- Laboratory scale preparation of 4,4,5,5,5-pentafluoropentan-1-thiol: An important chain of antibreast cancer agents
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Quantitative free radical addition of perfluoroethyl iodide to propargyl alcohol in the presence of sodium hydrosulfite gave E/Z-2-iodo-4,4,5,5,5-pentafluoro-2-penten-1-ols, which were converted to 4,4,5,5,5-pentafluoropentan-1-ol in one step in excellent yield by catalytic hydrogenation over platinum oxide in the presence of triethylamine. 4,4,5,5,5-Pentafluoropentan-1-thiol was obtained in good yield via modified Mitsunobu reaction of the alcohol.
- Li, Xun,Provencher, Louis,Singh, Shankar M.
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Read Online
- Method for preparing 4, 4, 5, 5, 5-pentafluoropentanol
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The invention discloses a method for preparing 4, 4, 5, 5, 5-pentafluoropentanol. The 4, 4, 5, 5, 5-pentafluoropentanol is obtained by one-step method for catalytic oxidation of 1, 1, 1, 2, 2-pentafluoropropane in the presence of a supported noble metal composite catalyst, a solvent and an oxidizing agent, wherein the solvent is water, acetonitrile, isopropanol, dimethylformamide and N-methyl pyrrolidone, the oxidizing agent is an organic peroxide and comprises cumene hydroperoxide, tert-butyl hydroperoxide, acetyl peroxide, benzoyl peroxide, dibenzoyl peroxide, cyclohexanone peroxide, iodosobenzene (PhIO) and m-chloroperbenzoic acid, the mass ratio of the 1, 1, 1, 2, 2- perfluoropropane to the catalyst to the solvent to the oxidizing agent is 1: (0.01-0.1): (0.5-2): (0.05-0.5). The methodfor preparing the 4, 4, 5, 5, 5-pentafluoropentanol, disclosed by the invention, has the advantages of simple reaction operation, high selectivity and mild reaction conditions.
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Paragraph 0011-0033
(2020/04/22)
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- Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate
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Two efficient continuous flow iodoperfluoroalkylation methods are described: using 0.05 mol % perylene diimide (PDI) photocatalyst under 450 nm irradiation or substoichiometric triethylamine under 405 nm irradiation. These methods enable dramatically elevated productivity versus batch processes. The triethylamine-mediated method is explored mechanistically and in substrate scope. The gram-scale synthesis of an active pharmaceutical ingredient side chain is also reported in flow, via a photochemical iodoperfluoroalkylation followed by hydrogenolysis.
- Rosso, Cristian,Williams, Jason D.,Filippini, Giacomo,Prato, Maurizio,Kappe, C. Oliver
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supporting information
p. 5341 - 5345
(2019/07/03)
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- Preparation method of pentafluoropentanol
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The invention discloses a preparation method of pentafluoropentanol. The preparation method comprises the following steps: firstly, synthetic reaction: carrying out a reaction between propenol and pentafluoroethyliodide under the action of a free radical initiator to generate 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol; secondly, hydrogenated dehalogenation reaction: carrying out the hydrogenated dehalogenation reaction under the action of the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol to generate a pentafluoropentanol product. The invention provides the preparation method of the pentafluoropentanol. The pentafluoroethyliodide and the propenol serving the raw material undergo free radical reaction to generate the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol, and the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol undergoes dehalogenation reaction under the action of a reducing agent to generate the pentafluoropentanol. The method is high in reaction yield and easy for industrial production; in addition, the purity of the product is higher than 99 percent.
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Paragraph 0029; 0031; 0033
(2018/01/12)
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- Process for preparing pentafluoropentanol
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4,4,5,5,5-Pentafluoro-1-pentanol is prepared in a particularly advantageous manner from perfluoroethyl iodide by initially adding perfluoroethyl iodide in the presence of a radical initiator which does not carry any acyl groups to allyl alcohol and then hydrogenolytically dehalogenating the resulting 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol in the presence of a catalyst, an acid binder and a diluent.
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- 11β-substituted 14,17-ethanoestratrienes, process for their production and their use as pharmaceutical agents
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The invention relates to 11 β-substituted 14,17-ethanoestratrienes of the general formula 1 STR1 where R 1, R 2 and R 3 are defined in the specification. The compound have antiestrogenic activity and are, therefore, useful for the treatment of estrogen dependent disorders.
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- Synthesis of Amino Acids with Modified Principal Properties 1. Amino Acids with Fluorinated Side Chains
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The synthesis and characterization of chiral fluorinated analogues of norvaline and norleucine from commercially available starting materials are presented.Full experimental details for the synthesis of the following amino acids are given: (S)-4,4-difluoronorvaline, (S)-4,4,5,5,5-pentafluoronorvaline, (S)-5,5-difluoronorleucine, (S)-5,5,6,6,6-pentafluoronorleucine, and (S)-4,4,5,5,6,6,6-heptafluoronorleucine.These compounds were prepared with a view to obtaining new amino acids which possess physical and chemical properties so that their principal properties would be outside the range of variation of hitherto known amino acids.The principal properties are determined as latent variables in principal component analysis of molecular property descriptors.Two of the fluorinated amino acids, (S)-5,5,6,6,6-pentafluoronorleucine and (S)-4,4,5,5,6,6,6-heptafluoronorleucine were found to have principal properties outside the variation of previously characterized natural and synthetic amino acids.The principal properties, z parameters, for the five new fluorinated amino acids are given.
- Larsson, Ulf,Carlson, Rolf,Leroy, Jacques
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p. 380 - 390
(2007/10/02)
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