62249-80-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-VINYL-OXIRANE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of complex organic molecules that can be utilized in the development of new drugs and medicinal compounds.
Used in Pesticide Production:
In the agricultural sector, (S)-2-VINYL-OXIRANE serves as a key intermediate in the production of certain pesticides. Its reactivity enables the formation of bioactive molecules that can be used to control pests and protect crops.
Used in Polymer Synthesis:
(S)-2-VINYL-OXIRANE is utilized in the synthesis of polymers due to its ability to participate in polymerization reactions. This makes it a valuable component in the development of new types of plastics and other polymer-based materials.
Used in Resin Production:
(S)-2-VINYL-OXIRANE is also used in the production of resins, where its properties contribute to the formation of resinous materials with specific characteristics required for various applications.
Used as a Stabilizer in Plastics:
(S)-2-VINYL-OXIRANE functions as a stabilizer in plastics, helping to maintain the integrity and performance of plastic materials over time.
Used in Adhesive Manufacturing:
In the manufacturing of adhesives, (S)-2-VINYL-OXIRANE is used to enhance the bonding properties and durability of adhesive products.
Used in Research and Industrial Processes:
Due to its reactivity, (S)-2-VINYL-OXIRANE has potential applications in research and various industrial processes, where it can be employed to explore new chemical reactions and develop innovative products.
It is crucial to handle and use (S)-2-VINYL-OXIRANE with care, as it may present risks to human health and the environment if not managed properly.

Upstream product

• 56536-49-3 (2S)-2-chlorobutan-1-ol 
• 930-22-3 epoxybutene 
• 143-33-9 sodium cyanide 
• 133095-74-6 (S)-2-hydroxy-3-buten-1-yl p-tosylate 
• 106-99-0 buta-1,3-diene 
• 108269-47-2 (R)-2-bromobutyl butyrate 
• 70379-72-5 (R)-2-acetoxy-1-bromobutane 

Downstream Products

• 123093-78-7 4-Aethoxy-2-buten-1-ol 
• 1085493-00-0 C₂₀H₂₉NO₄ 
• 1085493-02-2 C₂₀H₂₉NO₄ 
• 1262870-74-5 (S)-2-[(E,4S,6S)-4,6-bis(4-methoxybenzyloxy)-8-phenyloct-1-enyl]oxirane 
• 821-11-4 1,4-butenediol 
• 62214-39-5 (2S)-but-3-ene-1,2-diol 
• 86106-09-4 (R)-(+)-3,4-dihydroxy-1-butene 

Relevant academic research and scientific papers

An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst

An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).

Discovery of a Cyclic Choline Analog That Inhibits Anaerobic Choline Metabolism by Human Gut Bacteria

The anaerobic conversion of choline to trimethylamine (TMA) by the human gut microbiota has been linked to multiple human diseases. The potential impact of this microbial metabolic activity on host health has inspired multiple efforts to identify small molecule inhibitors. Here, we use information about the structure and mechanism of the bacterial enzyme choline TMA-lyase (CutC) to develop a cyclic choline analog that inhibits the conversion of choline to TMA in bacterial whole cells and in a complex gut microbial community. In vitro biochemical assays and a crystal structure suggest that this analog is a competitive, mechanism-based inhibitor. This work demonstrates the utility of structure-based design to access inhibitors of radical enzymes from the human gut microbiota.

ISOSELECTIVE POLYMERIZATION OF EPOXIDES

The present invention provides novel bimetallic complexes and methods of using the same in the isoselective polymerization of epoxides. The invention also provides methods of kinetic resolution of epoxides. The invention further provides polyethers with high enantiomeric excess that are useful in applications ranging from consumer goods to materials.

Asymmetric synthesis of the ABCD ring system of daphnilactone B via a tandem, double intramolecular, [4+2]/[3+2] cycloaddition strategy

An asymmetric synthesis of the ABCD ring system of daphnilactone B is described. The synthesis features a tandem, double intramolecular, [4+2]/[3+2] cycloaddition of a highly functionalized, enantiomerically enriched nitroalkene to generate a pentacyclic nitroso acetal. The cycloaddition establishes six contiguous stereogenic centers including the critical CD ring junction that bears two quaternary stereogenic centers. Hydrogenolysis of the nitroso acetal followed by amide reduction and cyclization provided the AB rings. The methyl substituent on the A ring was installed in the correct configuration via hydrogenation of an exocyclic olefin in the final step.. The Japan Institute of Heterocyclic Chemistry.

"Cassette" in situ enzymatic screening identifies complementary chiral scaffolds for hydrolytic kinetic resolution across a range of epoxides

(Figure Presented) Put the cassette in: An in situ enzymatic screen can give real-time estimates of the sense and magnitude of enantioselectivity across more than one substrate. Screening identified CoIII-salen catalysts with β-pinene- and α-naphthylalanine-derived chiral scaffolds with broad, yet complementary, substrate specificities. ADH = alcohol dehydrogenase, HL = horse liver, LK = Lactobacillus kefir, salen = (salicylidene) ethylenediamine.

Enantioselective ring opening of epoxides with cyanide catalysed by halohydrin dehalogenases: A new approach to non-racemic β-hydroxy nitriles

Halohydrin dehalogenases (HheA, HheB and HheC) were found to efficiently catalyse a carbon-carbon bond forming reaction between terminal aliphatic epoxides and cyanide, yielding β-hydroxy nitriles. With all three enzymes nucleophilic ring opening of epoxi

The preparation of enantiomerically pure 3,4-epoxy-1-butene and 3-butene-1,2-diol

Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxytosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis. Georg Thieme Verlag Stuttgart.

Extensively stereodiversified scaffolds for use in diversity-oriented library synthesis

Figure presented The syntheses of stereodiverse libraries of 12 and 19 are reported, where each asterisk represents an independently varied stereocenter. These scaffolds provide additional templates for investigations of geometric diversity in library syn

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.