72345-23-4

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-(+)-Pentanediol is used as an optically active reagent for the preparation of NIP-101, a potent calcium antagonist. (2S,4S)-(+)-PENTANEDIOL plays a crucial role in the development of medications that help regulate calcium levels in the body, which can be beneficial for treating conditions such as hypertension and certain heart disorders.
Used in Chemical Synthesis:
(2S,4S)-(+)-Pentanediol, due to its unique stereochemistry and functional groups, can be employed as a building block in the synthesis of various chiral compounds. These compounds find applications in the production of pharmaceuticals, agrochemicals, and other specialty chemicals that require specific stereochemistry for their biological activity.
Used in Research and Development:
The optical activity of (2S,4S)-(+)-Pentanediol makes it an essential tool in research and development for studying the effects of stereochemistry on the properties and reactivity of molecules. It can be used to investigate the mechanisms of various chemical reactions and to develop new methods for the synthesis of enantiomerically pure compounds.

InChI:InChI=1/C5H12O2/c1-2-3-4-5(6)7/h5-7H,2-4H2,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 107-89-1 acetaldol 
• 4161-60-8 4-hydroxypentan-2-one 
• 123-54-6 acetylacetone 
• 17615-19-9 3,4-pentadien-2-ol 
• 63315-69-5 (-)-(4R)-4-hydroxypentan-2-one 
• 22520-29-2 syn-3,4-epoxy-2-pentanol 
• 56-81-5 glycerol 
• 7570-05-0 trans-4,6-dimethyl-2-oxo-1,3-dioxane 
• 150616-71-0 C₂₇H₄₆N₂O₆ 
• 1825-14-5 DL-pentan-2,4-diol 
• 17227-17-7 2,2,4,6-tetramethyl-[1,3]dioxane 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 

Downstream Products

• 94309-72-5 2,4-bis-phenylcarbamoyloxy-pentane 
• 42075-32-1 (2R,4R)-pentanediol 
• 4161-60-8 4-hydroxypentan-2-one 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 123-54-6 acetylacetone 
• 19398-53-9 2,4-dibromopentane 
• 62118-71-2 (4RS,6SR)-2-phenyl-2,4,6-trimethyl-1,3-dioxane 
• 1825-14-5 DL-pentan-2,4-diol 
• 170806-28-7 4-hydroxypentan-2-yl 4-toluenesulfonate 
• 695816-49-0 [2-((4S,6S)-dimethyl-[1,3]dioxan-2-yl)phenyl]phosphane 
• 695816-48-9 [2-((4S,6S)-dimethyl-[1,3]dioxan-2-yl)phenyl]phosphonic acid diethyl ester 
• 24347-99-7 syn-pentane-2,4-diyl bis(4-methylbenzenesulfonate) 
• 5954-76-7 threo-(2S,4R)-pentanedithiol 

Relevant academic research and scientific papers

Isolation of Racemic 2,4-Pentanediol and 2,5-Hexanediol from Commercial Mixtures of Racemic and Meso Isomers by way of Cyclic Sulfites

Enantiomerically pure diols with C2 symmetry such as 2,3-butanediol, 1, 2,4-pentanediol, 2, and 2,5-hexanediol, 3, are useful chiral auxiliaries, but they are expensive because chemists lack good synthetic routes that eliminate both the meso isomer and one enantiomer.Enzymic resolutions efficiently separate the enantiomer, but do not remove the meso isomer.To simplify enzymic resolutions of 2 and 3, we developed simple methods to isolate the racemic isomer from commercial mixtures of racemic and meso isomers 1 or 2, the meso isomer selectivity reacted with SOCl2 to give a cyclic sulfite that was removed by column chromatography to leave (+/-)-2, 92percent de, 1.4 g, 55percent yield.For 3, both meso and racemic isomers reacted with SOCl2 to give cyclic sulfites, but the sulfite derived from the meso isomer rearranged to trans-2,5-dimethyltetrahydrofuran under acidic conditions.Hydrolysis of the remaining sulfite gave (+/-)-3, 84percent de, 1.1 g, 37percent yield.Resolution of (+/-)-2 and (+/-)-3 using lipase from Pseudomonas cepacia yielded (2R,4R)-2-diacetate, 78 percent ee, >97percent de, 40percent of theory and (2R,5R)-3-diacetate, 94percent ee, >97percent de, 47percent of theory.Previously reported acetylations of 2 and 3 by lipase from Candida antarctica (CAL) or by lipase from Pseudomonas sp. (Amonolipase AK) are more enantioselective and thus, the best route to enantiomerically and diastereomerically pure 2 and 3 is removal of the meso isomer by way of cyclic sulfites followed by resolution with CAL or Amano lipase AK.

Synthesis and Applications of (Pyridyl)imine Fe(II) Complexes as Catalysts in Transfer Hydrogenation of Ketones

Abstract: Chiral (pyridyl)imine Fe(II) complexes, [Fe(L1)3]2+[PF6?]2, (Fe1), [Fe(L2)3]2+[PF6?]2, (Fe2), [Fe(L3)3]2+[PF6?]2 (Fe3), and [Fe(L4)3]2+[PF6?]2 (Fe4) were synthesised by reactions of synthons (S-)-1-phenyl-N-(pyridine-2-yl) ethylidine)ethanamine (L1), (R-)-1-phenyl-N-(pyridine-2-yl) ethylidine) ethanamine (L2), (S)-1-phenyl-N-(pyridine-2-yl methylene) ethanamine (L3) and (S)-1-phenyl-N-(pyridine-2-yl methylene)ethanamine (L4) with the FeCl2 salt. The solid-state structure of complex Fe4 showed that the?Fe atom contains three units of bidentate bound ligand L4 to form a six-coordinate cationic compound. The Fe(II) complexes were evaluated as catalysts in asymmetric transfer hydrogenation of ketones reactions and showed moderate catalytic activities with low enantioselectivity. Catalytic activities of the respective complexes were regulated by the nature of the metal complexes, ketone substrate and reaction conditions. Mercury and sub-stoichiometric poisoning experiments implicate possible formation of both active Fe(0) nanoparticles and Fe(II) homogeneous intermediates. Graphic Abstract: [Figure not available: see fulltext.]

Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.

Total Synthesis of (?)-Histrionicotoxin through a Stereoselective Radical Translocation–Cyclization Reaction

Stereoselective total syntheses of (?)-histrionicotoxin and (?)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation–cyclization reaction involving a chiral cyclic acetal; the use of tris(trimethylsilyl)silane was crucial for the high diastereoselectivity. The cyclization product was converted into (?)-histrionicotoxin 235A through a one-pot partial-reduction–allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (?)-histrionicotoxin.

WATER-INSOLUBLE RUTHENIUM CATALYST COMPOSITION FOR USE IN AQUEOUS HYDROGENATION REACTIONS

The invention relates to a method for converting a precatalyst complex to an active catalyst complex, wherein the precatalyst complex and the active catalyst complex comprise a ruthenium atom and an optically active ligand that is insoluble in water, and the active catalyst complex furthermore comprises a monohydride and a water molecule. The method comprises the steps of providing water as an activation solvent system with a pH value equal or below 2, and solving said precatalyst complex, an acid, and hydrogen therein. The invention further relates to a method for manufacturing a catalyst composition, a method for hydrogenating a substrate molecule and a reaction mixture.

Method for preparing beta-diol from beta-diketone

The invention relates to a method for preparing beta-diol from beta-diketone. The method is characterized in that beta-diketone contacts and reacts with hydrogen in the presence of a hydrogenation catalyst under fixed bed reaction conditions, the hydrogenation catalyst comprises an active component copper and a carrier, and the hydrogenation catalyst preferably comprises an assistant component selected from VIIIB and IB group elements, the assistant is preferably selected from one or more of Ni, Co and Ag, and the carrier is SiO2. The method adopting a fixed bed hydrogenation technology and using a copper-containing supported catalyst has the advantages of no pollution to environment, mild operating conditions, and suitableness for continuous production.

Method for preparing beta-diol from beta-diketone by hydrogenation

The invention relates to a method for preparing beta-diol from beta-diketone by hydrogenation. The method comprises the following steps: in the presence of a catalyst and under the fixed-bed hydrotreating reaction condition, enabling beta-diketone to be in contact with hydrogen, so as to obtain beta-diol, wherein the catalyst contains CuO and ZnO, preferably also contains Al2O3, and more preferably also contains alkali metal oxides. According to the method for preparing beta-diol from beta-diketone by hydrogenation, provided by the invention, the technology of continuously producing beta-diol by adopting a fixed bed device is realized, the technology is simple and convenient to operate, the utilization ratio of raw materials and the production efficiency of products are improved, the reaction does not need to be carried out under high pressure, and potential safety hazards are reduced.

A β-diketone fixed bed hydrogenation method for preparing β-diol (by machine translation)

The invention relates to a β-diketone fixed bed hydrogenation method for preparing β-diol, including in the presence of hydrogenation catalyst under conditions and fixed bed reaction of the β-diketone reaction contact with hydrogen gas; the hydrogenation catalyst comprises active component copper and carrier, wherein in order to weight part, the content of copper is 20-35 parts, carrier is in a content of 60-80 parts. Preferably, the hydrogenation catalyst also includes selected from group IB and VIIIB additive component, more preferably the assistant is selected from Ni, Ag Co and in one or several of, the carrier is SiO 2. The method provided by the present invention which adopts a fixed bed hydrogenation process and the use of copper-containing supported catalyst, no pollution to the environment, mild operating conditions, is suitable for continuous production. (by machine translation)

Method for preparation of beta-diol

The present invention relates to a method for preparation of a beta-diol from a beta-diketone by hydrogenation, the method comprises contact reaction of the beta-diketone and hydrogen in the presence of a hydrogenation catalyst and under fixed bed reaction conditions, the hydrogenation catalyst is a non-noble metal catalyst, includes a metal component and a carrier, and can be prepared by a conventional method. The method uses a fixed bed hydrogenation process, and is free of environmental pollution, mild in operating conditions, and suitable for continuous production.

Water-insoluble Ruthenium catalyst composition for use in aqueous hydrogenation reactions

The invention relates to a method for converting a precatalyst complex to an active catalyst complex, wherein the precatalyst complex and the active catalyst complex comprise a ruthenium atom and an optically active ligand that is insoluble in water, and the active catalyst complex furthermore comprises a monohydride and a water molecule. The method comprises the steps of providing water as an activation solvent system with a pH value equal or below 2, and solving said precatalyst complex, an acid, and hydrogen therein. The invention further relates to a method for manufacturing a catalyst composition, a method for hydrogenating a substrate molecule and a reaction mixture.