3023-49-2

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-1-(9-FLUORENYL)ETHANOL is used as a reagent for the preparation of fluorenylethanol via enzymic kinetic resolution by transesterification using lipase. This process allows for the selective production of one enantiomer over the other, which is crucial in the development of chiral drugs. Chiral drugs often exhibit different pharmacological activities and potencies, with one enantiomer being the desired active ingredient while the other may be inactive or even harmful.
In the pharmaceutical industry, the ability to produce a single enantiomer of a chiral drug is essential for ensuring the safety, efficacy, and quality of the final product. Enzymatic kinetic resolution is a green and sustainable method for achieving this goal, as it utilizes enzymes to catalyze the reaction, reducing the need for harsh chemicals and conditions.
Furthermore, (+/-)-1-(9-FLUORENYL)ETHANOL can be used as a building block or intermediate in the synthesis of various pharmaceutical compounds, including those with potential therapeutic applications. Its unique structure and reactivity make it a valuable component in the development of new drugs and drug candidates.

InChI:InChI=1/C15H14O/c1-10(16)15-13-8-4-2-6-11(13)12-7-3-5-9-14(12)15/h2-10,15-16H,1H3

Upstream product

• 2294-82-8 9-ethylfluorene 
• 3300-10-5 9-acetylfluorene 
• 91805-36-6 fluoren-9-ylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 86-73-7 9H-fluorene 
• 136175-23-0 2-benzyl-2-tert-butyl-1-(4-p-tolylsulfonyl)aziridine 
• 63839-88-3 1-(9H-fluoren-9-yl)ethyl acetate 
• 124-41-4 sodium methylate 
• 881-04-9 9H-fluoren-9-yllithium 
• 64-17-5 ethanol 
• 832-80-4 9-diazofluorenone 
• 56954-85-9 9-(1-chloroethyl)fluorene 
• 75-05-8 acetonitrile 
• 56954-84-8 9-(1-bromoethyl)fluorene 

Downstream Products

• 883-20-5 9-methylphenanthrene 
• 7151-64-6 9-ethylidenefluorene 
• 1459213-50-3 (1R)-(+)-1-(9H-fluoren-9-yl)ethyl acetate 
• 107474-78-2 (S)-1-(9H-fluoren-9-yl)ethan-1-ol 
• 107474-78-2 (R)-1-(9H-fluoren-9-yl)ethan-1-ol 
• 170810-97-6 9-<1-<(4'-methylbenzyl)sulfonyl>ethyl>fluorene 

Relevant academic research and scientific papers

First chemoenzymatic synthesis of (R)- and (S)-1-(9H-fluoren-9-yl)ethanol

A simple chemoenzymatic synthesis of 1-(9H-fluoren-9-yl)ethanol stereoisomers is described. The enantiomers were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of commercially available lipases. High-throughput screening and subsequent exhaustive investigation of the utility of the lipases in a stereoselective process of introducing chirality have been carried out. Lipase A from Candida antarctica as a cross-linked aggregate (CAL-A-CLEA) was the most efficient enzyme for the resolution of the title compound providing (S)-1-(9H-fluoren-9- yl)ethanol and its (R)-acetate in enantiopure form (>99% ee). Under mild reaction conditions, excellent enantioselectivity (E = 407), and good isolated yields of the products were obtained.

Solvent-promoted E2 reaction competing with SN2 reaction and stepwise solvolytic elimination and substitution reactions

Solvolysis of 9-(1-X-ethyl)fluorene (1-X, X = I, Br, Cl, OTs, or OBs) in 25 vol % acetonitrile in water gives the elimination products 9-(1-ethylidene)fluorene (3) and 9-vinylfluorene (2) and the substitution products 9-(1-hydroxyethyl)fluorene (1-OH) and

Laser flash photolysis of 9-diazofluorene in low-temperature glasses

The laser flash photolysis of 9-diazofluorene was investigated in several viscous organic glasses at low temperature. The data indicate that triplet fluorenylidene reacts with "soft warm" glasses by classical H atom abstraction, but the mechanism changes to quantum mechanical tunneling in colder and more rigid matrices.

N-S Cleavage Is Faster Than Homolytic Ring Opening in Single-Electron Transfer to Some N-Sulfonylaziridines. Competition between SN2 and SET

The radical anions of the N-sulfonylaziridines, 1a,b and 3 undergo N-S cleavage in place of homolytic ring opening as is demonstrated by reactions with anthracenide A*-.Nucleophilic ring opening of the sulfonylaziridines 1a,b and 3 by the carbanions AH-, X-, and Fl- of dihydroanthracene, xanthene, and fluorene, respectively, proceeds with the expected regioselectivity and is slow enough to allow some competition by a single-electron transfer (SET) initiated N-S cleavage, which provides the desulfonated aziridines and bixanthenyl X-X or bifluorenyl Fl-Fl, respectively.The SET path is favored by light.The competition is in favor of SET to the exclusion of the nucleophilic opening when trityl anion reacts with 1a.The twice-found byproducts 11 and 12 require the azirine intermediate 15, which is, at least formally, generated by elimination of TsH from 1a in a non-SET reaction.

Separation of Amino Acid Enantiomers and Chiral Amines Using Precolumn Derivatization with (+)-1-(9-Fluorenyl)ethyl Chloroformate and Reversed-Phase Liquid Chromatography

A new chiral reagent (+)-1-(9-fluorenyl)ethyl chloroformate (FLEC) was synthesized for separation of amino acid enentiomers and optically active amines.Highly fluorescent diastereomers of amino acids were obtained without racemization within 4 min at room temperature.The derivatives have favorable chromatographic properties, which is demonstrated by a reversed-phase separation of the D and L form of 17 primary amino acids in a single run.The secondary amino acids were resolved separately at a lower pH and can be determined without interferences from primary amino acids.The stability of the derivatives permitted confirmation studies with gas chromatography-mass spectrometry.

Reinvestigation of the Chemistry of Arylcarbenes in Polycrystalline Alcohols at 77 K. Secondary Photochemistry of Matrix-Isolated Carbenes

Photolysis of diphenyldiazomethane (DPDM) in frozen alcoholic matrices gives ground-state triplet diphenylcarbene (DPC).At 77 K 3DPC reacts primarily with alcohols by OH insertion to give ethers.Photolysis of 3DPC produces an excited carbene 3DPC* which reacts with the matrix by H-atom abstraction to ultimately give alcohol-type products.Secondary photolysis of triplet fluorenylidene at 77 K is not as prevalent as that of 3DPC.

Studies of the Borderline between Concerted and Stepwise Mechanisms of Elimination : E1cB Elimination of Fluoren-9-ylmethyl Carboxylate Esters

Rates of β-elimination of carboxylate leaving groups from fluoren-9-ylmethyl carboxylate esters in methanolic sodium methoxide at 25 deg C are reported.An E1cB mechanism with rate-determining formation of a carbanion intermediate is assigned on the basis of near identity of measured elimination rates and rates of carbanion formation predicted from a Taft correlation, and the similarity with elimination of 1-(1-acetoxy-1-methylethyl)indene for which the mechanism has been established by Ahlberg and Thibblin.Values of ρ=0.42 and βlg=0.27 measured for substituted benzoate leaving groups are a little larger than expected (ca. 0.24 and 0.18, respectively) and the discrepancy is tentatively ascribed to conformational enhancement of remote substituent effects, rather than to a contribution of E2 elimination.The effects of alkyl and aryl substitution α to the leaving group are discussed, especially in relation to the borderline between concerted and stepwise mechanisms.The measurements fail to confirm an earlier inference that the borderline shows a discontinuity in transition-state structure at the point of mechanistic change.