rel-trans-Chalcone Oxide

Base Information

• Chemical Name: rel-trans-Chalcone Oxide
• CAS No.: 7570-86-7
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.259
• UNII: U2AKU44C26
• DSSTox Substance ID: DTXSID90352520,DTXSID601032735
• Nikkaji Number: J343.142H
• Wikidata: Q82129711
• Mol file: 7570-86-7.mol

Synonyms:rel-trans-Chalcone Oxide;61840-92-4;rac-(2R,3S)-2-benzoyl-3-phenyloxirane, trans;trans-2-Benzoyl-3-phenyloxirane;NSC-402160;Chalcone Oxide, rel-trans-;SCHEMBL3839853;U2AKU44C26;DTXSID90352520;DTXSID601032735;phenyl 3-phenyloxiran-2-yl ketone;2-Benzoyl-3-phenyloxirane, trans-;Phenyl-(3-phenyl-oxiranyl)-methanone;rac-(2R,3S)-2-benzoyl-3-phenyloxirane;trans-1,3-Diphenyl-2,3-epoxyprop-1-one;trans-1,3-Diphenyl-1,2-epoxy-3-propanone;EN300-302007;rel-Phenyl[(2R,3S)-3-phenyloxiranyl]methanone;rel-Phenyl[(2R,3S)-3-phenyl-2-oxiranyl]methanone;Methanone, phenyl[(2R,3S)-3-phenyloxiranyl]-, rel-;Z2306736603;Methanone, phenyl[(2R,3S)-3-phenyl-2-oxiranyl]-, rel-

Chemical Property of rel-trans-Chalcone Oxide

Chemical Property:

• Vapor Pressure: 8.53E-06mmHg at 25°C
• Melting Point: 86-89oC(lit.)
• Boiling Point: 374.1°C at 760 mmHg
• Flash Point: 174°C
• PSA: 29.60000
• Density: 1.209g/cm³
• LogP: 3.00940
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

98%,99%, ^*data from raw suppliers

rel-trans-ChalconeOxide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(O2)C(=O)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)[C@H]2[C@@H](O2)C(=O)C3=CC=CC=C3
• Uses: rel-trans-Chalcone Oxide is a potent and selective inhibitor of cytosolic epoxide hydrolase. Also mutagenic.

Technology Process of rel-trans-Chalcone Oxide

There total 116 articles about rel-trans-Chalcone Oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1,3-diphenyl-propen-3-one (614-47-1) → trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one (5411-12-1,7570-85-6,7570-86-7,61840-92-4,61840-93-5,67381-79-7,70332-63-7)

Guidance literature:

With Cumene hydroperoxide; 4 A molecular sieve; Triphenylphosphine oxide; chiral bis[(S)-BINOL] La(III); In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1002/anie.200501676

Reference yield: 99.0%

benzalacetophenone (94-41-7) → trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one (5411-12-1,7570-85-6,7570-86-7,61840-92-4,61840-93-5,67381-79-7,70332-63-7)

Guidance literature:

With sodium hypochlorite; (6R,6"R,2R,2"R)-6,6"-dimethyldispiro[tetrahydropyran-2,2'-(2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine)-8',2"-tetrahydropyran]-9'-ium tetrafluoroborate; In water; toluene; at 0 - 20 ℃; for 16h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;

DOI:10.1016/j.tet.2015.11.058

Reference yield: 98.0%

benzaldehyde (100-52-7) + acetophenone (98-86-2) → trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one (5411-12-1,7570-85-6,7570-86-7,61840-92-4,61840-93-5,67381-79-7,70332-63-7)

Guidance literature:

benzaldehyde; acetophenone; at 60 ℃; for 3h;

With tetrabutylammomium bromide; dihydrogen peroxide; sodium hydroxide; In toluene; at 20 ℃; for 1.5h; enantioselective reaction;

DOI:10.1016/j.jcat.2015.11.020

upstream raw materials:

1,3-diphenyl-propen-3-one

cis-2,3-epoxy-1,3-diphenylpropan-1-ol

benzaldehyde

1,3-diphenyl-1-propyn-3-ol

Downstream raw materials:

(2RS,3SR)-2,3-epoxy-1,1,3-triphenyl-propan-1-ol

(2RS,3RS)-2-hydroxy-1,3-diphenyl-3-piperidino-propan-1-one

(2RS,3RS)-2-hydroxy-3-morpholino-1,3-diphenyl-propan-1-one

5-benzyl-5-phenylimidazolidine-2,4-dione

Refernces

• 1、 Shan, Haiwen,Lu, Chengrong,Zhao, Bei,Yao, Yingming. "Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands". supporting information. p. 1043 - 1053. Retrieved 2021/01/25.
• 2、 Wang, Bingyang,Lin, Jin,Sun, Qiangsheng,Xia, Chungu,Sun, Wei. "Efficient Aliphatic C-H Oxidation and C═C Epoxidation Catalyzed by Porous Organic Polymer-Supported Single-Site Manganese Catalysts". . p. 10964 - 10973. Retrieved 2021/09/08.