40022-83-1

Basic information

• Product Name: DL-2-phenyl-3-butene-2-yl acetate
• Synonyms: DL-2-phenyl-3-butene-2-yl acetate
• CAS NO: 40022-83-1
• Molecular Weight: 190.242
• Mol File: 40022-83-1.mol

Chemical Properties

• CAS DataBase Reference: DL-2-phenyl-3-butene-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-phenyl-3-butene-2-yl acetate(40022-83-1)
• EPA Substance Registry System: DL-2-phenyl-3-butene-2-yl acetate(40022-83-1)

Safety Data

• Hazardous Substances Data: 40022-83-1(Hazardous Substances Data)

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 108-24-7 acetic anhydride 
• 98-86-2 acetophenone 
• 6051-52-1 2-phenylbut-3-en-2-ol 

Downstream Products

• 36617-88-6 (R)-3-phenyl-1-butene 
• 58717-85-4 (S)-3-phenyl-1-butene 
• 20883-16-3 β-methylcinnamyl acetate 
• 1310827-42-9 dimethyl 2-methyl-2-(2-phenylbut-3-en-2-yl)malonate 
• 1440956-77-3 N-benzyl-2-phenylbut-3-en-2-amine 

Relevant articles and documents

Continuous flow-processing of organometallic reagents using an advanced peristaltic pumping system and the telescoped flow synthesis of (E/Z)-tamoxifen

A new enabling technology for the pumping of organometallic reagents such as n-butyllithium, Grignard reagents, and DIBAL-H is reported, which utilises a newly developed, chemically resistant, peristaltic pumping system. Several representative examples of its use in common transformations using these reagents, including metal-halogen exchange, addition, addition-elimination, conjugate addition, and partial reduction, are reported along with examples of telescoping of the anionic reaction products. This platform allows for truly continuous pumping of these highly reactive substances (and examples are demonstrated over periods of several hours) to generate multigram quantities of products. This work culminates in an approach to the telescoped synthesis of (E/Z)-tamoxifen using continuous-flow organometallic reagent-mediated transformations.

[(NHC)Au1]-catalyzed rearrangement of allylic acetates

Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.