene linked naphthalenes lead to formation of pentacyclic compounds in a high yielding and stereoselective manner. Intramolecular [2 + 2] cycloadducts are formed initially in photoreactions of cycloalkene linked 1-cyanonaphthalenes. The initially formed intramolecular [2 + 2] cycloadducts absorb light at wavelengths used to promote the photochemical reactions and, as a result, they undergo efficient photocycloreversion to regenerate the starting substrates. In a less efficient competing process, the cycloalkene linked 1-cyanonaphthalenes react to form [3 + 2] intramolecular photoadducts, which do not absorb incident light under the conditions used. Consequently, these photoadducts become the major products in these processes. The relative configuration of the major diastereomers of the pentacyclic products formed from photoreactions of cyclopentene linked naphthalenes (cis-cis) differ from those (cis-trans) arising from the cyclooctene linked substrates. The results of theoretical calculations, which show that steric factors govern the preferred facial mode of intramolecular addition, are in good agreement with the stereochemical course of these photoreactions.

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

Preparation of polycyclic compounds by intramolecular photospirocyclization and photocycloaddition reactions of 4-alkenyl-1-cyanonaphthalene derivatives

Photoreactions of 4-pentenyl-1-cyanonaphthalenes yield spirocyclic products along with [4?+?2] cycloadducts. Photoreactions of 5-phenyl derivatives produce a product having tricyclo[6.3.0.01,4]undecadiene skeleton. Formation of angular triquinanes takes place in photoreactions of cycloalkene-linked cyanonaphthalenes. The observation demonstrates that π–π arene ring interactions, steric hindrance, and suitable locations of reaction sites in syn and anti singlet exciplexes govern the modes followed in intramolecular photoreactions of 4-alkenyl-1-cyanonaphthalenes.

Trihaloisocyanuric Acid/Triphenylphosphine: An Efficient System for Regioselective Conversion of Epoxides into Vicinal Halohydrins and Vicinal Dihalides under Mild Conditions

A new synthetic method has been developed for the regioselective conversion of epoxides to vicinal chloro-/bromohydrins and vicinal dihalides by reaction with the system trihaloisocyanuric acid/tri?phenylphosphine in acetonitrile under mild and neutral conditions. The reactions proceed smoothly in high yield at room temperature and at reflux, respectively, over a short time.

Hydroxylation versus Halogenation of Aliphatic C?H Bonds by a Dioxygen-Derived Iron–Oxygen Oxidant: Functional Mimicking of Iron Halogenases

An iron–oxygen intermediate species generated in situ in the reductive activation of dioxygen by an iron(II)–benzilate complex of a monoanionic facial N3ligand, promoted the halogenation of aliphatic C?H bonds in the presence of a protic acid and a halide anion. An electrophilic iron(IV)–oxo oxidant with a coordinated halide is proposed as the active oxidant. The halogenation reaction with dioxygen and the iron complex mimics the activity of non-heme iron halogenases.

The radical reaction from a fluorine-containing compound

PROBLEM TO BE SOLVED: To provide a radical reaction substitute solvent for carbon tetrachloride which has been used heretofore as a radical reaction solvent. SOLUTION: A chain fluorine-containing hydrocarbon represented by formula (1): CmH2m+2-nFn(wherein m is an integer of 3-10 and n is an integer of 1 to 2m+1) or a cyclic fluorine-containing hydrocarbon represented by formula (2): CpH2p-qFq(wherein p is an integer of 3-10 and q is an integer of 1 to 2p-1) is used as a solvent for various radical reactions. COPYRIGHT: (C)2011,JPO&INPIT