147991-84-2

Usage

Uses

Used in Scientific Research:
(S)-(-)-1,1,1-TRIFLUORONONAN-2-OL is used as a chemical building block for the synthesis of more complex molecules in the field of organic chemistry. Its unique structure and functional groups make it a valuable component in the development of new compounds with potential applications in various industries.
Used in Chemical Studies:
(S)-(-)-1,1,1-TRIFLUORONONAN-2-OL is used as a research compound in the study of chemical reactions and mechanisms. Its chiral configuration and trifluoro component provide insights into the behavior of molecules with similar structures, contributing to the understanding of chemical processes and the design of new chemical entities.
Used in Pharmaceutical Development:
(S)-(-)-1,1,1-TRIFLUORONONAN-2-OL is used as a potential precursor in the synthesis of pharmaceutical compounds. Its unique properties may contribute to the development of new drugs with improved efficacy and reduced side effects, making it a valuable asset in the field of medicinal chemistry.
Used in Material Science:
(S)-(-)-1,1,1-TRIFLUORONONAN-2-OL is used as a component in the development of new materials with specific properties, such as improved thermal stability, chemical resistance, or enhanced reactivity. Its incorporation into material formulations can lead to the creation of innovative products with applications in various industries, including electronics, automotive, and aerospace.

InChI:InChI=1/C9H17F3O/c1-2-3-4-5-6-7-8(13)9(10,11)12/h8,13H,2-7H2,1H3/t8-/m0/s1

Upstream product

• 26902-66-9 1,1,1-trifluorononan-2-one 
• 106-32-1 octanoic acid ethyl ester 

Downstream Products

• 128054-80-8 (S)-(-)-1-(trifluoromethyl)octyl p-hydroxybenzoate 

Relevant academic research and scientific papers

Two Classes of Enzymes of Opposite Stereochemistry in an Organism: One for Fluorinated and Another for Nonfluorinated Substrates

Reduction of methyl ketones by dried cells of Geotrichum candidum (APG4) afforded (S)-alcohols in excellent enantiomeric excess (ee), whereas the reduction of trifluoromethyl ketones gave the corresponding alcohols of the opposite configuration also in excellent ee. The replacement of the methyl moiety with a trifluoromethyl group alters both the bulkiness and the electronic properties, the effect of which on the stereoselectivity was examined. No inversion in stereochemistry was observed in the reduction of hindered ketones such as isopropyl ketone, while the stereoselectivity was inverted in the reduction of ketones with electron-withdrawing atoms such as chlorine. The mechanism for the inversion in stereochemistry was investigated by enzymatic studies. Several enzymes with different stereoselectivities were isolated; one of them catalyzed the reduction of methyl ketones, and another with the opposite stereoselectivity catalyzed the reduction of trifluoromethyl ketones. Furthermore, both APG4 and the isolated enzyme were applied to the reduction of fluorinated ketones on a preparative scale, which resulted in the synthesis of chiral fluorinated alcohols with excellent ee.

Different stereochemistry for the reduction of trifluoromethyl ketones and methyl ketones catalyzed by alcohol dehydrogenase from Geotrichum

Reduction of trifluoromethyl ketones by a crude alcohol dehydrogenase from Geotrichum affords (S)-trifluoromethyl carbinols in excellent ee, whereas the reduction of methyl ketones gives the corresponding alcohols of the opposite configuration in excellent ee.

Chiral Synthesis Via Organoboranes. 38 Selective Reductions. 48. Asymmetric Reduction of Trifluoromethyl Ketones by B-Chlorodiisopinocampheylborane in High Enantiomeric Purity

(-)-B-Chlorodiisopinocampheylborane TM,1>, introduced by us several years ago, has been shown to reduce prochiral aryl and alkyl perfluorinated ketones to the corresponding optically active alcohols in very high ee.For example, 2,2,2-trifluoroacetophenone, trifluoroacetyl-1-naphthalene, and trifluoroacetyl-2-naphthalene are all reduced with 1 within 1-3 d at rt in 90percent ee, 78percent ee and 91percent ee, respectively.The optical purity of 1-phenyl-2,2,2-trifluoroethanol is upgraded to = 99percent ee by crystallizing the initially formed products from pentane. 1,1,2,2,2- pentafluoropropiophenone and 1,1,2,2,3,3,3-heptafluorobutyrophenone are reduced in 3 d with 1 to the corresponding alcohols in 92percent ee and 87 percent ee, respectively.The reagent reduces alkyl trifluoromethyl ketones at a rate faster than that of the aryl derivatives, while still providing the product alcohols in very high ee.Thus, 1,1,1-trifluoroacetone, 1,1,1-trifluorononan-2-one, and 1,1,1-trifluorodecan-2-one are all reduced within 4 - 8 h in 89percent ee, 92percent ee, and 91percent ee, respectively.Even α-sec-alkyl trifluoromethyl ketones are handled by 1 very efficiently.Thus cyclohexyl trifluoromethyl ketone is reduced by 1 at rt in 12 h to the product alcohol in 87percent ee.In all of these cases the trifluoromethyl group acts as the enantiocontrolling larger group as compared to the aryl or alkyl group.This produces alcohol products with stereochemistry opposite to those obtained for the corresponding hydrogen analogs.The steric and electronic influence of the trifluoromethyl group in achieving enantiocontrol in assymmetric reductions is discussed.Keywords: asymmetric reduction; trifluoromethyl ketones; DIP-Chloride; high enantiomeric purity