104046-95-9

Basic information

• Product Name: (±)-anti-1-(4-cyanophenyl)-2-phenylbut-3-en-1-ol
• CAS NO: 104046-95-9
• Molecular Weight: 249.312
• Mol File: 104046-95-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (±)-anti-1-(4-cyanophenyl)-2-phenylbut-3-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-anti-1-(4-cyanophenyl)-2-phenylbut-3-en-1-ol(104046-95-9)
• EPA Substance Registry System: (±)-anti-1-(4-cyanophenyl)-2-phenylbut-3-en-1-ol(104046-95-9)

Safety Data

• Hazardous Substances Data: 104046-95-9(Hazardous Substances Data)

Upstream product

• 2687-12-9 cinnamyl chloride 
• 105-07-7 4-cyanobenzaldehyde 
• 147609-46-9 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4392-24-9 Cinnamyl bromide 

Relevant articles and documents

Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

Lead was found to efficiently mediate the allylation reactions of carbonyl compounds with cyclic allylic halides in the presence of stoichiometric amounts of lithium chloride and a catalytic amount of GaCl3 (20 mol %), leading to the desired homoallylic alcohols in modest to high yields with excellent diastereocontrol (>99:1 syn/anti) and good functional group tolerance. In contrast, the use of either 2-pyridinecarboxaldehyde as the carbonyl substrate or (E)-cinnamyl bromide as the allylating agent produced the corresponding product with reversed diastereoselectivity (>99:1 anti/syn).

Nickel-Catalysed Allylboration of Aldehydes

A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.

Bismuth-Mediated Diastereoselective Allylation Reaction of Carbonyl Compounds with Cyclic Allylic Halides or Cinnamyl Halide

An efficient diastereoselective allylation of various carbonyl compounds with cyclic allylic halides by using commercially available bismuth powder in the presence of LiI was developed. Among all the metals screened, bismuth was found to be the best mediator for the transformation. The reactions involving various cyclic allylic halides proceeded smoothly at room temperature to produce the desired homoallylic alcohols in good to excellent yields with high diastereoselectivities (>99:1 dr). Reversed diastereoselectivity was obtained when carbonyl substrate (e. g., 2-pyridinecarboxaldehyde, glyoxylic acid) containing chelating substituent was used in the allylation reaction. In addition, the reactions involving acyclic (E)-cinnamyl bromide as substrate worked equally well with high diastereocontrol. (Figure presented.).