2,2-Dimethoxy-2-phenylacetophenone

• CAT Number: R050449
• CAS Number: 24650-42-8
• Molecular Formula: C16H16O3
• Molecular Weight: 256.301
• Purity: ≥95%
• Synonyms: 2,2-Dimethoxy-1,2-diphenylethanone; Benzil Dimethyl Acetal; 1,2-Diphenyl-2,2-dimethoxyethanone; 2,2-Dimethoxy-1,2-diphenyl-1-ethanone; 2-Phenyl-2,2-dimethoxyacetophenone; Aronix C 101; BDK; Benzil Dimethyl Ketal; Benzoin Dimethyl Ether; C 101; DMPA
• Storage: Store at -20°C
• IUPAC Name: 2,2-dimethoxy-1,2-diphenylethanone
• InChI: InChI=1S/C16H16O3/c1-18-16(19-2,14-11-7-4-8-12-14)15(17)13-9-5-3-6-10-13/h3-12H,1-2H3
• InChIKey: KWVGIHKZDCUPEU-UHFFFAOYSA-N
• SMILES: COC(C1=CC=CC=C1)(C(=O)C2=CC=CC=C2)OC

2,2-Dimethoxy-2-phenylacetophenone (CAS 24650-42-8) is a photoinitiator, which is used to initialise radical polymerization in the preparation of acrylate polymers.Under the influence of light the molecule will form radicals which initiate the radical polymerization. It can also be used as an initiator in the process of making an integrated circuit.

 

Reference

1.Liao KC, Hogen-Esch T, Richmond FJ, Marcu L, Clifton W, Loeb GE (2008). "Percutaneous fiber-optic sensor for chronic glucose monitoring in vivo". Biosens Bioelectron. 23 (10): 1458–65

2.J Vis Exp. 2018 Aug 1;(138):57356. doi: 10.3791/57356.Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation.Shi X(1), Liu Y(1), Zhao R(1), Li Z(2).

 

Here, we describe a detailed protocol for the preparation of thioether-tethered peptides using on-resin intramolecular/intermolecular thiol-ene hydrothiolation. In addition, this protocol describes the preparation of vinyl-sulfide-tethered peptides using in-solution intramolecular thiol-yne hydrothiolation between amino acids that possess alkene/alkyne side chains and cysteine residues at i, i+4 positions. Linear peptides were synthesized using a standard Fmoc-based solid-phase peptide synthesis (SPPS). Thiol-ene hydrothiolation is carried out using either an intramolecular thio-ene reaction or an intermolecular thio-ene reaction, depending on the peptide length. In this research, an intramolecular thio-ene reaction is carried out in the case of shorter peptides using on-resin deprotection of the trityl groups of cysteine residues following the complete synthesis of the linear peptide. The resin is then set to UV irradiation using photoinitiator 4-methoxyacetophenone (MAP) and 2-hydroxy-1-[4-(2-hydroxyethoxy)-phenyl]-2-methyl-1-propanone (MMP). The intermolecular thiol-ene reaction is carried out by dissolving Fmoc-Cys-OH in an N,N-dimethylformamide (DMF) solvent. This is then reacted with the peptide using the alkene-bearing residue on resin. After that, the macrolactamization is carried out using benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBop), 1-hydroxybenzotriazole (HoBt), and 4-Methylmorpholine (NMM) as activation reagents on the resin. Following the macrolactamization, the peptide synthesis is continued using standard SPPS. In the case of the thio-yne hydrothiolation, the linear peptide is cleaved from the resin, dried, and subsequently dissolved in degassed DMF. This is then irradiated using UV light with photoinitiator 2,2-dimethoxy-2-phenylacetophenone (DMPA). Following the reaction, DMF is evaporated and the crude residue is precipitated and purified using high-performance liquid chromatography (HPLC). These methods could function to simplify the generation of thioether-tethered cyclic peptides due to the use of the thio-ene/yne click chemistry that possesses superior functional group tolerance and good yield. The introduction of thioether bonds into peptides takes advantage of the nucleophilic nature of cysteine residues and is redox-inert relative to disulfide bonds.

 

3. Langmuir. 2019 Apr 2;35(13):4534-4539. doi: 10.1021/acs.langmuir.9b00230. Epub 2019 Mar 18.Photocurable Urushiol Analogues Bearing Methacryloxy-Containing Side chains.Watanabe H(1), Takahashi M(1), Kihara H(1), Yoshida M(1).

 

Photocurable urushiol analogues were synthesized using eugenol (an ingredient of clove oil) as the starting material. Photo-induced radical polymerization with 2,2-dimethoxy-2-phenylacetophenone as a photo-initiator took place in the film prepared from the urushiol analogue-bearing methacryloxy groups at the ends of their side chains. Successful polymerization was confirmed by infrared spectroscopy measurements of the film before and after photo-irradiation. Strain-induced elastic buckling instability for mechanical measurement tests revealed that the Young's moduli of the photo-irradiated samples were 4-5 times higher than the films without photo-irradiation. This was attributed to the formation of a highly cross-linked structure through polymerization of the methacrylic moieties and oxidative polymerization of the catechol moieties. Photo-induced surface texturing was also performed for the films prepared on a substrate using a photomask. Negative-tone patterns were successfully obtained after development by soaking in cyclohexanone over several minutes. The preparation of such patterned surfaces was of particular relevance as the obtained surface can serve as a scaffold for cell adhesion, protein immobilization, and the immobilization of other chemicals with spatial  disposition.