121522-26-7

Basic information

• Product Name: 3-Butyn-2-ol, 4-(trimethylsilyl)-, (R)-
• CAS NO: 121522-26-7
• Molecular Formula: C7H14OSi
• Molecular Weight: 142.273
• Mol File: 121522-26-7.mol
• Article Data: 57

Chemical Properties

• CAS DataBase Reference: 3-Butyn-2-ol, 4-(trimethylsilyl)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butyn-2-ol, 4-(trimethylsilyl)-, (R)-(121522-26-7)
• EPA Substance Registry System: 3-Butyn-2-ol, 4-(trimethylsilyl)-, (R)-(121522-26-7)

Safety Data

• Hazardous Substances Data: 121522-26-7(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 2028-63-9 but-3-yn-2-ol 
• 109-72-8 n-butyllithium 
• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 
• 75-07-0 acetaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 74-88-4 methyl iodide 
• 5930-98-3 4-trimethylsilyl-3-butyn-2-one 
• 103253-60-7 4-trimethylsilyl-3-butyn-2-ol 
• 344580-04-7 2,2,2-trifluoroethyl 2,2,3,3-tetrahydroperfluoroundecanoate 
• 103620-64-0 1-Trimethylsilanyl-3-trimethylsilanyloxy-but-1-yne 
• 129571-78-4 (R)-4-trimethylsilyl-3-butyn-2-yl acetate 
• 917-64-6 methyl magnesium iodide 
• 2975-46-4 3-(trimethylsilyl)prop-2-yn-1-al 

Downstream Products

• 129571-78-4 (R)-4-trimethylsilyl-3-butyn-2-yl acetate 
• 6999-19-5 (S)-4-trimethylsilyl-3-butyn-2-ol 
• 146514-00-3 4-trimethylsilylbut-3-yn-2-yl benzoate 
• 42969-65-3 (R)-(+)-3-butyn-2-ol 
• 1026984-69-9 C₂₁H₂₃NO₅Si 
• 111887-18-4 4-(4-methoxyphenyl)but-3-yn-2-ol 
• 1182221-95-9 methyl (2S,5R,6S)-2-ethyl-5-((4-methoxybenzyloxy)methyl)-2,6-dimethyl-3-oxo-8-(trimethylsilyl)oct-7-ynoate 

Relevant articles and documents

Propargylation of CoQ0 through the Redox Chain Reaction

An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.

Towards the Total Synthesis of Jerangolids – Synthesis of an Advanced Intermediate for the Pharmacophore Substructure

The jerangolids are a class of natural products with a skipped diene substructure isolated from Sorangium cellulosum. Here, we present a new strategy for the total synthesis of these compounds based on a skipped diyne as central building block and a suitably substituted epoxy aldehyde as building block for the dihydropyran substructure. So far, we reached an advanced intermediate which is related to the pharmacophore subunit of the jerangolids as well as of the ambruticins. A key step is a Shi epoxidation with high e.r. to form the epoxy aldehyde. Both building blocks are coupled in a Carreira alkynylation, where additional mechanistic studies based on DFT calculation were realized. The alkynylation is followed by a nucleophilic 6-endo-tet epoxide opening to form the pyran structure and a Nicholas reduction to remove a propargylic OH group.

Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Asymmetric catalysis with readily available, cheap, and non-toxic alkaline earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, we describe the development of a first MgII-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a non-innocent ligand.