14312-85-7

Basic information

• Product Name: Benzene, 1,1'-(1-methyl-1-propene-1,3-diyl)bis-, (Z)-
• Synonyms: 1,3-Diphenyl-trans-buten-(2);cis-1,3-Diphenyl-buten-(2);cis-1,3-Diphenylbuten-2
• CAS NO: 14312-85-7
• Molecular Formula: C16H16
• Molecular Weight: 208.303
• Mol File: 14312-85-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(1-methyl-1-propene-1,3-diyl)bis-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(1-methyl-1-propene-1,3-diyl)bis-, (Z)-(14312-85-7)
• EPA Substance Registry System: Benzene, 1,1'-(1-methyl-1-propene-1,3-diyl)bis-, (Z)-(14312-85-7)

Safety Data

• Hazardous Substances Data: 14312-85-7(Hazardous Substances Data)

Upstream product

• 16606-47-6 2,4-diphenylbut-1-ene 
• 29443-41-2 β-phenylethylidenehydrazine 
• 98-86-2 acetophenone 
• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 
• 98-80-6 phenylboronic acid 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 19332-07-1 2,4-diphenyl-butan-2-ol 

Relevant articles and documents

Olefin functionalization/isomerization enables stereoselective alkene synthesis

Despite tremendous efforts aimed at devising methods for stereoselective alkene synthesis, critical challenges are yet to be addressed. Direct access to a diverse range of 1-aryl(boryl)-1-methyl-functionalized tri- and tetrasubstituted trans alkenes, entities that are prevalent in many important molecules, through a catalytic manifold from readily available α-olefin substrates remains elusive. Here, we demonstrate that catalytic amounts of a non-precious N-heterocyclic carbene–Ni(I) complex in conjunction with a sterically bulky base promote site- and trans-selective union of monosubstituted olefins with a wide array of electrophilic reagents to deliver tri- and tetrasubstituted alkenes in up to 92% yield and >98% regio- and stereoselectivity. The protocol is amenable to the preparation of carbon- and heteroatom-substituted C=C bonds, providing distinct advantages over existing transformations. Utility is highlighted through concise stereoselective synthesis of biologically active compounds. [Figure not available: see fulltext.].

Ruthenium(II)-catalyzed olefination: Via carbonyl reductive cross-coupling

Natural availability of carbonyl groups offers reductive carbonyl coupling tremendous synthetic potential for efficient olefin synthesis, yet the catalytic carbonyl cross-coupling remains largely elusive. We report herein such a reaction, mediated by hydrazine under ruthenium(ii) catalysis. This method enables facile and selective cross-couplings of two unsymmetrical carbonyl compounds in either an intermolecular or intramolecular fashion. Moreover, this chemistry accommodates a variety of substrates, proceeds under mild reaction conditions with good functional group tolerance, and generates stoichiometric benign byproducts. Importantly, the coexistence of KOtBu and bidentate phosphine dmpe is vital to this transformation.

Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids

Allyl alcohols can be directly used for the palladium-catalyzed allylation of aryl- and vinyl-boronic acids without the aid of a base.