4638-04-4

Usage

Uses

Used in Adhesives and Sealants:
[(o-allylphenoxy)methyl]oxirane is used as a crosslinking agent in the production of adhesives and sealants. Its ability to form strong covalent bonds enhances the durability and performance of these products.
Used in Coatings:
[(o-allylphenoxy)methyl]oxirane is also utilized in the manufacturing of coatings, where its crosslinking properties contribute to the formation of a robust and long-lasting protective layer.
Used in Epoxy Resins:
[(o-allylphenoxy)methyl]oxirane serves as a crosslinking agent in epoxy resins, improving their mechanical properties and chemical resistance.
Used as a Chemical Intermediate:
It is employed as a chemical intermediate in the synthesis of other organic compounds, showcasing its versatility in the chemical industry.
Used in Polymer Synthesis:
[(o-allylphenoxy)methyl]oxirane acts as a building block in the synthesis of polymers, contributing to the development of new materials with specific properties.
Used as a Reactive Diluent:
In epoxy formulations, [(o-allylphenoxy)methyl]oxirane is used as a reactive diluent, which helps in reducing the viscosity of the resin and improving its processability.
Used in Pharmaceuticals and Agrochemicals:
Additionally, [(o-allylphenoxy)methyl]oxirane has applications in the manufacturing of pharmaceuticals and agrochemicals, where its reactive nature is harnessed for the development of various products.
It is important to handle [(o-allylphenoxy)methyl]oxirane with care, as it may cause skin and respiratory irritation, and exposure to high concentrations can be harmful.

InChI:InChI=1/C12H14O2/c1-2-5-10-6-3-4-7-12(10)14-9-11-8-13-11/h2-4,6-7,11H,1,5,8-9H2

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 1745-81-9 o-Allylphenol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 1746-13-0 allyl phenyl ether 
• 106-89-8 epichlorohydrin 
• 49716-04-3 1-(2-allyl-phenoxy)-3-chloro-propan-2-ol 

Downstream Products

• 77216-31-0 1-[[2-(3-indolyl)-1,1-dimethylethyl]amino]-3-[2-(2-propenyl)phenoxy]-2-propanol 
• 97879-21-5 N⁸-<3-(o-allylphenoxy)-2-hydroxypropyl>-(Z)-1,8-diamino-p-menthane 
• 97879-22-6 N¹-<3-(o-allylphenoxy)-2-hydroxypropyl>-(Z)-1,8-diamino-p-menthane 
• 97879-20-4 N¹,N⁸-bis<3-(o-allylphenoxy)-2-hydroxypropyl>-(Z)-1,8-diamino-p-menthane 
• 105996-36-9 dl-1-(2-Allylphenoxy)-2-hydroxy-3-dimethylaminopropane 
• 97879-27-1 N⁸-<3-(o-allylphenoxy)-2-hydroxypropyl>-N¹-(bromoacetyl)-(Z)-1,8-diamino-p-menthane 
• 97879-26-0 N¹-<3-(o-allylphenoxy)-2-hydroxypropyl>-N⁸-(bromoacetyl)-(Z)-1,8-diamino-p-menthane 
• 97879-29-3 N⁸-<3-(o-allylphenoxy)-2-hydroxypropyl>-N¹-(bromoacetyl)-(E)-1,8-diamino-p-menthane 
• 97879-28-2 N¹-<3-(o-allylphenoxy)-2-hydroxypropyl>-N⁸-(bromoacetyl)-(E)-1,8-diamino-p-menthane 
• 97879-23-7 N¹,N⁸-bis<3-(o-allylphenoxy)-2-hydroxypropyl>-(E)-1,8-diamino-p-menthane 
• 97879-24-8 N⁸-<3-(o-allylphenoxy)-2-hydroxypropyl>-(E)-1,8-diamino-p-menthane 
• 97879-25-9 N¹-<3-(o-allylphenoxy)-2-hydroxypropyl>-(E)-1,8-diamino-p-menthane 
• 70580-01-7 4-{2-[3-(2-Allyl-phenoxy)-2-hydroxy-propylamino]-ethyl}-phenol 
• 56215-84-0 1-(2-Allyl-phenoxy)-3-(3-ethylsulfanyl-propylamino)-propan-2-ol 

Relevant academic research and scientific papers

Controlling cellular distribution of drugs with permeability modifying moieties

Phenotypic screening provides compounds with very limited target cellular localization data. In order to select the most appropriate target identification methods, determining if a compound acts at the cell-surface or intracellularly can be very valuable. In addition, controlling cell-permeability of targeted therapeutics such as antibody-drug conjugates (ADCs) and targeted nanoparticle formulations can reduce toxicity from extracellular release of drug in undesired tissues or direct activity in bystander cells. By incorporating highly polar, anionic moieties via short polyethylene glycol linkers into compounds with known intracellular, and cell-surface targets, we have been able to correlate the cellular activity of compounds with their subcellular site of action. For compounds with nuclear (Brd, PARP) or cytosolic (dasatinib, NAMPT) targets, addition of the permeability modifying group (small sulfonic acid, polycarboxylic acid, or a polysulfonated fluorescent dye) results in near complete loss of biological activity in cell-based assays. For cell-surface targets (H3, 5HT1A, β2AR) significant activity was maintained for all conjugates, but the results were more nuanced in that the modifiers impacted binding/activity of the resulting conjugates. Taken together, these results demonstrate that small anionic compounds can be used to control cell-permeability independent of on-target activity and should find utility in guiding target deconvolution studies and controlling drug distribution of targeted therapeutics.

Continuous flow upgrading of glycerol toward oxiranes and active pharmaceutical ingredients thereof

A robust continuous flow procedure for the transformation of bio-based glycerol into high value-added oxiranes (epichlorohydrin and glycidol) is presented. The flow procedure features a central hydrochlorination/dechlorination sequence and provides economically and environmentally favorable conditions involving an organocatalyst and aqueous solutions of hydrochloric acid and sodium hydroxide. Pimelic acid (10 mol%) shows an exceptional catalytic activity (>99% conversion of glycerol, a high selectivity toward 1,3-dichloro-2-propanol and 81% cumulated yield toward intermediate chlorohydrins) for the hydrochlorination of glycerol (140 °C) with 36 wt% aqueous HCl. These conditions are validated on a sample of crude bio-based glycerol. The dechlorination step is effective (quantitative conversion based on glycerol) with concentrated aqueous sodium hydroxide (20 °C) and can be directly concatenated to the hydrochlorination step, hence providing a ca. 2:3 separable mixture of glycidol and epichlorohydrin (74% cumulated yield). An in-line membrane separation unit is included downstream, providing usable streams of epichlorohydrin (in MTBE, with an optional concentrator) and glycidol (in water). The scalability of the dechlorination step is then assessed in a commercial pilot-scale continuous flow reactor. Next, bio-based epichlorohydrin is further utilized for the continuous flow preparation of β-amino alcohol active pharmaceutical ingredients including propranolol (hypertension, WHO essential), naftopidil (prostatic hyperplasia) and alprenolol (angina pectoris) within a concatenable two-step procedure using a FDA class 3 solvent (DMSO). This work provides the first example of direct upgrading of bio-based glycerol into high value-added pharmaceuticals under continuous flow conditions.

EPOXY AND ALKOXY SILYL GROUP-CONTAINING SILSESQUIOXANE AND COMPOSITION THEREOF

A silicon compound is described, being obtained by a hydrosilylation reaction of the following compound (a), compound (b) and compound (c). Compound (a) is a silsesquioxane derivative having two or more SiH in one molecule. Compound (b) is a compound having, in one molecule, epoxy and/or oxetanyl and an alkenyl having a carbon number of 2 to 18. Compound (c) is a compound having, in one molecule, an alkoxysilyl and an alkenyl having a carbon number of 2 to 18.

Continuous and convergent access to vicinyl amino alcohols

Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.

Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(iii)-salen complexes: A practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: Computational rationale for enantioselectivity

A series of chiral polymeric Co(iii)-salen complexes based on a number of achiral and chiral linkers were synthesized and their catalytic performances were assessed in the asymmetric hydrolytic kinetic resolution of terminal epoxides. The effects of the linker were judiciously studied and it was found that in the case of the chiral BINOL-based polymeric salen complex 1, there was an enrichment in catalyst reactivity and enantioselectivity of the unreacted epoxide, particularly in the case of short as well as long chain aliphatic epoxides. Good isolated yields of the unreacted epoxide (up to 46% compared to 50% theoretical yield) along with high enantioselectivity (up to 99%) were obtained in most cases using catalyst 1. Further studies showed that catalyst 1 could retain its catalytic activity for six cycles under the present reaction conditions without any significant loss in activity or enantioselectivity. To show the practical applicability of the above synthesized catalyst we have synthesised some potent chiral β-blockers in moderate yield and high enantioselectivity using complex 1. The DFT (M06-L/6-31+G??//ONIOM(B3LYP/6-31G?:STO-3G)) calculations revealed that the chiral BINOL linker influences the enantioselectivity achieved with Co(iii)-salen complexes. Further, the transition state calculations show that the R-BINOL linker with the (S,S)-Co(iii)-salen complex is energetically preferred over the corresponding S-BINOL linker with the (S,S)-Co(iii)-salen complex for the HKR of 1,2-epoxyhexane. The role of non-covalent C-H?π interactions and steric effects has been discussed to control the HKR reaction of 1,2-epoxyhexane.

A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors

Microtuning of the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward bulky substrates. Hot pockets: Microtuning of the enzyme active pocket gives a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots, and enhanced activity toward bulky substrates was found.

A vHTS approach for the identification of β-adrenoceptor ligands

Using a vHTS based on a pharmacophore alignment on known β3-adrenoceptor ligands, a set of intriguing β-adrenoceptor ligands was identified, optimization of which resulted in a selective and potent human β2-AR antagonist.

Thienopyrimidines as β3-adrenoceptor agonists: Hit-to-lead optimization

Resulting from a vHTS based on a pharmacophore alignment on known β3-adrenoceptor ligands, an aryloxypropanolamine scaffold comprising a thienopyrimidine moiety was further optimized as a human β3-AR agonist, yielding a lead compound with an excellent cellular activity of EC50 = 20 pM, selectivity over hβ1- and hβ2-adrenoceptors and a promising safety profile.

Titanocene(III) mediated radical cyclizations of epoxides for the synthesis of medium-sized cyclic ethers

Titanocene(III) chloride (Cp2TiCl) mediated 7-exo and 8-endo radical cyclizations of epoxides towards the synthesis of 7- and 8-membered cyclic ethers have been described. Titanocene(III) chloride was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and activated zinc dust in THF.

Titanocene(III) mediated 8-endo radical cyclizations for the synthesis of eight-membered cyclic ethers

Titanocene(III) chloride (Cp2TiCl) mediated 8-endo radical cyclizations towards the synthesis of eight-membered cyclic ethers have been described. Titanocene(III) chloride was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and activated zinc dust in THF.