18387-58-1

Basic information

• Product Name: 1-(Trimethylsilyl)-1-pentyn-3-one
• Synonyms: 1-(Trimethylsilyl)-1-pentyn-3-one;1-Pentyn-3-one, 1-(trimethylsilyl)-
• CAS NO: 18387-58-1
• Molecular Formula: C₈H₁₄OSi
• Molecular Weight: 154.08
• Mol File: 18387-58-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 168.079 °C at 760 mmHg
• Flash Point: 55.452 °C
• Appearance: /
• Density: 0.873 g/cm³
• CAS DataBase Reference: 1-(Trimethylsilyl)-1-pentyn-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(Trimethylsilyl)-1-pentyn-3-one(18387-58-1)
• EPA Substance Registry System: 1-(Trimethylsilyl)-1-pentyn-3-one(18387-58-1)

Safety Data

• Hazardous Substances Data: 18387-58-1(Hazardous Substances Data)

Usage

General Description

1-(Trimethylsilyl)-1-pentyn-3-one, also known as TMS acetylene, is a chemical compound with the molecular formula C8H16OSi. It is a reagent commonly used in organic synthesis due to its ability to add a trimethylsilyl group to various functional groups. TMS acetylene is typically utilized as a precursor for the synthesis of other more complex organic compounds, particularly in the formation of enol derivatives. It is also used as a building block in the production of pharmaceuticals and agrochemicals. Additionally, TMS acetylene is notable for its high stability and compatibility with a wide range of reaction conditions, making it a versatile and valuable reagent in organic chemistry.

Upstream product

• 79-03-8 propionyl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 88768-75-6 2-ethyl-2-(trimethylsilylethynyl)-1,3-dioxane 
• 18269-90-4 (+/-)-1-trimethylsilyl-1-pentyn-3-ol 
• 1066-54-2 trimethylsilylacetylene 
• 2975-46-4 3-(trimethylsilyl)prop-2-yn-1-al 
• 86934-41-0 2-(trimethylsilylethynyl)-1,3-dioxane 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 83182-74-5 4-Propionyl-3-phenyl-5-(trimethylsilyl)pyridazin 
• 16469-62-8 pent-1-yn-3-one 
• 13808-71-4 3-ethyl-1H-pyrazole 
• 1356145-59-9 N'-(1-(5-cyanopyrazolo[1,5-a]pyridin-3-yl)propylidene)-2-methyl-5-nitrobenzenesulfonohydrazide 
• 1356145-67-9 N'-(1-(5-cyanopyrazolo[1,5-a]pyridin-3-yl)propylidene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide 
• 865532-70-3 resolvin E2 
• 31199-03-8 1,1-dimethoxypentan-3-one 

Relevant articles and documents

Concise Total Synthesis of Ivorenolide B

An expeditious route to the potential immunosuppressive lead compound ivorenolide B (1) is described, which relies on the formation of the distinctive 1,3-diyne subunit embedded into the 17-membered framework of this target by ring-closing alkyne metathesis (RCAM). This key transformation was accomplished with the aid of the molybdenum alkylidyne complex 7, which turned out to be compatible with the acid sensitive propargylic alcohol substituents as well as the terminal alkyne unit present in the cyclization precursor. As the presence of such functionality had been detrimental for alkyne metathesis until very recently, this example illustrates the excellent application profile of this new catalyst as well as the rapidly increasing scope of the transformation. Its structural outreach can be further increased by subjecting cyclo-1,3-diynes to appropriate post-metathetic transformations, most notably with the help of alkynophilic gold or palladium catalysts. This aspect is illustrated by the conversion of the model compound 4 into various cyclophane products. Terminal, not fatal: Although the total synthesis of the immunosuppressive compound ivorenolide B (see scheme; TBS=tert-butyldimethylsilyl) relies on the cyclization of a precursor endowed with several structural elements that alkyne metathesis could not handle until recently, the macrocyclization proceeded smoothly when catalyzed by a molybdenum alkylidyne carrying silanolates as ancillary ligands. Moreover, the present study showcases how macrocyclic 1,3-diynes can be elaborated into unconventional cyclophane products.

Total synthesis and bioactivity of 18(R)-hydroxyeicosapentaenoic acid

Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic acid via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.

SULFONYL-SUBSTITUTED BICYCLIC COMPOUND WHICH ACTS AS ROR INHIBITOR

Provided is a sulfonyl-substituted bicyclic compound (A) which acts as a RORγ inhibitor, said compound has good RORγ inhibitory activity and is expected to be used for treating diseases mediated by a RORγ receptor in mammals.