77311-61-6

Basic information

• Product Name: 3-methyl-1-phenyl-3-buten-2-ol
• Synonyms: 3-methyl-1-phenyl-3-buten-2-ol
• CAS NO: 77311-61-6
• Molecular Weight: 162.232
• Mol File: 77311-61-6.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 3-methyl-1-phenyl-3-buten-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-phenyl-3-buten-2-ol(77311-61-6)
• EPA Substance Registry System: 3-methyl-1-phenyl-3-buten-2-ol(77311-61-6)

Safety Data

• Hazardous Substances Data: 77311-61-6(Hazardous Substances Data)

Upstream product

• 557-93-7 2-bromoprop-1-ene 
• 122-78-1 phenylacetaldehyde 
• 920-39-8 isopropylmagnesium bromide 
• 78-85-3 2-methylpropenal 
• 100-39-0 benzyl bromide 
• 13291-18-4 isopropenylmagnesium bromide 
• 74669-78-6 2-(α-Benzyl-β-hydroxy-β-methylpropyloxy)tetrahydropyran 

Downstream Products

• 43043-88-5 ethyl (E)-4-methyl-6-phenylhex-4-enoate 
• 98713-65-6 Acetic acid 1-benzyl-2-methyl-allyl ester 
• 1463-04-3 (3-methylbut-3-en-1-ynyl)benzene 
• 62491-62-7 (E)-(3-methylpent-2-en-1-yl)benzene 

Relevant articles and documents

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

Palladium/Norbornene-Catalyzed ortho Aliphatic Acylation with Mixed Anhydride: Selectivity and Reactivity

A palladium/norbornene-catalyzed ortho acylation for the efficient synthesis of functionalized alkyl aryl ketones is reported. Studies on the electronic and steric properties of mixed aryl anhydrides indicated that the cross-coupling favored with the elec

Total Synthesis of Ripostatin B and Structure-Activity Relationship Studies on Ripostatin Analogs

Described is the total synthesis of the myxobacterial natural product ripostatin B and of a small number of analogs. Ripostatin B is a polyketide-derived 14-membered macrolide that acts as an inhibitor of bacterial RNA-polymerase, but is mechanistically distinct from rifamycin-derived RNA-polymerase inhibitors that are in use for tuberculosis treatment. The macrolactone ring of ripostatin B features two stereocenters and a synthetically challenging doubly skipped triene motif, with one of the double bonds being in conjugation with the ester carbonyl. Appended to the macrolactone core are an extended hydroxy-bearing phenylalkyl side chain at C13 and a carboxymethyl group at C3. The triene motif was established with high efficiency by ring-closing olefin metathesis, which proceeded in almost 80% yield. The side chain-bearing stereocenter α to the ester oxygen was formed in a Paterson aldol reaction between a methyl ketone and a β-chiral β-hydroxy aldehyde with excellent syn selectivity (dr >10:1). The total synthesis provided a blueprint for the synthesis of analogs with modifications in the C3 and C13 side chains. The C3-modified analogs showed good antibacterial activity against efflux-deficient Escherichia coli but, as ripostatin B, were inactive against Mycobacterium tuberculosis, in spite of significant in vitro inhibition of M. tuberculosis RNA-polymerase.