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(R)-2-Oxiranylanisole is a chiral organic compound characterized by the presence of an oxirane (epoxide) ring and an anisole (methoxyphenol) group. It exhibits a specific stereochemistry, with the R-configuration, which is crucial for its reactivity and applications in various chemical and pharmaceutical processes.

71031-02-2

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71031-02-2 Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-Oxiranylanisole is used as a key intermediate in the synthesis of neuroprotective small molecules and piperidinol analogs. These compounds are essential for the development of drugs targeting neurological disorders and diseases.
Used in Chemical Research:
(R)-2-Oxiranylanisole is used as a reactant in the synthesis of various chemical compounds, such as 2-substituted 3,4-dihydro-2H-1,4-benzoxazines, bicyclic azetidines, and bromoalkanes. Its unique structure allows for cyclization, ring-opening, esterification, chlorination, and intramolecular alkylation reactions, making it a versatile building block in organic chemistry.
Used in Biological Studies:
(R)-2-Oxiranylanisole is utilized as a substrate in biological studies involving Bacillus-produced enantioselective epoxide hydrolase. This enzyme plays a crucial role in the breakdown of epoxides, which are important in understanding metabolic pathways and detoxification processes in microorganisms.
Used in Anti-tuberculosis Research:
(R)-2-Oxiranylanisole is employed as a reactant in the synthesis of compounds for studies of anti-tuberculosis activity. Its unique properties make it a valuable component in the development of new drugs to combat tuberculosis, a significant global health concern.

Check Digit Verification of cas no

The CAS Registry Mumber 71031-02-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,0,3 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 71031-02:
(7*7)+(6*1)+(5*0)+(4*3)+(3*1)+(2*0)+(1*2)=72
72 % 10 = 2
So 71031-02-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O2/c1-10-8-5-3-2-4-7(8)9-6-11-9/h2-5,9H,6H2,1H3/t9-/m0/s1

71031-02-2 Well-known Company Product Price

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  • TCI America

  • (G0409)  (R)-Glycidyl Phenyl Ether  >95.0%(GC)

  • 71031-02-2

  • 1g

  • 1,280.00CNY

  • Detail
  • Aldrich

  • (29438)  (R)-2-Oxiranylanisole  ≥97.0% (sum of enantiomers, GC)

  • 71031-02-2

  • 29438-1G-F

  • 5,825.43CNY

  • Detail

71031-02-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-2-(Phenoxymethyl)oxirane

1.2 Other means of identification

Product number -
Other names (R)-2-Oxiranylanisole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71031-02-2 SDS

71031-02-2Relevant academic research and scientific papers

PRACTICAL PREPARATION OF OPTICALLY ACTIVE O-BENZYLGLYCIDOL FROM OPTICALLY ACTIVE EPICHLOROHYDRIN

Takano, Seiichi,Sekiguchi, Yoshinori,Setoh, Masaki,Yoshimitsu, Takehiko,Inomata, Kohei,et al.

, p. 1715 - 1719 (1990)

Practical preparation of optically active O-benzylglycidol has been developed starting from optically active epichlorohydrin by employing either basic or acidic conditions in the key stage.

Design, Synthesis, and Structural Analysis of Cladosporin-Based Inhibitors of Malaria Parasites

Babbar, Palak,Das, Pronay,Manickam, Yogavel,Mankad, Yash,Yadav, Swati,Parvez, Suhel,Sharma, Amit,Reddy, D. Srinivasa

, p. 1777 - 1794 (2021/05/10)

Here we have described a systematic structure activity relationship (SAR) of a set of compounds inspired from cladosporin, a tool compound that targets parasite (Plasmodium falciparum) lysyl tRNA synthetase (KRS). Four sets of analogues, synthesized based on point changes in the chemical scaffold of cladosporin and other logical modifications and hybridizations, were assessed using high throughput enzymatic and parasitic assays along with in vitro pharmacokinetics. Co-crystallization of the most potent compound in our series (CL-2) with PfKRS revealed its structural basis of enzymatic binding and potency. Further, we report that CL-2 has performed better than cladosporin in terms of metabolic stability. It thus represents a new lead for further optimization toward the development of antimalarial drugs. Collectively, along with a lead compound, the series offers insights on how even the slightest chemical modification might play an important role in enhancing or decreasing the potency of a chemical scaffold.

Discovery of a Potent and Selective Chikungunya Virus Envelope Protein Inhibitor through Computer-Aided Drug Design

álvarez, Diego E.,Battini, Leandro,Bollini, Mariela,Fidalgo, Daniela M.

, p. 1503 - 1518 (2021/06/28)

The worldwide expansion of chikungunya virus (CHIKV) into tropical and subtropical areas in the last 15 years has posed a currently unmet need for vaccines and therapeutics. The E2-E1 envelope glycoprotein complex binds receptors on the host cell and promotes membrane fusion during CHIKV entry, thus constituting an attractive target for the development of antiviral drugs. In order to identify CHIKV antivirals acting through inhibition of the envelope glycoprotein complex function, our first approach was to search for amenable druggable sites within the E2-E1 heterodimer. We identified a pocket located in the interface between E2 and E1 around the fusion loop. Then, via a structure-based virtual screening approach and in vitro assay of antiviral activity, we identified compound 7 as a specific inhibitor of CHIKV. Through a lead optimization process, we obtained compound 11 that demonstrated increased antiviral activity and low cytotoxicity (EC50 1.6 μM, CC50 56.0 μM). Molecular dynamics simulations were carried out and described a possible interaction pattern of compound 11 and the E1-E2 dimer that could be useful for further optimization. As expected from target site selection, compound 11 inhibited virus internalization during CHIKV entry. In addition, virus populations resistant to compound 11 included mutation E2-P173S, which mapped to the proposed binding pocket, and second site mutation E1-Y24H. Construction of recombinant viruses showed that these mutations conferred antiviral resistance in the parental background. Finally, compound 11 presents acceptable solubility values and is chemically and enzymatically stable in different media. Altogether, these findings uncover a suitable pocket for the design of CHIKV entry inhibitors with promising antiviral activity and pharmacological profiles.

Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives

Sarojini, Perumal,Jeyachandran, Malaichamy,Sriram, Dharmarajan,Ranganathan, Palraj,Gandhimathi

, (2021/02/26)

Novel 2-(aryloxymethyl)aziridines and 2-((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, 13C NMR, and 1H NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2-(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3-(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTB H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 μg/mL) than the standard drugs ethambutol (MIC = 1.56 μg/mL) and ciprofloxacin (MIC = 1.56 μg/mL).

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

Solís-Mu?ana, Pablo,Salam, Joanne,Ren, Chloe Z.-J.,Carr, Bronte,Whitten, Andrew E.,Warr, Gregory G.,Chen, Jack L.-Y.

supporting information, p. 3207 - 3213 (2021/06/01)

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.).

A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

Lin, Hui,Tang, Yanhong,Dong, Shuang,Lang, Ruibo,Chen, Hongge

, p. 2145 - 2151 (2020/04/17)

Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six st

Chemoselective Epoxidation of Allyloxybenzene by Hydrogen Peroxide Over MFI-Type Titanosilicate

Fujitani, Tadahiro,Hong, Dachao,Ito, Satoru,Ji, Xinyi,Kon, Yoshihiro,Nakashima, Takuya,Osuga, Ryota,Sato, Kazuhiko,Yokoi, Toshiyuki

, (2020/04/15)

The chemoselective synthesis of 2-(phenoxymethyl)oxirane from allyloxybenzene is achieved with over 90 % yield in a sustainable reaction system using titanium-substituted silicalite-1 (TS-1) as a catalyst, hydrogen peroxide (H2O2) as an oxidant, and a mixture of MeOH/MeCN as a solvent at 40 °C. No acid-catalyzed side reactions prompted by the Lewis acidity of the Ti active site in TS-1 are observed. The TS-1 catalyst can also promote the formation of oxiranes from various p-substituted allyloxybenzenes in good yields. The reaction mechanism is investigated through the reaction with other allyloxy compounds. The results, which are supported by DFT calculations, indicate that an active species of Ti peroxides formed from the reaction of TS-1 with H2O2 selectively oxidizes the allyloxybenzene to 2-(phenoxymethyl)oxirane.

Sustainable Synthesis of a Potent and Selective 5-HT7Receptor Antagonist Using a Mechanochemical Approach

Canale, Vittorio,Frisi, Valeria,Bantreil, Xavier,Lamaty, Frédéric,Zajdel, Pawe?

, p. 10958 - 10965 (2020/09/18)

A mechanochemical procedure was developed to obtain PZ-1361, a potent and selective 5-HT7 receptor antagonist, with antidepressant properties in rodents. The elaborated protocol offered several advantages over classical batch synthesis, including improvement of the overall yield (from 34% to 64%), reduction of reaction time (from 60 to 5.5 h), limitation of the use of toxic solvents, and the formation of byproducts. This approach represents a rare example of the synthesis of biologically active compounds exclusively performed using mechanochemical reactions.

Engineering a homochiral metal-organic framework based on an amino acid for enantioselective separation

Tang, Haitong,Yang, Keke,Wang, Kun-Yu,Meng, Qi,Wu, Fan,Fang, Yu,Wu, Xiang,Li, Yougui,Zhang, WenCheng,Luo, Yunfei,Zhu, Chengfeng,Zhou, Hong-Cai

, p. 9016 - 9019 (2020/08/17)

A chiral metal-organic framework possessing an open amphiphilic channel is constructed from a dicarboxylate ligand derived from an amino acid and is shown to be an efficient and recyclable chiral solid adsorbent, which is capable of separating racemic secondary alcohols, epoxides, and ibuprofen with very high enantioselectivity.

Highly regio- and enantio-selective hydrolysis of two racemic epoxides by GmEH3, a novel epoxide hydrolase from Glycine max

Zhang, Chen,Li, Chuang,Zhu, Xiu-xiu,Liu, You-yi,Zhao, Jun,Wu, Min-chen

, p. 2795 - 2803 (2020/09/01)

A novel epoxide hydrolase from Glycine max, designated GmEH3, was excavated based on the computer-aided analysis. Then, gmeh3, a GmEH3-encoding gene, was cloned and successfully expressed in E. coli Rosetta(DE3). Among the ten investigated rac-epoxides, GmEH3 possessed the highest and best complementary regioselectivities (regioselectivity coefficients, αS = 93.7% and βR = 97.2%) in the asymmetric hydrolysis of rac-m-chlorostyrene oxide (5a), and the highest enantioselectivity (enantiomeric ratio, E = 55.6) towards rac-phenyl glycidyl ether (7a). The catalytic efficiency (kcatS/KmS = 2.50 mM?1 s?1) of purified GmEH3 for (S)-5a was slightly higher than that (kcatR/KmR = 1.52 mM?1 s?1) for (R)-5a, whereas the kcat/Km (5.16 mM?1 s?1) for (S)-7a was much higher than that (0.09 mM?1 s?1) for (R)-7a. Using 200 mg/mL wet cells of E. coli/gmeh3 as the biocatalyst, the scale-up enantioconvergent hydrolysis of 150 mM rac-5a at 25 °C for 1.5 h afforded (R)-5b with 90.2% eep and 95.4% yieldp, while the kinetic resolution of 500 mM rac-7a for 2.5 h retained (R)-7a with over 99% ees and 43.2% yields. Furthermore, the sources of high regiocomplementarity of GmEH3 for (S)- and (R)-5a as well as high enantioselectivity towards rac-7a were analyzed via molecular docking (MD) simulation.

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