374671-36-0

Basic information

• Product Name: Br^(1-)*C₂₇H₂₁NOP⁽¹⁺⁾
• Synonyms: Br^(1-)*C₂₇H₂₁NOP⁽¹⁺⁾
• CAS NO: 374671-36-0
• Molecular Weight: 486.348
• Mol File: 374671-36-0.mol

Chemical Properties

• CAS DataBase Reference: Br^(1-)*C₂₇H₂₁NOP⁽¹⁺⁾(CAS DataBase Reference)
• NIST Chemistry Reference: Br^(1-)*C₂₇H₂₁NOP⁽¹⁺⁾(374671-36-0)
• EPA Substance Registry System: Br^(1-)*C₂₇H₂₁NOP⁽¹⁺⁾(374671-36-0)

Safety Data

• Hazardous Substances Data: 374671-36-0(Hazardous Substances Data)

Upstream product

• 20099-89-2 4-Cyanophenacyl bromide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 63072-15-1 4-[2-(triphenylphosphosphanylidene)acetyl]benzonitrile 
• 1422452-70-7 (E)-4-(3-(5-(cyclohexylmethoxy)-4-oxo-4H-chromen-3-yl)-1-hydroxyallyl)benzonitrile 
• 1422452-58-1 (E)-4-(3-(5-(cyclohexylmethoxy)-4-oxo-4H-chromen-3-yl)acryloyl)benzonitrile 

Relevant articles and documents

Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents

Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.

Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction

NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.

Enantioselective Organocatalytic Cascade Approach to Different Classes of Benzofused Acetals

A novel enantioselective organocatalytic strategy is presented for the synthesis of tetrahydrofurobenzofuran and methanobenzodioxepine natural product core structures. The strategy is based on a pair of divergent reaction pathways in which hydroxyarenes react with γ-keto-α,β-unsaturated aldehydes, catalyzed by a chiral secondary amine. One reaction pathway, which leads to chiral 5,5-fused acetals with two stereocenters—the tetrahydrofurobenzofuran scaffolds—proceeds in moderate yields and up to 96 % ee. The other reaction pathway provides 5,6-bridged methanobenzodioxepine scaffolds with three stereocenters in moderate to good yields and up to 95 % ee. The reaction is remarkable as it can proceed with catalyst loadings as low as 0.25 mol %, providing one of the highest known turnover numbers in iminium ion catalysis. Furthermore, the hemiacetal tetrahydrofurobenzofuran can undergo functionalizations including reduction, oxidation, and allylation. Finally, the effects involved in the substrate control for the divergent pathways, based on both experimental and computational studies, have been investigated. A model involving steric, electronic and stereoelectronic interactions is discussed to rationalize the observed selectivities.

Identification of novel chromenone derivatives as interleukin-5 inhibitors

A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety.

New access to trisubstitutea 3-pyrrolines under phosphine catalysis

Conjugated dienes, properly activated by electron-withdrawing groups on both ends, are shown to be suitable substrates for phosphinepromoted organocatalytic processes. Their reactions with imines, under phosphine catalysis, afford a new and efficient synthetic approach to functionalized 3-pyrrolines.