75478-63-6

Basic information

• Product Name: (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol
• Synonyms: (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol
• CAS NO: 75478-63-6
• Molecular Weight: 252.401
• Mol File: 75478-63-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol(75478-63-6)
• EPA Substance Registry System: (E)-1-(1,3-dithian-2-yl)-3-phenylprop-2-en-1-ol(75478-63-6)

Safety Data

• Hazardous Substances Data: 75478-63-6(Hazardous Substances Data)

Upstream product

• 505-23-7 1,3 dithiane 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 13411-42-2 2-(trimethylsilyl)-1,3-dithiane 
• 36049-90-8 2-lithio-1,3-dithiane 

Relevant articles and documents

Bu4N+ alkoxide-initiated/autocatalytic addition reactions with organotrimethylsilanes

The use of Me3SiO-/Bu4N+ as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.

An efficient photo-SET-induced cleavage of dithiane-carbonyl adducts and its relevance to the development of photoremovable protecting groups for ketones and aldehydes

Irradiation of dithiane-aldehyde/ketone adducts in the presence of benzophenone leads to C-C bond cleavage regenerating the carbonyl compounds. It is established that the mechanism of this reaction involves photochemically induced single electron transfer from the dithiane moiety to the excited molecule of ET-photosensitizer, accompanied by mesolytic C-C cleavage in the generated cation-radical, which is assisted by the anion- radical of benzophenone. This mechanism is confirmed by a Hammett plot study of the cleavage in the dithiane adducts of substituted aromatic aldehydes and a deuterium kinetic isotope effect study. Ab initio computations at UHF/6- 31G* and MP2/6-31G* levels of theory in conjunction with self-consistent reaction field (self-consistent isodensity-polarized continuum model), to account for the solvent effect, also support the experimental findings. The reaction is most efficient for protection of aromatic aldehydes and ketones and aliphatic ketones, and is a novel method for protecting carbonyl functionalities with a photoremovable group.

1,4-ADDITION OF LITHIATED DERIVATIVES FROM 1,3-DITHIANES TO Α-UNSATURATED ALDEHYDES: A WAY TO Δ-CARBONYL ALDEHYDES

1,4-Addition of the lithiated derivatives of the 1,3-dithiane and 2-phenyl-1,3-dithiane on α-unsaturated aldehydes is performed in THF-HMPA ; this reaction could be an interesting way to δ-carbonyl aldehydes.