893-01-6

Basic information

• Product Name: tenylidone
• Synonyms: tenylidone;2,6-Bis(2-thienylmethylene)cyclohexanone
• CAS NO: 893-01-6
• Molecular Formula: C₁₆H₁₄OS₂
• Molecular Weight: 286.41
• EINECS: 212-969-9
• Mol File: 893-01-6.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 488.2°C at 760 mmHg
• Flash Point: 249.1°C
• Appearance: /
• Density: 1.316g/cm³
• Vapor Pressure: 1.11E-09mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: tenylidone(CAS DataBase Reference)
• NIST Chemistry Reference: tenylidone(893-01-6)
• EPA Substance Registry System: tenylidone(893-01-6)

Safety Data

• Hazardous Substances Data: 893-01-6(Hazardous Substances Data)

Usage

Originator

Tenylidone,JINGTIAN PORTLINK

Manufacturing Process

2,6-Bis(2-thenylidene)cyclohexanone was obtained by condensation of 1 mol cyclohexanone with 2 mol 2-formylthiophene.

InChI:InChI=1/C16H14OS2/c17-16-12(10-14-6-2-8-18-14)4-1-5-13(16)11-15-7-3-9-19-15/h2-3,6-11H,1,4-5H2/b12-10+,13-11+

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 108-94-1 cyclohexanone 

Relevant articles and documents

Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX

Inflammation is a pathophysiological condition which progresses through the prostaglandin (PG) and leukotriene (LT) pathways channelized by the enzymes COX/mPGES1 and 5-LOX respectively. Diarylidenecyclohexanone (DAC) derivatives (Ia-j, IIa-c, IIIa and IVa) were synthesized, characterized and screened for their in vitro anti-inflammatory activity via inhibition of 5-LOX and COX-2/mPGES1 enzymes. Compound Ic inhibited PGE2 production exhibiting an IC50 of 6.7 ± 0.19 μM, comparable to the standard inhibitor, licofelone (IC50 of 5.4 ± 0.02 μM). Compounds Ie and Ig showed maximum in vitro inhibitory activity against 5-LOX, exhibiting an IC50 of 1.4 ± 0.1 μM and 1.5 ± 0.13 μM, respectively, and these are comparable to that of the standard drug, zileuton (IC50 = 1.2 ± 0.11 μM). Ie and Ig do not possess radical scavenging properties and may not be disrupting the redox cycle of the enzyme. Hence they may be inhibiting the enzyme by a competitive mode. One of the compounds in the DAC series (IIc) containing a heterocyclic thienyl ring inhibited all the three enzymes. It inhibited 5-LOX and COX-2/mPGES1 with an IC50 of 1.8 ± 0.12 μM and 7.5 ± 0.4 μM respectively. An RT-PCR based mRNA expression study highlighted that Ic predominantly inhibited the expression of COX-2 rather than mPGES1. No toxicity towards the HeLa cell line indicated that the DACs could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs as anti-inflammatory agents.

Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines

A Ag/P-stereogenic phosphine-complex-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with electron-deficient olefins is reported. In this reaction, highly functionalized pyrrolines with a spiro-quaternary stereogenic center were obtained in good yields (up to 99%) with excellent levels of diastereo-(up to >20:1 dr) and enantioselectivities (up to >99% ee). The chirality of adducts was controlled predominantly by the P-stereogenic phosphines.

Preparation method for synthesizing photosensitive compound through Claisen-Schmidt reaction

The invention provides a preparation method for synthesizing a photosensitive compound through a Claisen-Schmidt reaction. An aldehyde free of alpha-H and a ketone containing alpha-H are selected to be synthesized to obtain the product alpha, beta-unsaturated aldehyde ketone. The preparation method is simple in condition and mild in reaction. The prepared photosensitive compound serving as a hydrogen abstraction type photoinitiator is long in wave length and small in consumption, and has a good initiation effect on monomer PEFDA without adding initiation auxiliaries. Under an ultraviolet lamp,the absorption wavelength is subjected to red shift from 450 to 500 and finally subjected to blue shift to 400 or below. The photosensitive compound has an AIE effect.