124854-74-6

Basic information

• Product Name: Butanal, 4-(phenylseleno)-
• CAS NO: 124854-74-6
• Molecular Formula: C10H12OSe
• Molecular Weight: 227.165
• Mol File: 124854-74-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Butanal, 4-(phenylseleno)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanal, 4-(phenylseleno)-(124854-74-6)
• EPA Substance Registry System: Butanal, 4-(phenylseleno)-(124854-74-6)

Safety Data

• Hazardous Substances Data: 124854-74-6(Hazardous Substances Data)

Upstream product

• 107-02-8 acrolein 
• 109-99-9 tetrahydrofuran 
• 1666-13-3 diphenyl diselenide 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 78872-18-1 5-hexenyl phenyl selenide 
• 23768-06-1 4-(phenylseleno)butanoic acid 
• 117901-60-7 δ-phenylselenobutan-1-ol 
• 74785-89-0 Methyl 4-(phenylseleno)butanoate 

Downstream Products

• 163772-72-3 8-(phenylmethoxy)-1-(phenylseleno)-5-octyn-4-ol 
• 335164-39-1 7-(phenylseleno)-1-[(triethylsilyl)oxy]-2-heptyn-4-ol 
• 344765-57-7 7-phenylselanyl-hept-1-en-4-ol 
• 951008-02-9 C₂₄H₂₈O₄Se 
• 1580535-22-3 C₂₄H₂₈O₄Se 
• 344765-56-6 6-(phenylselanyl)-1-hexen-3-ol 
• 124781-76-6 (5α,8ξ)-5,8-Dihydro-5-methoxy-7-methyl-2-phenyl-8-<3-(phenylseleno)propyl>-s-triazolo<1.2-a>pyridazine-1,3-dione 
• 124781-70-0 (1Ξ,6E)-1-Methoxy-3-methyl-7-(phenylseleno)hepta-1,3-diene 
• 124781-73-3 (E)-2-Methyl-6-(phenylseleno)-2-hexanal 
• 124781-72-2 (E)-2-Methyl-6-(phenylseleno)-2-hexen-1-ol 
• 165687-79-6 1-Benzyl-5-(2-phenylselanyl-ethyl)-3,4-dihydro-1H-pyridin-2-one 
• 165687-75-2 methyl 4-formyl-6-selenophenylhexanoate 

Relevant articles and documents

The reaction of the a-selenium stabilized copper reagents ArSeCH2Cu(CN)ZnCl

a-Arylseleno-substituted zinc and copper organometallics, in the presence of a Lewis acid, can react with aldehydes, ketones and enals with high chemoselectivity and_regioselectivity.

On the mechanism of ylide-mediated cyclopropanations: Evidence for a proton-transfer step and its effect on stereoselectivity

In this paper, we describe studies on the cyclopropanation of Michael acceptors with chiral sulfur ylides. It had previously been found that semi-stabilized sulfonium ylides (e.g., Ph-stabilized) reacted with cyclic and acyclic enones and substituted acrylates with high ee and that stabilized sulfonium ylides (e.g., ester-stabilized) reacted with cyclic enones again with high ee. The current study has focused on the reactions of stabilized sulfonium ylides with acyclic enones which unexpectedly gave low ee. Furthermore, a clear correlation of ee with ylide stability was observed in reactions with methyl vinyl ketone (MVK): ketone-stabilized ylide gave 25% ee, ester-stabilized ylide gave 46% ee, and amide-stabilized ylide gave 89% ee. It is believed that following betaine formation an unusual proton transfer step intervenes which compromises the enantioselectivity of the process. Thus, following addition of a stabilized ylide to the Michael acceptor, rapid and reversible intramolecular proton transfer within the betaine intermediate, prior to ring closure, results in an erosion of ee. Proton transfer occurred to the greatest extent with the most stabilized ylide (ketone). When the same reactions were carried out with deuterium-labeled sulfonium ylides, higher ees were observed in all cases since proton/deuteron transfer was slowed down. The competing proton transfer or direct ring-closure pathways that are open to the betaine intermediate apply not only to all sulfur ylides but potentially to all ylides. By applying this model to S-, N-, and P-ylides we have been able to rationalize the outcome of different ylide reactions bearing a variety of substituents in terms of chemo- and enantioselectivity.

The catalytic asymmetric claisen rearrangement (CAC) in natural product synthesis: Synthetic studies toward (-)-ecklonialactone B

A catalytic asymmetric Claisen rearrangement (CAC) in concert with a ring-closing metathesis (RCM) has been utilized in the enantioselective synthesis of the C10-C18 segment of ecklonialactone B. Georg Thieme Verlag Stuttgart.