1595-49-9

Basic information

• Product Name: Benzenemethanol, a-(3-methyl-3-buten-1-ynyl)-
• CAS NO: 1595-49-9
• Molecular Formula: C12H12O
• Molecular Weight: 172.227
• Mol File: 1595-49-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(3-methyl-3-buten-1-ynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(3-methyl-3-buten-1-ynyl)-(1595-49-9)
• EPA Substance Registry System: Benzenemethanol, a-(3-methyl-3-buten-1-ynyl)-(1595-49-9)

Safety Data

• Hazardous Substances Data: 1595-49-9(Hazardous Substances Data)

Usage

Chemical compound

Benzenemethanol, a-(3-methyl-3-buten-1-ynyl)-

Also known as

3-Methyl-3-buten-1-yn-5-ol

Classification

Alcohol

Common uses

Organic synthesis, building block in pharmaceuticals and agrochemicals

Unique properties

Valuable intermediate in synthesis of complex organic molecules

Potential applications

Materials science, production of specialty chemicals

Upstream product

• 38341-85-4 (3-methyl-but-3-en-1-ynyl)-lithium 
• 18206-22-9 bis[2-(N,N-dimethylamino)phenyl] disulfide 
• 100-52-7 benzaldehyde 
• 594-19-4 tert.-butyl lithium 
• 107647-26-7 sulfure de (dimethylamino-2) phenyle et de (methyl-3 buten-3 yn-1) yle 
• 109-72-8 n-butyllithium 
• 78-80-8 2-methylbut-1-en-3-yne 

Downstream Products

• 1584-98-1 4-methyl-1-phenylpent-4-en-2-yn-1-one 
• 878549-71-4 4-methyl-1-phenylpent-4-en-2-yn-1-yl acetate 
• 59649-24-0 C₁₈H₁₇NO 
• 1385018-03-0 (E)-5-benzylidene-2-methyl-4-oxocyclopent-1-en-1-yl acetate 
• 1385018-21-2 (Z)-5-benzylidene-2-methyl-4-oxocyclopent-1-en-1-yl acetate 
• 26131-82-8 (+/-)-5-methyl-3-phenyl-cyclopent-2-enone 
• 878549-72-5 2-methyl-4-phenylcyclopenta-1,4-dien-1-yl acetate 

Relevant articles and documents

Gold(I)-Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)-Enyne Esters with NFSI: One-Pot Assembly of 5-Fluoro- Cyclopentenones

An efficient synthetic approach for the synthesis of 5-fluoro-cyclopentenones containing a fluorine-substituted carbon stereocenter that relies on gold(I)-catalyzed cycloisomerization and fluorination sequence of 1,3(4)-enyne esters with N-fluorbenzensulfonimide (NFSI) is described. This tandem transformation exhibited a broad substrate scope and excellent functional group compatibility, providing a novel protocol for rapid assembly 5-fluoro-cyclopentenones in good to excellent yields under mild reaction conditions. The mechanistic studies revealed that the transformation involves a gold-catalyzed cycloisomerization and electrophilic fluorination cascade to give the 5-fluoro-cyclopentenones. (Figure presented.).

Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)2]2

A class of alkenyl propargyl acetates, RCH(OAc)C≡CC(CH 3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)2]2 in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents, up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.

Preparation of siloxacyclopentene containing 1,3-dienes and their Diels-Alder reactions

A number of enynyloxy dimethyl and diisopropyl silanes have been prepared and converted into siloxacyclopentene containing 1,3-dienes via intramolecular hydrosilylation of the alkyne functional group. Diels-Alder reactions of these dienes are reported.