6625-45-2

Basic information

• Product Name: 2,6-bis(benzyloxy)benzo-1,4-quinone
• Synonyms: 2,6-bis(benzyloxy)benzo-1,4-quinone
• CAS NO: 6625-45-2
• Molecular Formula: C₂₀H₁₆O₄
• Molecular Weight: 320.33864
• Mol File: 6625-45-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 541°C at 760 mmHg
• Flash Point: 239.9°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 9.03E-12mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 2,6-bis(benzyloxy)benzo-1,4-quinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis(benzyloxy)benzo-1,4-quinone(6625-45-2)
• EPA Substance Registry System: 2,6-bis(benzyloxy)benzo-1,4-quinone(6625-45-2)

Safety Data

• Hazardous Substances Data: 6625-45-2(Hazardous Substances Data)

Usage

General Description

2,6-bis(benzyloxy)benzo-1,4-quinone, also known as bis(benzyloxy)benzoquinone, is a synthetic chemical compound with the molecular formula C20H16O4. It is a quinone derivative with a distinct yellowish-brown color and is often used as an intermediate in the synthesis of various organic compounds. This chemical is commonly utilized in the field of organic chemistry for its role as an oxidation-reduction reagent. Additionally, it has potential applications in the development of pharmaceuticals and agrochemicals due to its unique structural properties. Bis(benzyloxy)benzoquinone has drawn interest from researchers for its potential as a versatile building block in the production of new materials and as a precursor in organic synthesis. Overall, this compound holds importance as a valuable tool in the development of various organic compounds and materials.

InChI:InChI=1/C20H16O4/c21-17-11-18(23-13-15-7-3-1-4-8-15)20(22)19(12-17)24-14-16-9-5-2-6-10-16/h1-12H,13-14H2

Upstream product

• 55020-64-9 1,2,3-tris-benzyloxybenzene 
• 64-19-7 acetic acid 
• 87-66-1 2-hydroxyresorcinol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 634-94-6 1,2,3,5-tetrahydroxybenzene 
• 42528-81-4 2,6-bis-benzyloxy-benzene-1,4-diol 
• 6274-74-4 2,6-dibenzyloxy-1,4-dimethoxybenzene 
• 7499-99-2 1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone 
• 156481-55-9 1-<2-hydroxy-3,6-dimethoxy-4-(tetrahydropyran-2-yloxy)>phenylethanone 
• 20032-42-2 2,5-dimethoxyresorcinol 
• 100079-39-8 2',4'-dihydroxy-2,3',6'-trimethoxychalcone 
• 884867-35-0 C₁₈H₁₆O₅ 
• 884867-38-3 C₁₇H₁₃ClO₅ 
• 102273-92-7 7-hydroxy-5,8,2'-trimethoxyflavone 

Relevant articles and documents

Design of wogonin-inspired selective cyclin-dependent kinase 9 (CDK9) inhibitors with potent in vitro and in vivo antitumor activity

Wogonin, a natural product isolated from the plant Scutellaria baicalensis, has been shown to be a potent and selective inhibitor of CDK9. With the purpose of investigating the activity and selectivity of this chemical scaffold, several series of wogonin derivatives were prepared and screened for CDK9 inhibition and cellular antiproliferative activity. Among these compounds, the drug-like compound 51 showed potent activity against CDK9 (IC50 = 19.9 nM) and MV4-11 cell growth (IC50 = 20 nM). In addition, compound 51 showed much improved physicochemical properties, such as water solubility, compared with the parent compound wogonin. The follow-up studies showed that the compound 51 is selective toward CDK9-overexpressing cancer cells over normal cells. Preliminary mechanism studies on the anticancer effect indicated that 51 inhibited the proliferation of MV4-11 cells via caspase-dependent apoptosis. In addition, highlighted compound 51 showed significant antitumor activity in mouse acute myeloid leukemia (AML) models without producing apparent toxic effects in vivo, which gave us a new tool for further investigation of CDK9-targeted inhibitor as a potential antitumor drug especially for AML.

Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents

A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07 μM, 1.74 μM and 0.98 μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.

Total synthesis of seco-lateriflorone

A convergent strategy toward the synthesis of lateriflorone (5) is described. Our approach is based on biosynthetic considerations and draws on a sequence of prenylation, oxygenation and Claisen reactions for the construction of chromenequinone 6, and a tandem Claisen/Diels-Alder reaction cascade for the synthesis of caged tricycle 7. Union of fragments 6 and 7 led to the synthesis of seco-lateriflorone (49).