717123-42-7

Basic information

• Product Name: 2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethan-1-ol
• Synonyms: 2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethan-1-ol
• CAS NO: 717123-42-7
• Molecular Weight: 270.328
• Mol File: 717123-42-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethan-1-ol(717123-42-7)
• EPA Substance Registry System: 2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethan-1-ol(717123-42-7)

Safety Data

• Hazardous Substances Data: 717123-42-7(Hazardous Substances Data)

Upstream product

• 119-61-9 benzophenone 
• 3068-00-6 D,L-1,2,4-butanetriol 
• 2235-01-0 dimethoxydiphenylmethane 

Downstream Products

• 717123-45-0 2-(2,2-diphenyl-1,3-dioxolan-4-yl)ethyl tosylate 
• 717123-46-1 4-(2-azidoethyl)-2,2-diphenyl-1,3-dioxolane 

Relevant articles and documents

1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity

A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and α1 adrenoceptors. The compounds with greater affinity were selected for further functional studies. N-((2,2-diphenyl-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD2 = 9.22, %Emax = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potential use in the treatment of chronic pain.

Synthesis and NMDA-receptor affinity of ring and side chain homologous dexoxadrol derivatives.

The regioselectivity during transacetalization of benzophenone dimethyl acetal (4) with butane-1, 2, 4-triol (5) is controlled by the reaction conditions. Thermo-dynamic control leads predominantly to the 1, 3-dioxolane 6 whereas kinetic control favors the six-membered acetal 7. The amines 2a-e and 3a-e are synthesized from the alcohols 6 and 7 and are investigated in receptor binding studies with radioligands for their affinity to the phencyclidine binding site of the NMDA-receptor. In both series the primary amines 2a and 3a show the highest NMDA-receptor affinity (2a: Ki=3.38 microM; 3a: Ki=1.45 microM). The NMDA receptor slightly prefers the 1, 3-dioxane derivatives 3a and 3b compared to 2a and 2b (factor 2-3). Low interactions of the amines 3a and 3b with various receptor and reuptake systems indicate selectivity for the NMDA receptor. Surprisingly, the piperidine derivative 2e binds with high affinity at sigma1-receptors and, therefore, represents a novel lead compound for high affinity sigma1-receptor ligands.