5181-75-9

Usage

Uses

Used in Chemical Synthesis:
(1 1'-BICYCLOPENTYL)-1 1'-DIOL 97 is used as a key intermediate in the synthesis of various organic compounds, including (BptdH-2)SeO, a cyclic selenite. This application takes advantage of its unique structure and reactivity, allowing for the creation of new molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1 1'-BICYCLOPENTYL)-1 1'-DIOL 97 may be utilized as a building block for the development of new drugs or drug candidates. Its symmetrical structure and functional groups can be exploited to design molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
(1 1'-BICYCLOPENTYL)-1 1'-DIOL 97 can be employed in the development of new materials, such as polymers or coatings, due to its unique chemical structure. Its hydroxyl groups can participate in various chemical reactions, enabling the creation of materials with specific properties, such as improved strength, durability, or chemical resistance.
Used in Research and Development:
As a symmetrical 1,2-diol, (1 1'-BICYCLOPENTYL)-1 1'-DIOL 97 can be a valuable compound for research and development purposes. It can be used as a model compound to study the effects of bicyclic structures on chemical reactivity, or as a starting material for the synthesis of more complex molecules with potential applications in various fields.

Upstream product

• 108-94-1 cyclohexanone 
• 120-92-3 cyclopentanone 
• 556-56-9 allyl iodid 
• 75-09-2 dichloromethane 
• 74-88-4 methyl iodide 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 7440-45-1 cerium 
• 763-51-9 diethyl 2-bromosuccinate 
• 106-95-6 allyl bromide 

Downstream Products

• 13388-94-8 spiro[4.5]decan-6-one 
• 934-02-1 bicyclopentyl-1,1'-diene 
• 91328-28-8 1,1'-diacetoxy-1,1'-bicyclopentane 
• 91328-29-9 11,13-Dioxa-dispiro[4.0.4.3]tridecan-12-one 
• 2866-71-9 (1,1'-bicyclopentyl)-2-one 
• 16189-35-8 bicyclopentylidene 
• 91328-40-4 2-acetonyl-2-hydroxy-4,4:5,5-bis(tetramethylene)-1,3-dioxolane 
• 67-64-1 acetone 
• 1636-39-1 bicyclopentyl 
• 1076-17-1 hexahydroindacene 
• 120-92-3 cyclopentanone 

Relevant academic research and scientific papers

Renewable high-density spiro-fuels from lignocellulose-derived cyclic ketones

Renewable high-density spiro-fuels are synthesized from lignocellulose-derived cyclic ketones for the first time, which show higher density, higher neat heat of combustion and lower freezing point compared with other biofuels synthesized from the same feedstock, and thus represent a new type of renewable high-density fuel attractive for practical applications.

MeOH or H2O as efficient additive to switch the reactivity of allylSmBr towards carbonyl compounds

A variety of carbonyl compounds were treated by allylSmBr (allylSmBr) with MeOH as the cosolvent to have further insights on the previously reported reductive coupling of aryl ketones mediated by Sm/alkyl halide/MeOH. The results demonstrate that the real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr, and MeOH has elegantly switched the reactivity of allylSmBr from being nucleophilic to being good reductive coupling reagent. Besides, H2O was also found to be a useful additive to realize the pinacol coupling of aliphatic aldehydes and ketones promoted by allylSmBr.

Cerium metal-mediated Reformatsky-type reaction with ethyl bromosuccinate for the synthesis of novel paraconic acid analogs

The treatment of cerium metal with ethyl bromosuccinate (1) forms the stabilized organolanthanoid intermediate (2), which reacts with carbonyl compounds in a Reformatsky-type reaction, under mild conditions, to produce functionalized γ-substituted paraconic acids (4) in good yields.

Exploring SmBr2-, SmI2-, and YbI2-mediated reactions assisted by microwave irradiation

The use of microwave heating in lanthanide(II) halide (LnX2 = SmBr2, SmI2, and YbI2) mediated reduction and coupling reactions has been investigated for a variety of functional groups including α,β-unsaturated esters, aldehydes, ketones, imines, and alkyl halides. Good to quantitative transformations were obtained within a few minutes without the addition of any co-solvents, such as hexamethyl phosphoramide (HMPA). The redox potential of YbI2 in tetrahydrofuran (THF) has been determined as -1.02± 0.05 V (versus Ag/AgNO3) by cyclic voltammetry. A large selectivity difference in various reactions was observed depending on the redox potential of the LnX2 reagent. The more powerful reductant, SmBr2, afforded mainly pinacol-coupling products of ketones whereas the weaker reductant YbI2 afforded mainly reduction products. The results indicate that the reducing power of LnX 2 has a large impact on not only the pinacol coupling/reduction product ratio of ketones but also on other substrates in which there are competing coupling and reduction reactions. The use of in situ generated LnX2 has also been explored and proven useful in many of these reactions.

Alkylative Reduction of Titanium(IV) Isopropoxide with EtMgBr: Convenient Method for the Generation of Subvalent Titanium Alkoxide Reagents and their Reactivity in Pinacol Coupling Reactions

The composition of the gaseous products from the reaction of Ti(IV) isopropoxide with ethylmagnesium bromide in diethyl ether evidences the formation of subvalent titanium isopropoxide species in various oxidation states depending on relative amounts of the reactants. Reaction of titanium(IV) isopropoxide with one equivalent of the Grignard reagent gives presumably titanium(III) isopropoxide. The latter is generated as a result of disproportionation of starting Ti(IV) species and titanium(II) isopropoxide-ethene complex which is formed as a result of ethane extrusion from diethyltitanium(IV) isopropoxide. Titanium(III) isopropoxide prepared by this way transforms the aldehydes and the aromatic ketones into the corresponding pinacols in good yields.

Dichloromethane as a source of the CH22-synthon: A combination of an arene-catalysed lithiation and a barbier-type reaction

The reaction of dichloromethane 1 with an excess of lithium powder (1:7 molar ratio) and catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of a carbonyl compound 2 (1:2 molar ratio) in tetrahydrofuran at -40°C yields, after hydrolysis, the corresponding 1,3-diols 3 in moderate yields. The process can be also applied to more complicated gem-dichloro derivatives such as 7,7-dichlorobicyclo[4.1.0]heptane 6 or methyl dichloromethyl ether 9.

Study of I-strain relief in the intermediate when forming spiro ketones from unsymmetrical cycloalkylidenecycloalkanes, their dibromides, and their pinacols

Three unsymmetrical intercyclic olefins, their dibromides, and their pinacols were prepared, each so the two carbons involved at the functional group were part of a different sized ring. The pinacols were reacted with 25% sulfuric acid and with boron trif

Magnesium- and Titanium-induced Reductive Coupling of Carbonyl Compounds: Efficient Syntheses of Pinacols and Alkenes

Finely dispersed magnesium on graphite was found to be a totally selective single-electron transfer reagent of general utility for the reduction of various kinds of carbonyl and dicarbonyl compounds to pinacols, a reaction quite compatible with a number of functional groups.Similarly, titanium on graphite proved to be a universally applicable reducing agent for the efficient conversion of pinacols, carbonyl and dicarbonyl compounds into alkenes and cycloalkenes respectively and for the cyclization of oxo alkanoates to enol ethers, facilitating and unifying the highly useful McMurry reaction.The practicability of the presently known carbonyl coupling methods is discussed in the light of these results.